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Details for Patent: 8,906,412

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Details for Patent: 8,906,412

Title:GABA analog prodrug sustained release oral dosage forms
Abstract: Sustained release oral dosage forms of a gabapentin prodrug, 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid, are disclosed. The dosage forms are useful for treating or preventing diseases and disorders for which gabapentin is therapeutically effective.
Inventor(s): Cundy; Kenneth C. (Redwood City, CA), Sastry; Srikonda (Sunnyvale, CA), Leung; Manshiu (Daly City, CA), Kadri; Balaji V. (Tampa, FL), Stach; Paul E. (Plymouth, MN)
Assignee: XenoPort, Inc. (Santa Clara, CA)
Filing Date:Jun 19, 2014
Application Number:14/309,662
Claims:1. A method of treating ethanol withdrawal syndrome, alcohol addiction, or cocaine addiction in a patient, comprising administering to the patient in need of such treatment one or more sustained release oral tablets comprising: (a) 40 wt % to 65 wt % of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid; (b) 1 wt % to 30 wt % of glyceryl behenate; and (c) 30 wt % to 50 wt % of dibasic calcium phosphate; wherein wt % is based on the total dry weight of the dosage form, which one or more tablets: when administered to one or more fasted human patients at a dose of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from 1100 mg to 1300 mg provides a gabapentin plasma concentration profile characterized by a C.sub.max ranging from 3 .mu.g/mL to 6 .mu.g/mL, a T.sub.max ranging from 4 hours to 7 hours, and an AUC ranging from 30 .mu.ghr/mL to 70 .mu.ghr/mL; or when administered to one or more fed human patients at a dose of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from 1100 mg to 1300 mg provides a gabapentin plasma concentration profile characterized by a C.sub.max ranging from 5 .mu.g/mL to 8 .mu.g/mL, a T.sub.max ranging from 6 hours to 11 hours, and an AUC ranging from 60 .mu.ghr/mL to 110 .mu.ghr/mL.

2. The method of claim 1, wherein the one or more tablets comprise an amount of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclo- hexane acetic acid of about 600 mg.

3. The method of claim 1, wherein the one or more tablets comprise an amount of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclo- hexane acetic acid ranging from 300 mg to 700 mg.

4. The method of claim 1, wherein the 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid is in a crystalline form.

5. The method of claim 1, wherein each said tablet comprises one or more pharmaceutically acceptable excipients selected from diluents, lubricants, anti-adherents, glidants, surfactants, disintegrants, and combinations of any of the foregoing.

6. The method of claim 5, wherein the diluent is microcrystalline cellulose.

7. The method of claim 1, wherein the tablets are administered in a dose twice per day.

8. The method of claim 1, comprising a coating.

9. The method of claim 1, which when the one or more tablets are administered to the one or more fasted human patients at a dose of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from 1100 mg to 1300 mg provides a gabapentin plasma concentration profile characterized by a C.sub.max ranging from 3 .mu.g/mL to 6 .mu.g/mL, a T.sub.max ranging from 4 hours to 7 hours, and an AUC ranging from 30 .mu.ghr/mL to 70 .mu.ghr/mL; and when the one or more tablets are administered to the one or more fed human patients at a dose of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohe- xane acetic acid ranging from 1100 mg to 1300 mg provides a gabapentin plasma concentration profile characterized by a C.sub.max ranging from 5 .mu.g/mL to 8 .mu.g/mL, a T.sub.max ranging from 6 hours to 11 hours, and an AUC ranging from 60 .mu.ghr/mL to 110 .mu.ghr/mL.

10. The method of claim 1, which when the one or more tablets are administered to a population of said fasted human patients at a dose of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from a 1100 mg to 1300 mg provides a gabapentin plasma concentration profile characterized by a mean C.sub.max ranging from 3 .mu.g/mL to 6 .mu.g/mL, a mean T.sub.max ranging from 4 hours to 7 hours, and a mean AUC ranging from 30 .mu.ghr/mL to 70 .mu.ghr/mL; and when the one or more tablets are administered to a population of said fed human patients at a dose of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from 1100 mg to 1300 mg provides a gabapentin plasma concentration profile characterized by a mean C.sub.max ranging from 5 .mu.g/mL to 8 .mu.g/mL, a mean T.sub.max ranging from 6 hours to 11 hours, and a mean AUC ranging from 60 .mu.ghr/mL to 110 .mu.ghr/mL.

11. The method of claim 1, wherein: the one or more fasted human patients do not eat any food from 10 hours prior to administering the dose until 4 hours after dosing, drink 250 mL of water 2 hours and 1 hour prior to dosing and 250 mL of water a 2 hours after dosing, eat a lunch 4 hours after dosing, and eat a dinner 10 hours after dosing; and the one or more fed human patients begin eating a test meal 30 minutes prior to administering the dose and complete eating the test meal 5 minutes prior to administering the dose, eat a lunch 4 hours after dosing, and eat a dinner 10 hours after dosing, wherein the test meal comprises 1000 total calories of which 500 calories comprise fat calories.

12. The method of claim 1, wherein alcohol addiction is treated.

13. A method of treating ethanol withdrawal syndrome, alcohol addiction, or cocaine addiction in a patient, comprising administering to the patient in need of such treatment a sustained release oral tablet comprising: (a) 40 wt % to 65 wt % of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid; (b) 1 wt % to 30 wt % of glyceryl behenate; and (c) 30 wt % to 50 wt % of dibasic calcium phosphate; wherein wt % is based on the total dry weight of the tablet, which tablet when placed in 10 mM monobasic potassium phosphate buffer and 1% (wt/volume) sodium lauryl sulfate at pH 7.4 and 37.degree. C. agitated at 50 rpm (USP, Type II), releases 20% of the 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid after 2 hours, 50% after 5 hours, and 80% after 8 hours.

14. The method of claim 13, the tablet comprising an amount of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid ranging from 300 mg to 700 mg.

15. The method according to claim 13, the tablet comprising: 5 wt % to 20 wt % of microcrystalline cellulose.

16. The method of claim 13, the tablet comprising an amount of 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid of about 600 mg.

17. The method of claim 13, wherein the dosing comprises frequency of twice per day.

18. The method of claim 13, wherein alcohol addiction is treated.

19. A method of treating ethanol withdrawal syndrome, alcohol addiction, or cocaine addiction in a patient, comprising administering to the patient in need of such treatment a sustained release oral tablet, comprising: 45.8 wt % 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid; 39.56 wt % dibasic calcium phosphate; 4.58 wt % glyceryl behenate; 6.11 wt % talc; 0.41 wt % colloidal silicon dioxide; 1.84 wt % sodium lauryl sulfate; and 1.69 wt % magnesium stearate.

20. The method of claim 19, the tablet comprising 300 mg to 700 mg 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid.

21. The method of claim 19, comprising dosing at a frequency of twice per day.

22. The method of claim 19, the tablet comprising 600 mg 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid.

23. The method of claim 19, wherein alcohol addiction is treated.
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