Treating lignocellulosic materials
Abstract
It is a method for significantly reducing the region width in daily dosages required to control pain in approximately 80% of patients disclosed, wherein an oral solid dosage formulation with controlled release comprising about 10 to about 40 mg oxycodone or a salt thereof to a patient is administered. The formulation provides a mean of about 2 to about 4.5 hours after administration, a mean maximum plasma concentration of oxycodone from about 6 to about 60 ng / ml, and an average of from about 10 to about 14 hours after repeated "q12h" ( ie, every 12 hours) administration of a mean minimum plasma concentration from about 3 to about 30 ng / ml at steady state conditions. Another embodiment relates to a method for significantly reducing the region width in daily dosages required to control pain in substantially all patients. Fig. 5 is a graph showing the mean plasma oxycodone concentration of a 10 mg oxycodone controlled-release formulation as well as a Studienrefenzstandard, wherein the formulation was prepared according to the present invention.

Term
No projected expiry on record.
- Priority
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- Today
14 claims: 14 independent, 0 dependent
- 1ANSPRÜCHE EXPECTATIONS 1. A controlled release oxycodone formulation for oral administration to human patients comprising:1. Oxycodon-Formulierung mit kontrollierter Freisetzung zur oralen Verabreichung an menschliche Patienten, umfassend: (a) an oxycodone salt in an amount equivalent to 10 mg to 160 mg of the oxycodone hydrochloride salt;and (b) a controlled release dosage formulation selected from the group consisting of hydrophilic polymers, hydrophobic polymers, digestible substituted or unsubstituted hydrocarbons having 8 to 50 carbon atoms , Polyalkylene glycols and their mixtures with the exception of an acrylic resin matrix, which is selected so that the formulation has pH-independent dissolution properties, (c) the formulation having a mean maximum plasma concentration of oxycodone of 6 to 240 ng / ml 2 to 4.5 hours after administration and a mean minimum plasma concentration after repeated administration at 12 hour intervals of oxycodone from 3 to 120 ng / ml 10 to 14 hours after administration. (a) ein Oxycodonsalz in einer zu 10 mg bis 160 mg des Oxycodonhydrochloridsalzes äquivalenten Menge, und (b) eine Dosierformulierung mit kontrollierter Freisetzung, ausgewählt aus der Gruppe bestehend aus hydrophilen Polymeren, hydrophoben Polymeren, verdaubaren substituierten oder unsubstituierten Kohlenwasserstoffen mit 8 bis 50 Kohlenstoffatomen, Polyalkylenglykolen und deren Mischungen mit Ausnahme einer Acrylharzmatrix, die so ausgewählt ist, dass die Formulierung pH-unabhängige Auflösungseigenschaften aufweist, (c) wobei die Formulierung bei stationären Bedingungen nach wiederholter Verabreichung in 12 Stundenintervallen eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis 240 ng/ml 2 bis 4,5 Stunden nach Verabreichung und eine mittlere minimale Plasmakonzentration von Oxycodon von 3 bis 120 ng/ml 10 bis 14 Stunden nach Verabreichung gewährleistet.
- 2The controlled release oxycodone formulation of claim 1 comprising 10 mg to 50 mg oxycodone salt, the formulation having a mean maximum plasma concentration of oxycodone of 6 to 60 ng after repeated administration at 12 hour intervals 2 to 4.5 hours after administration / ml and after 10 to 14 hours after administration a mean minimum plasma concentration of 3 to 30 ng / ml is ensured. 2. Die Oxycodon-Formulierung mit kontrollierter Freisetzung nach Anspruch 1, umfassend 10 mg bis 50 mg Oxycodonsalz, wobei die Formulierung im stationären Zustand nach wiederholter Verabreichung in 12 Stundenintervallen 2 bis 4,5 Stunden nach Verabreichung eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis 60 ng/ml und nach 10 bis 14 Stunden nach Verabreichung eine mittlere minimale Plasmakonzentration von 3 bis 30 ng/ml gewährleistet.
- 4Oxycodon-Formulierung mit kontrollierter Freisetzung nach Anspruch 1 oder 4th The controlled release oxycodone formulation of claim 1 or claim 3, in Form einer Tablette umfassend 10 bis 160 mg Oxycodonsalz, dispergiert in einer Matrix mit kontrollierter Freisetzung. 3, in the form of a tablet comprising 10 to 160 mg of oxycodone salt dispersed in a controlled release matrix. AT 004 589 U2 AT 004 589 U2
- 5A controlled release oxycodone formulation for administration to human patients comprising:5. Oxycodon-Formulierung mit kontrollierter Freisetzung zur Verabreichung an menschliche Patienten, umfassend: (a) an analgesically effective amount of spheroids comprising oxycodone or a salt thereof and a spheronizing agent;(a) eine analgetisch wirksame Menge von Sphäroiden umfassend Oxycodon oder ein Salz davon und ein Sphäronisierjmittel;(b) each spheroid being coated with a film coating which controls the release of the oxycodone or oxycodone salt at a controlled rate in an aqueous medium. (b) wobei jedes Sphäroid mit einem Filmüberzug beschichtet ist, welches die Freisetzung des Oxycodons oder Oxycodonsalzes mit einer kontrollierten Geschwindigkeit in einem wässrigen Medium kontrolliert.
- 6Oxycodon-Formulierung mit kontrolliertre Freisetzung nach Anspruch 5, umfassend:eine analgetisch wirksame Menge von Sphäroiden umfassend ein Oxycodonsalz und ein Sphäronisierjfhfttel, so dass die Gesamtdosis des Oxycodonsalzes in der Arzneiform 10 bis 160 mg beträgt. 6th The controlled release oxycodone formulation of claim 5 comprising: an analgesically effective amount of spheroids comprising an oxycodone salt and a spheronizing agent such that the total dose of the oxycodone salt in the dosage form is 10 to 160 mg.
- 7Oxycodon-Formulierung mit kontrollierter Freisetzung nach den Ansprüchen 5 oder 6, wobei der Filmüberzug ein wasserunlösliches Material umfasst, das aus der Gruppe bestehend aus Schellack, Zein, einer wasserunlöslichen Zellulose oder ein Polymethylacrylat umfasst. 7th The controlled release oxycodone formulation of claims 5 or 6, wherein the film coating comprises a water insoluble material selected from the group consisting of shellac, zein, a water insoluble cellulose, or a polymethyl acrylate.
- 8Dosierformulierung mit kontrollierter Freisetzung nach einem der vorgenannten Ansprüche, wobei die Dosierformulierung eine In-vitroAuflösung der Arzneiform gewährleistet, die, gemessen nach der USP Paddle-Methode bei 100 UPM in 900 ml wässrigem Puffer (pH zwischen 1,6 und 7,2) bei 37°C zwischen 12,5 Gew.-% und 42,5 Gew.-% freigesetztes Oxycodon nach einer Stunde, zwischen 25 Gew.-% und 55 Gew.-% freigesetztes Oxycodon nach zwei Stunden, zwischen 45 Gew.-% und 75 Gew.-% freigesetztes Oxycodon nach 4 Stunden und zwischen 55 Gew.-% und 85 Gew.-% freigesetztes Oxycodon nach 6 Stunden aufweist, und die In-vitro-Freisetzungsgeschwindigkeit unabhängig vom pH ist, wobei im stationären Zustand nach wiederholter Verabreichung in 12 Stundenintervallen bei 2 bis 4,5 Stunden nach Verabreichung eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis 20 ng/ml erhalten wird, und nach 10 bis 14 Stunden nach Verabreichung eine mittlere minimale Plasmakonzentration von 3 bis 120 ng/ml erhalten wird. 8th. The dosage formulation with controlled release according to any one of the preceding claims, wherein the dosage formulation ensures an in vitro dissolution of the dosage form which, measured by the USP paddle method at 100 rpm in 900 ml of aqueous buffer (pH between 1.6 and 7.2) at 37 ° C between 12.5% by weight and 42.5% by weight of released oxycodone after one hour, between 25% by weight and 55% by weight of released oxycodone after two hours, between 45% by weight and 75% by weight of released oxycodone after 4 hours and between 55% by weight and 85% by weight of released oxycodone after 6 hours, and the in vitro release rate is independent of pH, wherein in the steady state after repeated administration at 12 hour intervals at 2 to 4.5 hours after administration a mean maximum plasma concentration of oxycodone of 6 to 20 ng / ml is obtained, and a mean minimum plasma concentration of 3 to 120 ng / ml is obtained after 10 to 14 hours after administration.
- 10Use of a controlled release oxycodone formulation containing oxycodone salt in a range of 10 mg to 160 mg des 10. Verwendung einer Oxycodon-Formulierung mit kontrollierter Freisetzung enthaltend Oxycodonsalz in einer zu 10 mg bis 160 mg des AT 004 589 U2 AT 004 589 U2 Hydrochloride salt equivalent amount, for the manufacture of a medicament, the medicament, when used at multiple 12-hour intervals in human patients in the stationary state, ensures:Hydrochloridsalzes äquivalenten Menge, zur Herstellung eines Medikaments, wobei das Medikament bei Anwendung in vielfachen 12-Stunden-Intervallen bei menschlichen Patienten im stationären Zustand gewährleistet: (a) a mean maximum plasma concentration of oxycodone of 6 to 240 ng / ml after 2 to 4.5 hours after administration;(a) eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis 240 ng/ml nach 2 bis 4,5 Stunden nach Verabreichung;(b) a mean minimum plasma concentration of oxycodone of 3 to 120 ng / ml after 10 to 14 hours after administration;and (c) Pain relief in essentially all human patients for at least 12 hours. (b) eine mittlere minimale Plasmakonzentration von Oxycodon von 3 bis 120 ng/ml nach 10 bis 14 Stunden nach Verabreichung;und (c) Schmerzerleichterung bei im Wesentlichen allen menschlichen Patienten für mindestens 12 Stunden. Use according to claim 10, wherein the formulation contains 10 to 40 mg of oxycodone salt, and the medicament provides in the steady state: Verwendung nach Anspruch 10, wobei die Formulierung 10 bis 40 mg Oxycodonsalz enthält, und das Medikament im stationären Zustand gewährleistet: (a) a mean maximum plasma concentration of oxycodone of 6 to 60 ng / ml after 2 to 4.5 hours after administration;(a) eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis 60 ng/ml nach 2 bis 4,5 Stunden nach Verabreichung;(b) a mean minimum plasma concentration of oxycodone of 3 to 30 ng / ml after 10 to 14 hours after administration;and (c) Pain relief in at least 90% of all human patients for at least 12 hours. (b) eine mittlere minimale Plasmakonzentration von Oxycodon von 3 bis 30 ng/ml nach 10 bis 14 Stunden nach Verabreichung;und (c) Schmerzerleichterung bei mindestens 90 % aller menschlichen Patienten für mindestens 12 Stunden.
- 1112. Verwendung einer Formulierung nach den Ansprüchen 10 oder 11, wobei das Oxycodonsalz Oxycodonhydrochlorid ist. 12th Use of a formulation according to claims 10 or 11, wherein the oxycodone salt is oxycodone hydrochloride.
- 1213. Use of a formulation according to claims 10 to 12, wherein the oxycodone salt is in a matrix. 13. Verwendung einer Formulierung nach den Ansprüchen 10 bis 12, wobei das Oxycodonsalz sich in einer Matrix befindet.
- 1314. Verwendung einer Formulierung nach den Ansprüchen 10 bis 13, wobei das Medikament für die Anwendung an einem Patienten, der unter moderaten oder schweren chronischen Schmerzen leidet, vorgesehen ist. 14th Use of a formulation according to claims 10 to 13, wherein the medicament is for use on a patient suffering from moderate or severe chronic pain.
- 1415. Verwendung einer Formulierung nach den Ansprüchen 10 bis 13, wobei das Medikament für die Anwendung bei einem Patienten, der unter postoperativen Schmerzen leidet, vorgesehen ist. 15th Use of a formulation according to claims 10 to 13, wherein the medicament is for use on a patient suffering from post-operative pain.
Independent claims14
361 paragraphs in 36 sections, as filed
Studies of daily dosages of opioid analgesics required for pain control suggest that an approximately eight-fold concentration range in daily dosages is necessary for pain control in about 90% of patients. This extraordinarily wide range in the appropriate dosage makes the titration process particularly time and material consuming and leaves the patient without acceptable pain control for an unacceptably long period of time.
In the treatment of pain with opioid analgesics, it has often been observed and reported that there is considerable inter-individual variation in response to a given dose of a given drug, and therefore considerable inter-patient variability in the dosage of opioid analgesics used for pain control with no unacceptable side effects required. This makes considerable efforts on the part of clinical staff in determining the appropriate dose in an individual patient through the time consuming titration process, which requires careful evaluation of both therapeutic and side effects, and through dose adjustments over a period of days and sometimes longer, before the appropriate one Dosage is determined. The American Pain Society's third edition of Principles of Analgesia Use in the Treatment of Acute Pain and Cancer Pain states that one should be aware that the optimal analgesic dose varies widely among patients. Research has shown that in all age groups there is an enormous
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There is variability in the doses of opioids necessary to provide relief, even from ignorant opioid patients with identical surgical injuries .... This wide variability underscores the need to prescribe analgesic procedures that include the provision of supplemental doses. and to use rapid intravenous injections and infusions to provide rapid relief from severe pain ... Subject each analgesic to adequate dose titration testing ... before switching to another active ingredient.
Opioid analgesic treatment with acceptable pain control with a much narrower daily dose range would therefore significantly improve the effectiveness and quality of pain treatment.
It was previously known in the art that controlled release compositions of opioid analgesics such as morphine, hydromorphone or their salts could be prepared in a suitable matrix. For example, U.S. Patent 4,990,341 (Goldie), also issued to the assignee of the present invention, describes hydromorphone compositions wherein the in vitro dissolution rate as measured by the USP paddle method at 100 RPM in 900 ml of aqueous buffer (pH between 1.6 and 7.2) at 37 ° C, between 12.5 and 42.5% by weight released after 1 hour, between 25 and 55% by weight released after 2 hours, between 45 and 75% by weight of hydromorphone released after 4 hours and between 55 and 85% by weight of hydromorphone released after 6 hours.
US Pat. No. 4,861,598 A and EP 0 097 523 A disclose controlled release pharmaceutical formulations.
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It is an object of the present invention to provide a method for substantially improving the effectiveness and quality of pain treatment.
It is another object of the present invention to provide an opioid analgesic formulation which significantly improves the effectiveness and quality of pain management.
It is a further object of the present invention to provide a method and formulation (s) that substantially reduce the approximately eight times the range in daily dosages necessary for pain control in approximately 90% of patients.
It is a further object of the present invention to provide a method and formulation (s) which significantly reduce the variability in daily dosages and formulation requirements necessary for pain control in essentially all patients.
It is another object of the present invention to provide a method for substantially reducing the time and resources required to titrate those patients in need of pain relief from opioid analgesics.
It is a further object of the present invention to provide controlled release opioid formulations which have substantially less inter-individual variation in the dose of opioid analgesic necessary to control pain without unacceptable side effects.
The above and other objects are achieved with the aid of the present invention, which relates to a solid oral dosage form with controlled release, which dosage form comprises about 10 mg to about 40 mg oxycodone or a salt thereof in a matrix, the in vitro dissolution rate of Dosage form, measured by the USP paddle method at 100 rpm in 900 ml of aqueous buffer (pH between 1.6 and 7.2) at 37 ° C., between 12.5 and 42.5% by weight of oxycodone released after 1 hour , between 25
AT 004 589 U2 and 56% by weight of oxycodone released after 2 hours, between 45 and 75% by weight of oxycodone released after 4 hours and between 55 and 85% by weight of oxycodone released after 6 hours, the in vitro Release rate is essentially independent of pH, so that the maximum plasma concentration of oxycodone that is achieved in vivo is reached between 2 and 4.5 hours after administration of the dosage form.
The USP paddle method is the paddle method which is described, for example, in US Pharmacopoeia XXII (1990).
In the present specification, essentially pH-independent means that the difference between the amount of oxycodone released at, for example, pH 1.6 and the amount released at any other pH, e.g. B. pH 7.2 (measured in vitro using the USP paddle method at 100 RPM in 900 ml of aqueous buffer) is 10% by weight or less at any given time. In all cases, the quantities released represent an average value from at least three experiments.
The present invention further relates to a method for substantially reducing the range of daily dosages required for pain control in approximately 90% of patients, comprising administering a solid oral
A controlled release dosage formulation comprising from about 10 to about 40 mg of oxycodone or a salt thereof, the formulation having an average maximum plasma concentration of oxycodone of about 6 to about 60 ng / ml on average from about 2 to about 4.5 hours after administration and a mean minimum plasma concentration of 3 to 30 ng / ml a mean of about 10 to about 14 hours after repeated ql2h (ie every 12 hours) administration under inpatient conditions.
The present invention further relates to a method for substantially reducing the range in daily dosages necessary for pain control in substantially all patients, comprising administering a solid oral
A controlled release dosage formulation comprising up to about 160 mg oxycodone or a salt thereof, the formulation having an average maximum plasma concentration of oxycodone up to about 240 ng / ml on average up to about 2 to
AT 004 589 U2 about 4.5 hours after administration and a mean minimum plasma concentration up to about 120 ng / ml on average from about 10 to 14 hours after repeated ql2h (ie every 12 hours) administration under stationary conditions.
The present invention further relates to controlled release oxycodone formulations comprising from about 10 to about 40 mg of oxycodone or a salt thereof, wherein the formulation has a mean maximum plasma concentration of oxycodone of about 6 to about 60 ng / ml on an average of about 2 to 4.5 hours after administration and a mean minimum plasma concentration of about 3 to about 30 ng / ml of about Deliver 10 to about 14 hours after repeated q 12h administration under stationary conditions.
The present invention further relates to controlled release oxycodone formulations comprising up to about 160 mg oxycodone or a salt thereof, the formulations having an average maximum plasma concentration of oxycodone up to about 240 ng / ml on average from about 2 to about 4.5 hours after administration and a mean minimum plasma concentration up to about 120 ng / ml from about 10 to 14 Deliver hours after repeated ql2h administration under stationary conditions.
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The following figures serve to explain the embodiments of the invention and are not intended to limit the scope of protection encompassed by the claims.
Figs. 1-4 are graphs showing time versus action curves for
Show pain intensity differences and pain relief for Example 17;
Figure 5 is a graph showing the mean plasma oxycodone concentration for a 10 mg controlled release oxycodone formulation made in accordance with the present invention and an assay reference standard.
It has now been surprisingly found that the presently claimed controlled release oxycodone formulations acceptable pain over a much narrower, approximately four-fold range (10 to 40 mg every 12 hours - round the clock dosage) in approximately 90% of patients check. This is in sharp contrast to about eight times the range generally required for about 90% of patients for opioid analgesics.
The use of about 10 mg to about 40 mg of 12 hour controlled release doses of oxycodone for pain control in about 90% of patients relative to a wider dosage range of other mp agonist analgesics indicated for moderate to severe pain is one Example of the unique properties of the present invention. It should also be recognized that the remaining 10% of patients would also be successfully treated with 12 hour controlled release doses of oxycodone over a relatively lower dosage range than with the use of other similar analgesics. Essentially all of these remaining 10%
AT 004 589 U2 of patients not being treated with 10 mg to 40 mg controlled release oxycodone every 12 hours would be treated using dosages greater than 40 mg every 12 hours to 160 mg every 12 hours, using any Number or multiples of formulation strengths, such as 10, 20, 40, 80 and 160 mg dosage units or combinations thereof. In contrast, the use of other similar analgesics, such as morphine, would require a wider dosage range to successfully treat the remaining 10% of patients. For example, daily dosages of oral morphine equivalents in the range of 1 g to greater than 20 g have been observed. Similarly, wider dosage ranges of oral hydromorphone would also be required.
Morphine, considered to be the prototype of the opioid analgesic, has been formulated in 12 hour controlled release formulations (ie, MS Contin® tablets, commercially available from Purdue Pharma, LP). Despite the fact that both controlled release oxycodone and controlled release morphine administered every 12 hours around the clock have qualitatively comparable clinical pharmacokinetic properties, the oxycodone formulations of the present claimed invention can be compared over approximately half the dosage range be used with commercially available controlled release formulations of morphine (such as MS Contin®), to control 90% of patients with significant pain.
Repeated dose studies of oxycodone formulations with controlled release administered every 12 hours compared to oral oxycodone with immediate release administered every 6 hours in the same total daily dose resulted in comparable absorption values and comparable maximum and minimum concentrations. The time of maximum concentration is reached with the controlled release product approximately 2-4.5 hours after oral administration compared to approximately 1 hour with the immediate release product. Similar repeated dose studies with MS Contin® tablets compared to immediate release morphine give comparable relative results as with the oxycodone controlled release formulations of the present invention.
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There is no substantial deviation from the parallelism of the dose-response curves for oxycodone in either the forms of the oxycodone controlled release formulations according to the present invention, oral oxycodone immediate release or parenteral oxycodone compared to oral or parenteral opioids with which Oxycodone has been compared in dose-response studies and studies of relative analgesic effectiveness. Beaver et al., Analgesie Studies of Codeine and Oxycodone in Patients with Cancer. II. Comparisons of Intramuscular Oxycodone with Intramuscular Morphine and Codeine, J. Pharmacol. and Exp. Ther., Vol. 207, No. 1, pp. 101-108, reported comparable dose-response increases for parenteral oxycodone compared to parenteral morphine and comparable dose-response increases for oral oxycodone compared to parenteral oxycodone.
An overview of dose-response studies and investigations of the relative analgesic efficacy of mp-agonistic opioid analgesics, which include oxycodone, morphine, hydromorphone, levorphanol, methadone, meperidine, heroin, shows no significant deviation from the parallelism in their dose-response relationships. This has been so well studied that it has become an underlying principle for establishing relative analgesic efficacy factors and dose ratios which are often used when switching patients from one mp-agonist analgesic to another regardless of the dosage of the former. If the dose-effect curves are not parallel, the conversion factors would not be valid over the wide range of dosages that are affected when one active substance is exchanged for another.
The clinical significance of the controlled release oxycodone formulations of the invention in a dosage range of about 10 to about 40 mg every 12 hours for acceptable pain management in about 90% of patients with moderate to severe pain when compared to other opioid analgesics, which require approximately twice the dosage range, is delivered, offers the most effective and humane method of pain management, which requires repeated dosing. The activity and time of doctors and nurses, and the duration of excruciating pain suffered by patients during the opioid analgesic titration process
AT 004 589 U2 must be considerably reduced by the efficiency of the oxycodone formulations according to the invention with controlled release.
It is also of clinical importance that a dose of about 80 mg controlled release oxycodone administered every 12 hours will provide an acceptable pain relief treatment in, for example, about 95% of patients with moderate to severe pain and that about 160 mg oxycodone controlled release, administered every 12 hours, an acceptable pain relief treatment in, e.g. will provide approximately almost all patients with moderate to severe pain.
In order to obtain a controlled release drug dosage form that has a therapeutic effect for at least 12 hours, it is common in the pharmaceutical field to prepare a formulation that achieves a maximum plasma level of the drug between approximately 4-8 hours after administration (in a single dose study) . The present inventors have surprisingly found that in the case of oxycodone a maximum plasma level between 2-4.5 hours after administration provides at least 12 hours of pain relief and, particularly surprisingly, that the pain relief achieved with such a formulation is greater than that achieved with formulations that give maximum plasma levels (of oxycodone) in the normal period of up to 2 hours after administration.
Another advantage of the present composition, which releases oxycodone at a substantially pH independent rate, is that it avoids dose delivery when administered orally. In other words, the oxycodone is released evenly through the gastrointestinal tract.
The present oral dosage form may be provided as, for example, granules, spheroids or pellets in a capsule or in any other suitable solid form. However, the oral dosage form is preferably a tablet.
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The present oral drug form preferably contains between 1 and 500 mg, in particular between 10 and 160 mg, oxycodone hydrochloride. Alternatively, the dosage form may contain equivalent amounts of other oxycodone salts or the oxycodone base.
The present matrix can be any matrix which provides in vitro dissolution rates of oxycodone within the narrow ranges required and which releases oxycodone in a pH independent manner, with the exception of an acrylic resin matrix selected so that the formulation exhibits pH independent dissolution properties . Preferably the matrix is a controlled release matrix, although normal release matrices with a coating that controls the release of the active ingredient can be used. Suitable materials for inclusion in a controlled release matrix are (a) hydrophilic polymers such as gums, cellulose ethers, acrylic resins and protein-derived materials. Of these polymers, the cellulose ethers, particularly hydroxyalkyl celluloses and carboxyalkyl celluloses, are preferred. The oral drug form can contain between 1% by weight and 80% by weight of at least one hydrophilic or hydrophobic polymer.
(b) digestible, long-chain (Cg-Cso, in particular
C12-C40), substituted or unsubstituted hydrocarbons, such as fatty acids, fatty alcohols, glyceryl esters of fatty acids, mineral and vegetable oils and waxes. Hydrocarbons with a melting point of between 25 ° C and 90 ° C are preferred. Of these long-chain hydrocarbon compounds, (aliphatic) fatty alcohols are preferred. The oral drug form can contain up to 60% by weight of at least one digestible, long-chain hydrocarbon.
(c) polyalkylene glycols. The oral drug form can contain up to 60% by weight of at least one polyalkylene glycol.
A particularly suitable matrix comprises at least one water-soluble
Hydroxyalkyl cellulose, at least one aliphatic C12-C36, preferably C14-C22, alcohol and, optionally, at least one polyalkylene glycol.
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The at least one hydroxyalkyl cellulose is preferably a hydroxy (C 1 -C 6) alkyl cellulose, such as hydroxypropyl cellulose, hydroxypropylmethyl cellulose and, in particular, hydroxyethyl cellulose. The amount of the at least one hydroxyalkyl cellulose in the present oral pharmaceutical form will be determined, among other things, by the exact rate of the required oxycodone release. However, the oral drug form preferably contains between 5% by weight and 25% by weight, in particular between 6.25% by weight and 15% by weight, of at least one hydroxyalkyl cellulose.
The at least one aliphatic alcohol can be, for example, lauryl alcohol, myristyl alcohol or stearyl alcohol. In particularly preferred embodiments of the present oral pharmaceutical form, however, the at least one aliphatic alcohol is cetyl alcohol or cetostearyl alcohol. The amount of the at least one aliphatic alcohol in the present oral dosage form will be determined, as above, by the exact rate of oxycodone release required. It will also depend on whether or not at least one polyalkylene glycol is present in the oral dosage form. In the absence of at least one polyalkylene glycol, the oral dosage form preferably contains between 20% by weight and 50% by weight of the at least one aliphatic alcohol. If at least one polyalkylene glycol is present in the oral dosage form, the combined weight of the at least one aliphatic alcohol and the at least one polyalkylene glycol is preferably between 20% by weight and 50% by weight of the total dosage.
In the presently preferred pharmaceutical form, the ratio of, for example, the at least one hydroxyalkyl cellulose to the at least one aliphatic alcohol / polyalkylene glycol determines to a considerable extent the rate of release of the oxycodone from the formulation. A ratio of the at least one hydroxyalkyl cellulose to the at least one aliphatic alcohol / polyalkylene glycol of between 1: 2 and 1: 4 is preferred, a ratio of between 1: 3 and 1: 4 being particularly preferred.
The at least one polyalkylene glycol can be, for example, polypropylene glycol or, which is preferred, polyethylene glycol. The average molecular weight of the at least one polyalkylene glycol is preferably between 1,000 and 15,000, in particular between 1,500 and 12,000.
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Another suitable controlled release matrix would be an alkyl cellulose (particularly ethyl cellulose), an aliphatic Cj<sub>2</sub> to C36 alcohol and, optionally, a polyalkylene glycol.
In addition to the above ingredients, a controlled release matrix can also contain appropriate amounts of other materials, e.g., diluents, lubricants, binders, granulating aids, colorants, flavorings and glidants, which are conventional in the pharmaceutical field.
As an alternative to a controlled release matrix, the present matrix can be a normal release matrix with a release control coating. In particularly preferred embodiments of this aspect of the invention, the present pharmaceutical form comprises film-coated spheroids which contain an active ingredient and a water-insoluble spheronizing agent. The term spheroid is known in the pharmaceutical field and has the meaning of a spherical granule with a diameter of between 0.5 mm and 2.5 mm, in particular between 0.5 mm and 2 mm.
The spheronizing agent can be any pharmaceutically acceptable material that can be spheronized with the active ingredient to form spheroids. Microcrystalline cellulose is preferred.
A suitable microcrystalline cellulose is, for example, the material sold as Avicel PH 101 (trademark, FMC Corporation). According to a preferred aspect of the present invention, the film-coated spheroids contain between 70% by weight and 99% by weight, preferably between 80% by weight and 95% by weight of the spheronizing agent, in particular microcrystalline cellulose.
In addition to the active ingredient and the spheronizing agent, the spheroids can also contain a binder. Suitable binders, such as low viscosity, water soluble polymers, will be well known to those skilled in the pharmaceutical art. However, water soluble hydroxy lower alkyl celluloses such as hydroxypropyl cellulose are preferred. Additionally (or alternatively) the spheroids can be a water-insoluble polymer,
AT 004 589 U2 contain in particular an acrylic polymer, an acrylic copolymer such as a methacrylic acid-ethyl acrylate copolymer, or ethyl cellulose.
The spheroids are preferably film-coated with a material that allows the oxycodone (or oxycodone salt) to be released at a controlled rate in an aqueous medium. The film coating is chosen so that, in combination with the other constituents, the in vitro release rate set out above is achieved (between 12.5% by weight and 42.5% by weight release after one hour, etc.).
The film coating will generally include a water-insoluble material such as (a) a wax, either alone or in admixture with a fatty alcohol, (b) shellac or zein, (c) a water-insoluble cellulose, especially ethyl cellulose, (d) a polymethacrylate, especially Eudragit®.
Preferably the film coating comprises a mixture of the water-insoluble material and a water-soluble material. The ratio of water-insoluble to water-soluble material is determined by the required release rate and the solubility properties of the selected materials, among other factors.
The water-soluble material can be, for example, polyvinylpyrrolidone or, which is preferred, a water-soluble cellulose, in particular hydroxypropylmethyl cellulose.
Suitable combinations of water-insoluble and water-soluble materials for the film coating include shellac and polyvinylpyrrolidone or, which is preferred, ethyl cellulose and hydroxypropylmethyl cellulose.
In order to facilitate the production of a solid, oral controlled release dosage form according to this invention, a further aspect of the present invention provides a method for producing a solid, oral controlled release dosage form according to the present invention, comprising the incorporation of
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Hydromorphone or a salt thereof in a controlled release matrix. The incorporation into the matrix can be effected, for example, by (a) forming granules which comprise at least one water-soluble hydroxyalkyl cellulose and oxycodone or an oxycodone salt, (b) mixing the hydroxyalkyl cellulose-containing granules with at least one aliphatic C12-C36 alcohol and (c) if necessary, pressing and shaping of the granules. Preferably the granules are formed by wet granulating hydroxyalkyl cellulose / oxycodone with water. In a particularly preferred embodiment of this process, the amount of water added during the wet granulation step is preferably between 1.5 and 5 times, preferably between 1.7 and 3.5 times, the dry weight of the oxycodone .
The present solid, oral controlled release dosage form can also be prepared in the form of film-coated spheroids by (a) mixing a mixture comprising oxycodone or an oxycodone salt and a water-insoluble spheronizing agent, (b) extruding the mixed mixture to obtain an extrudate, (c) spheronizing the extrudate until spheroids are formed; and (d) coating the spheroids with a film coating.
The present solid oral controlled release dosage form and the methods for its preparation are now described below by way of examples.
The following examples illustrate various aspects of the present invention. They are not intended to be used to limit the claims in any way.
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EXAMPLE 1
Qxycodone HCl 30 mg Controlled Release Tablets - Aqueous manufacture
The required amounts of oxycodone hydrochloride, spray-dried lactose and Eudragit® RS PM are placed in an appropriately sized mixer and mixed for approximately 5 minutes. While the powders are being mixed, the mixture is granulated with sufficient water to produce a moist, granular mass. The granules are then dried in a fluid bed dryer at 60 ° C and then passed through an 8 mesh screen. The granules are then dried again and passed through a 12 mesh screen. The required amount of stearyl alcohol is melted at about 60-70 ° C and while the granules are being mixed, the melted stearyl alcohol is added. The warm granules are returned to the mixer.
The coated granules are removed from the mixer and allowed to cool. The granules are then passed through a 12 mesh screen. The granules are then lubricated by mixing in the required amount of tallow and magnesium stearate in a suitable mixer. Tablets are compressed to a weight of 375 mg in a suitable tableting machine. The formulation for the tablets of Example 1 is shown in Table 1 below:
Table 1
Formulation of Qxycodone HCl 30-mg tablets
<td>component</td><td>mg / tablet</td><td>Wt%</td>
<td>Oxycodone hydrochloride</td><td> 30,0</td><td> 8</td>
<td>Lactose (spray dried)</td><td> 213,75</td><td> 57</td>
<td>Eudragit® RS PM</td><td> 45,0</td><td> 12</td>
<td>Purified water</td><td>qs *</td><td> —</td>
<td>Stearyl alcohol</td><td> 75,0</td><td> 20</td>
<td>Talk</td><td> 7,5</td><td> 2</td>
<td>Magnesium stearate</td><td> 3,75</td><td> 1</td>
<td>Total:</td><td> 375,0</td><td> 100</td>
* Used in production and only remains in the residual product as a residual amount.
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The tablets of Example 1 are then dissolved by means of the USP basket method, 37 ° C, 100 RPM, 700 ml gastric fluid at pH 1.2 for the first hour, then changed to
900 ml at 7.5, tested. The results are shown in Table 2 below;
Table 2
Dissolution of Oxycodone 30 mg controlled release tablets
Time% dissolved oxycodone 33J 43.5
58.2
73.2
81,8
85,8
89.2
EXAMPLE 2
Oxycodone HCl 10 mg Controlled Release Tablets - Organic manufacture
The required amounts of oxycodone hydrochloride and spray-dried lactose are placed in an appropriately sized mixer and mixed for approximately 6 minutes. About 40% of the required Eudragit® RS PM powder is dispersed in ethanol. While the powders are being mixed, the powders are granulated with the dispersion and mixing is continued until a moist granular mass is formed. Additional ethanol is added if necessary to reach the granulation end point. The granulation is transferred to a fluid bed dryer and dried at 30 ° C and then passed through a 12 mesh sieve. The remaining Eudragit® RS PM is dispersed in a solvent of 90 parts of ethanol and 10 parts of purified water and sprayed onto the granules in the fluidized bed granulator / dryer at 30 ° C. In the next step, the granulate is passed through a 12-mesh sieve. The required amount of stearyl alcohol is melted at around 60-70 ° C. The tub granules are returned to the mixer. During the
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Mixing the melted stearyl alcohol is added. The coated granules are removed from the mixer and allowed to cool. They are then passed through a 12-mesh sieve.
In the next step, the granules are lubricated by mixing the required amounts of talc and magnesium stearate in a suitable mixer. The granules are then compressed into 125 mg tablets in a suitable tableting machine.
The formulation for the tablets of Example 2 (10 mg controlled release oxycodone) is shown in Table 3 below:
Table 3
Formulation of Oxycodone HCl 10 mg controlled release tablets
<td>component</td><td>mg / tablet</td><td>Wt%</td>
<td>Oxycodone hydrochloride</td><td> 10,00</td><td> 8</td>
<td>Lactose (spray dried)</td><td> 71,25</td><td> 57</td>
<td>Eudragit® RS PM</td><td> 15,00</td><td> 12</td>
<td>Ethanol</td><td>qs *</td><td> —</td>
<td>Purified water</td><td>qs *</td><td> —</td>
<td>Stearyl alcohol</td><td> 25,00</td><td> 20</td>
<td>Talk</td><td> 2,50</td><td> 2</td>
<td>Magnesium stearate</td><td> 1,25</td><td> 1</td>
<td>Total:</td><td>125.00 mg</td><td> 100</td>
* Only used in production and only remains in the end product as a residual amount.
The tablets of Example 2 are then tested using the USP basket method at 37 ° C, 100 RPM, first hour 700 ml of simulated gastric fluid (pH 1.2), then changed to 900 ml at pH 7.5.
The results are shown in Table 4 below:
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Table 4
Dissolutions of Oxycodone 10 mg controlled release tablets
Time% dissolved oxycodone 35/9
47.7
58.5
67.7
74.5
76,9 81,2
EXAMPLES 3 - 4
Oxycodone 10 and 20 mg controlled release tablets (aqueous preparation)
Eudragit® RS 30D and Triacetin® are combined while passing through a 60 mesh screen and mixed under low shear for approximately 5 minutes or until uniform dispersion is observed.
In the next step, appropriate amounts of oxycodone HCl, lactose and povidone are added to a fluidized bed granulator / dryer (FBD) bowl and the suspension sprayed onto the powder in the fluidized bed. After spraying, the granulation is passed through a # 12 sieve, if necessary, to reduce clumps. The dry granulation is placed in a mixer.
In the meantime, the required amount of stearyl alcohol is melted at a temperature of approximately 70 ° C. The melted stearyl alcohol is incorporated into the granulation during mixing. The waxed granulation is turned into a
Fluidized bed granulator / dryer or transferred to drying trays and allowed to cool to room temperature or below. The cooled granulation is then passed through a # 12 sieve. The waxed granulation is then placed in a mixer
AT 004 589 U2 and lubricated with the required amounts of talc and magnesium stearate for about 3 minutes, after which the granules are compressed into 125 mg tablets in a suitable tableting machine.
The formulation for the tablets of Example 3 is given in Table 5 below:
Table 5
Formulation of Oxycodone 10mg Controlled Release Tablets
<td>component</td><td>mg / tablet</td><td>Wt%</td>
<td>Oxycodone hydrochloride</td><td> 10,0</td><td> 8,0</td>
<td>Lactose (spray dried)</td><td> 69,25</td><td> 55,4</td>
<td>Povidones</td><td> 5,0</td><td> 4,0</td>
<td>Eudragit® RS 30D (solid)</td><td> 10,0*</td><td> 8,0</td>
<td>Triacetin®</td><td> 2,0</td><td> 1,6</td>
<td>Stearyl alcohol</td><td> 25,0</td><td> 20,0</td>
<td>Talk</td><td> 2,5</td><td> 2,0</td>
<td>Magnesium stearate</td><td> 1,25</td><td> 1,0</td>
<td>Total:</td><td> 125,0</td><td> 100</td>
* Approximately 33.33 mg of Eutragit® RS 30D aqueous dispersion correspond to 10 mg of Eudragit® RS 30D dry substance.
The tablets of example 3 are then tested for their dissolution by means of the USP basket method at 37 ° C., 100 rpm, first hour 700 ml of simulated gastric fluid at pH 1.2, then changed to 900 ml at pH 7.5. The results are shown in Table 6 below:
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Table 6
Dissolution of Oxycodone 10 mg controlled release tablets
<td></td><td>hour</td><td>% dissolved oxycodone</td>
<td></td><td> 1</td><td> 38,0</td>
<td></td><td> 2</td><td> 47,5</td>
<td></td><td> 4</td><td> 62,0</td>
<td></td><td> 8</td><td> 79,8</td>
<td></td><td> 12</td><td> 91,1</td>
<td></td><td> 18</td><td> 94,9</td>
<td></td><td> 24</td><td> 98,7</td>
<td colspan="3">The formulation for the tablets of Example 4 is in Table 7 below</td>
<td>specified:</td><td></td><td>Table 7</td>
Formulation of Oxycodone 20mg Controlled Release Tablets
<td>component</td><td>mg / tablet</td>
<td>Oxycodone hydrochloride</td><td> 20,0</td>
<td>Lactose (spray dried)</td><td> 59,25</td>
<td>Povidones</td><td> 5,0</td>
<td>Eudragit® RS 30D (solid)</td><td> 10,0*</td>
<td>Triacetin®</td><td> 2,0</td>
<td>Stearyl alcohol</td><td> 25,0</td>
<td>Talk</td><td> 2,5</td>
<td>Magnesium stearate</td><td> 1,25</td>
<td>Total:</td><td> 125,0</td>
The tablets of Example 4 are then dissolved by means of the USP basket method at 37 ° C., 100 rpm, 700 ml of simulated gastric fluid at pH 1.2 for the first hour, then
AT 004 589 U2 changed to 900ml at pH 7.5, tested. The results are given in Table 8 below:
Table 8
Dissolution of Oxycodone 20 mg controlled release tablets
Hour% dissolved oxycodone
<td> 1</td><td> 31</td>
<td> 2</td><td> 44</td>
<td> 4</td><td> 57</td>
<td> 8</td><td> 71</td>
<td> 12</td><td> 79</td>
<td> 18</td><td> 86</td>
<td> 24</td><td> 89</td>
EXAMPLES 5-6
In Example 5, 30 mg controlled release oxycodone hydrochloride tablets are prepared according to the procedure given in Example 1.
In Example 6, 10 mg controlled release oxycodone hydrochloride tablets are prepared according to the procedure given in Example 2.
Dissolution studies of the tablets from Examples 5 and 6 are then carried out at different pH values, namely pH 1.3, 4.56, 6.88 and 7.5.
The results are provided in Tables 9 and 10 below:
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Table 9 - EXAMPLE 5
Percentage of Oxycodone HCl 30 mg tablets dissolved over time
<td>PH</td><td> 1</td><td> 2</td><td> 4</td><td> 8</td><td> 12</td><td> 18</td><td> 24</td>
<td> 1,3</td><td> 29,5</td><td> 43,7</td><td> 61,8</td><td> 78,9</td><td> 91,0</td><td> 97,0</td><td> 97,1</td>
<td> 4,56</td><td> 34,4</td><td> 49,1</td><td> 66,4</td><td> 82,0</td><td> 95,6</td><td> 99,4</td><td> 101,1</td>
<td> 6,88</td><td> 33,8</td><td> 47,1</td><td> 64,4</td><td> 81,9</td><td> 92,8</td><td> 100,5</td><td> 105,0</td>
<td> 7,5</td><td> 27,0</td><td> 38,6</td><td> 53,5</td><td> 70,0</td><td> 81,8</td><td> 89,7</td><td> 96,6</td>
<td rowspan="2"></td><td rowspan="2">Pr.</td><td rowspan="2">uzentualet</td><td>Table 10</td><td>- EXAMPLE 6</td><td rowspan="2">ig tablets,</td><td rowspan="2"></td>
<td>• Share of Oxvc</td><td>odon HCl 10 m</td>
<td></td><td></td><td></td><td>dissolved i</td><td>over time</td><td></td><td></td>
<td>PH</td><td> 1</td><td> 2</td><td> 4</td><td> 8</td><td> 12 18</td><td> 24</td>
<td> 1,3</td><td> 25,9</td><td> 41,5</td><td> 58,5</td><td> 73,5</td><td> 85,3 90,7</td><td> 94,2</td>
<td> 4,56</td><td> 37,8</td><td> 44,2</td><td> 59,4</td><td> 78,6</td><td> 88,2 91,2</td><td> 93,7</td>
<td> 6,88</td><td> 34,7</td><td> 45,2</td><td> 60,0</td><td> 75,5</td><td> 81,4 90,3</td><td> 93,9</td>
<td> 7,5</td><td> 33,2</td><td> 40,1</td><td> 51,5</td><td> 66,3</td><td> 75,2 81,7</td><td> 86,8</td>
EXAMPLES 7-12
In Examples 7-12, 4 mg and 10 mg oxycodone HCl tablets were prepared according to the formulations and procedures set forth in applicant's US Pat. No. 4,990,341.
In Example 7, oxycodone hydrochloride (10.00 g) was wet granulated with lactose monohydrate (417.5 g) and hydroxyethyl cellulose (100.00 g) and the granules were sieved through a 12 mesh sieve. The granules were then dried in a fluid bed dryer at 50 ° C and sieved through a 16 mesh screen.
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Melted cetostearyl alcohol (300.0 g) was added to the heated oxycodone-containing granules and mixed thoroughly. The mixture was air cooled, granulated again and sieved through a 16 mesh screen.
Purified talc (15.0 g) and magnesium stearate (7.5 g) were then added and mixed with the granules. The granules were then compressed into tablets.
Example 8 is prepared in the same manner as Example 7; however, the formulation contains 10 mg oxycodone HCl / tablet. The formulation for Examples 7 and 8 are given in Tables 11 and 12, respectively.
Table 11
Formulation of Example 7
Component mg / tablet g / batch
<td>Oxycodone hydrochloride</td><td> 4,0</td><td> 10,0</td>
<td>Lactose monohydrate</td><td> 167,0</td><td> 417,5</td>
<td>Hydroxyethyl cellulose</td><td> 40,0</td><td> 100,0</td>
<td>Cetostearyl alcohol</td><td> 120,0</td><td> 300,0</td>
<td>Purified talc</td><td> 6,0</td><td> 15,0</td>
<td>Magnesium stearate</td><td> 3,0</td><td> 7,5</td>
<td></td><td>Table 12</td><td></td>
Formulation of Example 8
<td>component</td><td>mg / tablet</td><td>g / approach</td>
<td>Oxycodone hydrochloride</td><td> 10,0</td><td> 25,0</td>
<td>Lactose monohydrate</td><td> 167,0</td><td> 417,5</td>
<td>Hydroxyethyl cellulose</td><td> 40,0</td><td> 100,0</td>
<td>Cetostearyl alcohol</td><td> 120,0</td><td> 300,0</td>
<td>Talk</td><td> 6,0</td><td> 15,0</td>
<td>Magnesia stearate</td><td> 3,0</td><td> 7,5</td>
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In Example 9, 4 mg oxycodone HCl controlled release tablets are prepared according to the binder formulation cited in Example 2 of US Pat. No. 4,990,341. The manufacturing process is the same as given in Examples 7 and 8 above. Example 10 is prepared according to Example 9 with the modification that 10 mg of oxycodone HCl are included per tablet. The formulations for Examples 9 and 10 are given in Tables 13 and 14, respectively.
Table 13
Formulation of Example 9
<td>component</td><td>mg / tablet</td><td>g / approach</td>
<td>Oxycodone hydrochloride</td><td> 4,0</td><td> 10,0</td>
<td>anhydrous lactose</td><td> 167,0</td><td> 417,5</td>
<td>Hydroxyethyl cellulose</td><td> 30,0</td><td> 75,0</td>
<td>Cetosteary lalkoho 1</td><td> 90,0</td><td> 225,0</td>
<td>Talk</td><td> 6,0</td><td> 15,0</td>
<td>Magnesium stearate</td><td>3.0 Table 14 Formulation of Example 10</td><td> 7,5</td>
<td>component</td><td>mg / tablet</td><td>g / approach</td>
<td>Oxycodone hydrochloride</td><td> 10,0</td><td> 25,0</td>
<td>Aqueous lactose</td><td> 167,0</td><td> 417,5</td>
<td>Hydroxyethyl cellulose</td><td> 30,0</td><td> 75,0</td>
<td>Cetostearyl alcohol</td><td> 90,0</td><td> 225,0</td>
<td>Talk</td><td> 6,0</td><td> 15,0</td>
<td>Magnesium stearate</td><td> 3,0</td><td> 7,5</td>
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In Example 11, oxycodone 4 mg controlled release tablets are made with the same binder formulation cited in Example 3 of US Patent No. 4,990,341.
Oxycodone hydrochloride (32.0 g) was wet granulated with lactose monohydrate (240.0 g), hydroxyethyl cellulose (80.0 g) and methacrylic acid copolymer (240.0 gm, Eudragit® L-100-55) and the granules were passed through a Sifted 12 mesh sieve. The granules were then dried in a fluid bed dryer at 50 ° C and passed through a 16 mesh screen.
The heated oxycodone-containing granules became molten
Cetostearyl alcohol (240.0 g) was added and mixed thoroughly. The mixture was cooled in air, granulated again and sieved through a 16 mesh screen. The granules were then compressed into tablets.
Example 12 is prepared in an identical manner to Example 11 except that 10 mg of oxycodone HCl are included per tablet. The formulations for Examples 11 and 12 are given in Tables 15 and 16, respectively.
Table 15
Formulation of Example 11
<td>component</td><td>mg / tablet</td><td>g / approach</td>
<td>Oxycodone hydrochloride</td><td> 4,0</td><td> 32,5</td>
<td>Lactose monohydrate</td><td> 30,0</td><td> 240,5</td>
<td>Hydroxyethyl cellulose</td><td> 10,0</td><td> 80,0</td>
<td>Methacrylic acid copolymer</td><td> 30,0</td><td> 240,0</td>
<td>Cetostearyl alcohol</td><td> 30,0</td><td> 240,0</td>
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Table 16
Formulation of Example 12
<td>component</td><td>mg / tablet</td><td>g / approach</td>
<td>Oxycodone hydrochloride</td><td> 10,0</td><td> 80,0</td>
<td>Lactose monohydrate</td><td> 30,0</td><td> 240,5</td>
<td>Hydroxyethyl cellulose</td><td> 10,0</td><td> 80,0</td>
<td>Methacrylic acid copolymer</td><td> 30,0</td><td> 240,0</td>
<td>Cetostearyl alcohol</td><td> 30,0</td><td> 240,0</td>
In the next step, dissolution studies were carried out with the tablets from Examples 7-12 using the USP basket method, as described in US Pharmacopoeia XXII (1990). The speed was 100 RPM, the medium was simulated gastric fluid for the first hour, followed by simulated intestinal fluid at a temperature of 37 ° C. The results are given in Table 17.
Table 17
Dissolution studies of Examples 7-12
Time% dissolved oxycodone
<td>(Hours.)</td><td>Example 7</td><td>Example 8</td><td>Ex. 9</td><td>Ex. 10</td><td>Ex. 11</td><td>Ex. 12</td>
<td> 1</td><td> 23,3</td><td> 25,5</td><td> 28,1</td><td> 29,3</td><td> 31,3</td><td> 40,9</td>
<td> 2</td><td> 35,6</td><td> 37,5</td><td> 41,5</td><td> 43,2</td><td> 44,9</td><td> 55,6</td>
<td> 4</td><td> 52,9</td><td> 56,4</td><td> 61,2</td><td> 63,6</td><td> 62,1</td><td> 74,2</td>
<td> 8</td><td> 75,3</td><td> 79,2</td><td> 83,7</td><td> 88,0</td><td> 82,0</td><td> 93,9</td>
<td> 12</td><td> 90,7</td><td> 94,5</td><td> 95,2</td><td> 100,0</td><td> 91,4</td><td> 100,0</td>
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EXAMPLES 13-16
Clinical studies
In Examples 13-16, randomized crossover bioavailability studies were carried out using the formulation of Example 2 (organic preparation) and Example 3 (aqueous preparation).
In Example 13, a single dose Fast / Fed study on 24 subjects with oxycodone tablets prepared according to Example 3 was carried out.
In Example 14, a steady-state study was carried out on 23 subjects after 12 hours with oxycodone tablets prepared according to Example 2 and compared with a 5 mg oxycodone solution with immediate release.
In Example 15, a single dose study was performed on 22 subjects using oxycodone tablets prepared according to Example 3 and compared to a 20 mg immediate release solution of oxycodone.
In Example 16, a single dose study was conducted on 12 subjects using 3x10 mg oxycodone tablets prepared according to Example 3 and compared to a 30 mg immediate release oxycodone solution.
The results of Examples 13-16 are given in Table 18.
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Table 18
<td colspan="2"></td><td>AUC</td><td>Cmax</td><td>Tmax</td>
<td>example</td><td>dosage</td><td>ng / ml / hour</td><td>ng / ml</td><td>Hours.</td>
<td> 13</td><td>10 mg CR Fast</td><td> 63</td><td> 6,1</td><td> 3,8</td>
<td></td><td>10 mg CR Fed</td><td> 68</td><td> 7,1</td><td> 3,6</td>
<td> 14</td><td>5 mg IR q6h</td><td> 121</td><td> 17</td><td> 1,2</td>
<td></td><td>10 mg CR ql2h</td><td> 130</td><td> 17</td><td> 3,2</td>
<td> 15</td><td>20 mg IR</td><td> 188</td><td> 40</td><td> 1,4</td>
<td></td><td>2x 10 mg CR</td><td> 197</td><td> 18</td><td> 2,6</td>
<td> 16</td><td>30 mg IR</td><td> 306</td><td> 53</td><td> 1,2</td>
<td></td><td>3x 10 mg CR</td><td> 350</td><td> 35</td><td> 2,6</td>
<td></td><td>30 mg CR</td><td> 352</td><td> 36</td><td> 2,9</td>
IR stands for oxycodone solution with immediate release (immediate release) CR stands for tablets with controlled release (controlled release)
EXAMPLE 17
Clinical studies
In Example 17, the relative analgesic efficacy, the tolerability and the relative duration of an oral administration of 10, 20 and 30 mg oxycodone with controlled release, prepared according to the present invention (CR OXY) and containing 15 mg were determined in a randomized single-dose double-blind study Immediate Release Oxycodone (IR OXY), 10 Immediate-release mg oxycodone in combination with 650 mg acetaminophen (IR Oxy / APAP) and placebo compared in 180 patients with moderate or severe pain following abdominal or gynecological surgery. Patients rated their pain intensity and pain relief hourly for up to 12 hours after dosing. Treatments were compared using standard scales for pain intensity and relief and onset and duration of pain relief.
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All active treatments were significantly better than placebo for many of the hourly ones
Measurements and for the sum of the pain intensity differences (SPID, sum pain intensity differences) and the total pain relief (TOTPAR, total pain relief). One
Dose response was observed under the three dose concentrations of CR OXY for
Pain relief and maximum pain intensity difference (PID) were seen, with CR OXY 20 mg and 30 mg being significantly better than the 10 mg dose. IR OXY was significantly better than CR OXY 10 mg at hours 1 and 2. IR OXY / APAP was significantly better than the 3 doses of CR OXY at hour 1 and than CR OXY 10 mg at hours 2 to 5. The time of onset was significantly shorter for the IR OXY and IR OXY / APAP treatment groups compared to the 3 CR OXY treatments. The distribution functions for the duration of pain relief showed a significantly longer duration of relief for the three CR OXY doses than for IR OXY and IR OXY / APAP. Serious adverse experiences were not reported. The results are specifically described in Table 19 below.
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Table 19
Patient disposition treatment group
IR OXY ----- CR OXY ---- 15mg PLACEBO 10mg 20mg 30mg 2Perc * total
<td>Registered and randomized to Investigative treatment</td><td> 31</td><td> 31</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 182</td>
<td>Entered the Investigative treatment phase</td><td> 31</td><td> 31</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 182</td>
<td>Complete investigation</td><td> 31</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 181</td>
<td>Aborted investigation</td><td> 0</td><td> 1</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 1</td>
<td>Excluded from the Effectiveness analysis - Vomiting before the first Hours after dosing</td><td> 0</td><td> 1</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 1</td>
<td>Unintentional help during the investigation</td><td> 1</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 0</td><td> 1</td>
<td>Analysis population: - Evaluable for security and effectiveness</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 180</td>
<td>- Evaluable for safety</td><td> 31</td><td> 31</td><td> 30</td><td> 30</td><td> 30</td><td> 30</td><td> 182</td>
* 2 Percocet® tablets
The time-response curves for pain intensity, pain intensity differences and pain relief are shown in Figures 1-4. CR OXY 10 mg
AT 004 589 U2 significantly (p <0.05) lower pain intensity values than the placebo-treated patients at 3-11 hours and lower pain values than IR OXY 15 mg and Percocet® at hour 10. CR OXY 20 mg has significantly (p <0.05) lower values Pain intensity values compared to placebo at 2-11 hours and significantly (p <0.05) lower pain values than CR OXY 10 mg, IR OXY 15 mg and Percocet at 9-11 hours. CR OXY 30 mg had significantly (p <0.05) lower pain values than placebo at 2-11 hours and lower pain values than CR OXY 10 mg at 2, 3 and 5 hours and lower values than Percocet® at hour 10.
For hourly pain relief scores, categorical and visual analog scales (CAT (categorical) and VAS (visual analog scales)), CR OXY 10 mg had significantly (p <0.05) higher pain relief scores than placebo at 3-11 hours and higher relief scores than IR OXY and Percocet® at hour 10 (and Percocet® at hour 11). CR OXY 20 mg had significantly (p <0.05) higher relief scores than placebo at 2-12 hours and higher relief scores than Percocet® at 9-12 hours. In addition, CR OXY had significantly (p <0.05) higher pain relief scores than IR OXY at 10-12 hours. CR OXY 30 mg had significantly (p <0.05) higher pain relief scores than placebo at 2-12 hours and higher scores than Percocet® at 9-12 hours and IR OXY 15 mg at hour 10.
Each treatment group was significantly (p <0.05) better than placebo in terms of the sum of the pain intensity differences (SPID) and the total pain relief (TOTPAR).
The duration of pain relief, measured by the patient stopwatch method, showed that CR OXY 10 mg, 20 mg and 30 mg had a significantly (p <0.05) longer duration of action compared to IR OXY 15 mg and 2 tablets of Percocet®. Furthermore, the three controlled release formulations showed significantly (p <0.05) longer re-treatment times compared to Percocet®.
Before retreatment, a total of 104 (57%) patients reported 120
Side effects. The most common were drowsiness, fever, dizziness, and headache.
AT 004 589 U2
On the basis of the results of this investigation, it is concluded that the controlled release oxycodone formulations according to the invention alleviate moderate to severe postoperative pain, for example as a result of abdominal or gynecological interventions in women. A dose-effect is found in the placebo <10 mg <20 mg <30 mg CR OXY as a result of a single dose. The effect occurs within an hour with maximum effects determined at 2 to 5 hours and an effect duration of 10 to 12 hours. In the case of chronic pain, steady state dosing can prolong this effect. Side effects are expected and can be easily dealt with. Headache may be dose related. Dizziness and drowsiness have been reported.
IR OXY 15 mg has an immediate maximal effect compared to controlled release oxycodone. Its duration of action is shorter (6-8 hours). Percocet® is quite effective in terms of onset of action, maximum effect and safety. The duration of action is 6-8 hours.
In summary, CR OXY was apparently an effective oral analgesic with slower onset of action but longer duration of action compared to both IR OXY and IR OXY / APAP.
EXAMPLE 18 CLINICAL TRIALS
In Example 18, a steady state crossover experiment was carried out on 21 normal male subjects and
a. CR OXY 10 mg, administered every 12 hours (ql 2h); and
b. Roxicodone® oral solution 5 mg (ROX) administered every 6 hours (q6h) were compared.
Treatment (b) was the reference standard of the investigation. The mean age was 34 years, height 176 cm and weight 75 kg. No unusual characteristics were noted about the group.
AT 004 589 U2
Figure 5 shows the average plasma oxycodone concentrations for the two formulations over the 12 hour dosing interval. The results are summarized in Table 18 in terms of averages, ratios of the averages, and 90% confidence intervals.
As a close examination of Table 18 shows, no significant differences were found between the two formulations with one exception. The only exception is the average t<sub>Max</sub> for CR OXY of 3.18 hours, which, as expected for a controlled release formulation, significantly exceeds the average ROX value of 1.38 hours. The average AUC-based bioavailability (ROX<sup>: </sup>100%) was 104.4% with 90% confidence limits of 90.9 to 117.9%. The FDA specification of ± 20% is thus met, so that the test results support the assumption that the availability of oxycodone is equally high.
AT 004 589 U2
Table 20
Summary of the pharmacokinetic parameters for oxycodone after a single dose of CR OXY (10 mg ql Oh) and ROXICODONE® in oral solution (5 mg q6h)
<td>PARAMETER</td><td>CR OXY</td><td>ROXICODONE SOLUTION</td><td>OXY / ROXI (%)</td><td>90% CI *</td>
<td>Cmax (ng / ml) ARITH. MIDDLE</td><td> 15,11</td><td> 15,57</td><td> 97,08</td><td> 85,59-108,50</td>
<td>(SD) GEOMETR.</td><td> (4,69)</td><td> (4,41)</td><td></td><td></td>
<td>MIDDLE</td><td> 14,43</td><td> 15,01</td><td> 95,14</td><td></td>
<td>Cmin (ng / ml) ARITH. MIDDLE</td><td> 6,24</td><td> 6,47</td><td> 96,41</td><td> 80,15-112,74</td>
<td>(SD) GEOMETR.</td><td> (2,64)</td><td> (3,07)</td><td></td><td></td>
<td>MIDDLE</td><td> 5,62</td><td> 5,83</td><td> 96,48</td><td></td>
<td>tmax (hrs.) ARITH. MIDDLE</td><td> 3,18</td><td> 1,38</td><td> 230,17</td><td> 160,71-298,71</td>
<td>(SD)</td><td> (2,21)</td><td> (0,71)*</td><td></td><td></td>
<td>AUC (0-12 hours) ARITH. MIDDLE</td><td> 103,50</td><td> 99,10</td><td> 104,44</td><td> 90,92-117,94</td>
<td>(SD) GEOMETR.</td><td> (40,03)</td><td> (35,04)</td><td></td><td></td>
<td>MIDDLE</td><td> 97,06</td><td> 93,97</td><td> 103,29</td><td></td>
<td>% Swing ARITH. MIDDLE</td><td> 176,36</td><td> 179,0</td><td> 98,53</td><td> 62,06-134,92</td>
<td>(SD)</td><td> (139,0)</td><td> (124,25)</td><td></td><td></td>
<td>% Fluctuation ARITH. MIDDLE</td><td> 108,69</td><td> 117,75</td><td> 92,22</td><td> 76,81-107,57</td>
<td>(SD)</td><td> (38,77)</td><td> (52,47)</td><td></td><td></td>
<td>End point ARITH. MIDDLE</td><td> -1,86</td><td> -1,86</td><td> 99,97</td><td> 117,77-22,23</td>
<td>(SD)</td><td> (2,78)</td><td> (2,19)</td><td></td><td></td>
* 90% confidence interval - considerable difference p <0.05
AT 004 589 U2
EXAMPLE 19 CLINICAL TRIALS
In Example 19, 24 normal healthy male subjects were enrolled in a randomized, single-dose, two-way crossover study to compare plasma oxycodone concentrations obtained after dosing with two oxycodone 10 mg controlled release tablets versus 20 mg (20 ml of 5 mg / ml ) of oxycodone hydrochloride solution with immediate release (IR, immediate release) can be achieved. 23 Subjects completed the investigation and were taken into account in the analysis.
Plasma oxycodone concentrations were determined using a high-performance liquidchromatography (HPLC) method. Arithmetic means C<sub>ma</sub>x, t<sub>Max</sub>, AUC and half-lives, calculated from individual plasma oxycodone concentrations versus time data, are listed in Table 21:
Table 21
<td>Pharmacological</td><td>Reference product IR</td><td>Test product CR F. (%)</td><td> 90%</td>
<td>kinetic</td><td>Oxycodone</td><td>Oxycodone 2x 10</td><td>Trust</td>
<td>parameter</td><td>20 mg</td><td>mg</td><td>interval</td>
<td>C.<sub>Max</sub> (ng / ml)</td><td> 41,60</td><td> 18,62</td><td> 44,75</td><td> 32,5-57,0</td>
<td>tmax (hrs.)</td><td> 1,30</td><td> 2,62</td><td> 200,83</td><td> 169,8-232,6</td>
<td>AUC (0-36)</td><td> 194,35</td><td> 199,62</td><td> 102,71</td><td> 89,5-115,9</td>
<td>(mg x h / ml)</td><td></td><td></td><td></td><td></td>
<td>AUC (0-)</td><td> 194,38</td><td> 208,93</td><td> 107,49</td><td> 92,9-121,9</td>
<td>(ng x hours / ml)</td><td></td><td></td><td></td><td></td>
<td>tl / 2 (elim) (hours)</td><td> 3,21</td><td> 7,98*</td><td> 249,15</td><td> 219,0-278,8</td>
<td>tl / 2 (abs) (hrs.)</td><td> 0,35</td><td> 0,92*</td><td> 264,17</td><td> 216,0-310,7</td>
<td>F.% = oral</td><td>Bioavailability</td><td></td><td></td><td></td>
CR oxycodone 2x10 mg / IR oxycodone 20 mg) * Statistically significant (p = 0.0001)
AT 004 589 U2
For C<sub>Max</sub>, t<sub>Max</sub>, ti /<sub>2</sub>(eiim) and ti / 2 (abs) there were statistically significant differences between CR Oxy and IR Oxy. There were no statistically significant differences between the two treatments in the extent of absorption [AUC (0.36), AUC (0, oo). The 90% confidence interval for CR OXY relative to IR OXY relative was 89.5% -115.9% for AUC (0.36) and 92.9% -121.9% AUC (0, oo). Based on the 90% confidence interval analysis, the oxycodone controlled release tablets were equivalent to the oxycodone immediate release solution in the extent of absorption (AUC 0.36). The controlled release absorption of oxycodone was slower by approximately 1.3 hours. No statistically significant differences were found between the two treatments for side effects, none of which were considered clinically unusual for opiates for this type of investigation.
The above studies show a significant dose-effect relationship using the oxycodone formulation according to the invention with controlled release in doses of 10, 20 and 30 mg, which do not deviate from the parallelism with dose-effect increases for MS Contin in similarly designed, well-controlled analgesic effectiveness studies by MS Contin , reported by Kaiko RS, Van Wagoner D., Brown J., et al., Controlled-Release Oral Morphine (MS Contin®Tablets, MSC) in Postoperative Pain, Pain Suppl., 5: S149 1990, which compared 30, 60, 90, and 120 mg of MS Contin versus 10 mg of intramuscular morphine and placebo, and Bloomfield, et al., Analgesia Efficacy and Potency of Two Oral Controlled-Release Morphine Preparations, Clinical Pharmacology & Therapeutics (in press), containing 30 and 90 mg of MS Contin compared to 30 and 90 mg of another oral controlled-release morphine preparation, Oramorph SR 30 mg tablets.
The examples provided above are not to be understood as exclusive examples. Many other variations of the present invention will be apparent to those skilled in the art and are included as being within the scope of the appended claims.
Contents36
5 sheets
Sheet 1 Sheet 2 Sheet 3 Sheet 4 Sheet 5
16 members in 8 offices
Priority claims3
| Document | Office | Kind | Date |
|---|---|---|---|
| 80045991 | United States of America | A | |
| 800459 | – | – | – |
| US19910800459 | – | – | – |
Members16
| Document | Office | Kind | |
|---|---|---|---|
| FI925352A0 | Finland | A0 | |
| CA2082185A1 | Canada | A1 | |
| FI925352A | Finland | A | |
| FI925352L | Finland | L | |
| BR9204539A | Brazil | A | |
| BR9204539A | Brazil | A | |
| EP0546721A1 | European Patent Office (EPO) | A1 | |
| US5374555A | United States of America | A | |
| EP0546721B1 | European Patent Office (EPO) | B1 | |
| DE69224173D1 | Germany | D1 | |
| ES2111621T3 | Spain | T3 | |
| DE69224173T2 | Germany | T2 | |
| AT4589U2This record | Austria | U2 | |
| AT4589U3 | Austria | U3 | |
| FI110698B | Finland | B | |
| CA2082185C | Canada | C |
1 legal event, as the office reported them to INPADOC
Events
| Event | Code | |
|---|---|---|
| Cancelled due to lapse of timeLapsedMN9K | MN9K |
Numbers
- Publication, DOCDB
- 4589
- Publication, EPODOC
- AT4589U
- Application
- 88000
- Application, DOCDB
- 8802000
- Application, EPODOC
- AT20000000880U
Titles2
- English
- Oxycodone COMPOSITION WITH CONTROLLED RELEASE
- German
- OXYCODON-ZUSAMMENSETZUNG MIT KONTROLLIERTER FREISETZUNG
Classification
- CPC, 3
- C12P21/06
- A61P25/04
- D21C5/005
- IPC, 4
- A61K9 26
- A61P25 04
- C12P21 06
- D21C5 00