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2D Structure
Also known as: 478296-72-9, Horizant, Regnite, Xp-13512, Solzira, Xp13512
Molecular Formula
C16H27NO6
Molecular Weight
329.39  g/mol
InChI Key
TZDUHAJSIBHXDL-UHFFFAOYSA-N
FDA UNII
75OCL1SPBQ

Gabapentin enacarbil is marketed under the name Horizant. It is a prodrug of gabapentin, and indicated in adults for the treatment of Restless Legs Syndrome (RLS) and postherpetic neuralgia (PHN).
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acid
2.1.2 InChI
InChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)
2.1.3 InChI Key
TZDUHAJSIBHXDL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)C(=O)OC(C)OC(=O)NCC1(CCCCC1)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
75OCL1SPBQ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(((alpha-isobutanoyloxyethoxy)carbonyl)aminomethyl)-1-cyclohexaneacetic Acid

2. Xp 10569

3. Xp 11084

4. Xp 11239

5. Xp 12464

6. Xp 13512

7. Xp-10569

8. Xp-11084

9. Xp-11239

10. Xp-12464

11. Xp-13512

12. Xp10569

13. Xp11084

14. Xp11239

15. Xp12464

16. Xp13512

2.3.2 Depositor-Supplied Synonyms

1. 478296-72-9

2. Horizant

3. Regnite

4. Xp-13512

5. Solzira

6. Xp13512

7. Asp8825

8. Xp 13512

9. Gsk1838262

10. Asp-8825

11. 75ocl1spbq

12. Gsk-1838262

13. Chebi:68840

14. 2-(1-((((1-(isobutyryloxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic Acid

15. 2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic Acid

16. {1-[({[1-(isobutyryloxy)ethoxy]carbonyl}amino)methyl]cyclohexyl}acetic Acid

17. (1-(((((1rs)-1-((2-methylpropanoyl)oxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic Acid

18. (1-{[({(1rs)-1-[isobutyryloxy]ethoxy}carbonyl) Amino]methyl}cyclohexyl)acetic Acid

19. Cyclohexaneacetic Acid, 1-((((1-(2-methyl-1-oxopropoxy)ethoxy)carbonyl)amino)methyl)-

20. Gabapentin Encarbil

21. Unii-75ocl1spbq

22. Gsk 1838262

23. Gabapentin Enacarbil [usan:inn]

24. Gabapentin-encarbil

25. Horizant (tn)

26. Asp 8825

27. Gabapentine Enacarbil

28. Gabapentina Enacarbilo

29. Gabapentinum Enacarbilum

30. Schembl25455

31. Gtpl7560

32. Chembl1628502

33. Gabapentin Encarbil [mi]

34. Dtxsid30870359

35. Gabapentin Enacarbil [inn]

36. Gabapentin Enacarbil [jan]

37. Gabapentin Enacarbil [usan]

38. Bcp12845

39. Gabapentin Enacarbil [vandf]

40. Gabapentin Enacarbil [mart.]

41. Mfcd09954124

42. Xp-053

43. Gabapentin Enacarbil [who-dd]

44. Akos025290727

45. Gabapentin Enacarbil (jan/usan/inn)

46. Cs-1698

47. Db08872

48. Pb32822

49. 1-[[[[1-(2-methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]cyclohexaneacetic Acid

50. Ncgc00532500-01

51. Ac-27644

52. As-35192

53. Gabapentin Enacarbil [orange Book]

54. Hy-16216

55. Db-070861

56. Ft-0753836

57. A20372

58. D09539

59. 296g729

60. Q5515257

61. {[(1-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane Acetic Acid

62. {[(alpha-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane Acetic Acid

63. 1-{[(alpha-isobutanovloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane Acetic Acid

64. 1-{[(alpha-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane Acetic Acid

65. 1-{[(alpha-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexaneacetic Acid

66. 2-[1-[[[1-[(2-methylpropanoyl)oxy]ethoxy]carbonylamino]methyl]cyclohexyl]acetic Acid

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 329.39 g/mol
Molecular Formula C16H27NO6
XLogP33.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass329.18383758 g/mol
Monoisotopic Mass329.18383758 g/mol
Topological Polar Surface Area102 Ų
Heavy Atom Count23
Formal Charge0
Complexity428
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameHorizant
Drug LabelHORIZANT (gabapentin enacarbil) is a prodrug of gabapentin. Gabapentin enacarbil is described as (1-{[({(1RS)-1-[(2-Methylpropanoyl)oxy]ethoxy}carbonyl)amino]methyl} cyclohexyl) acetic acid. It has a molecular formula of C16H27NO6 and a molecular wei...
Active IngredientGabapentin enacarbil
Dosage FormTablet, extended release
RouteOral
Strength600mg; 300mg
Market StatusPrescription
CompanyXenoport

2 of 2  
Drug NameHorizant
Drug LabelHORIZANT (gabapentin enacarbil) is a prodrug of gabapentin. Gabapentin enacarbil is described as (1-{[({(1RS)-1-[(2-Methylpropanoyl)oxy]ethoxy}carbonyl)amino]methyl} cyclohexyl) acetic acid. It has a molecular formula of C16H27NO6 and a molecular wei...
Active IngredientGabapentin enacarbil
Dosage FormTablet, extended release
RouteOral
Strength600mg; 300mg
Market StatusPrescription
CompanyXenoport

4.2 Drug Indication

For the treatment of adult Restless Legs Syndrome (RLS) and postherpetic neuralgia (PHN).


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Since gabapentin enacarbil is a prodrug of gabapentin, it's physiological effects are the same as gabapentin. Concerning PHN, gabapentin prevents allodynia and hyperalgesia.


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Decreased Central Nervous System Disorganized Electrical Activity [PE]; Anti-epileptic Agent [EPC]
5.3 Absorption, Distribution and Excretion

Absorption

Gabapentin enacarbil is absorbed in the intestines by active transport through the proton-linked monocarboxylate transporter, MCT-1.


Route of Elimination

Gabapentin enacarbil is eliminated primarily in the urine (94%) and to a lesser extent in the feces (5%).


Volume of Distribution

The volume of distribution is 76L.


Clearance

Renal clearance of gabapentin is 5 to 7 L/hr.


5.4 Metabolism/Metabolites

Gabapentin enacarbil does not interact with any of the major cytochrome P450 enzymes.


5.5 Biological Half-Life

The elimination half-life of gabapentin is 5.1 to 6.0 hours.


5.6 Mechanism of Action

Although the exact mechanism of action of gabapentin in RLS and PHN is unknown, it is presumed to involve the descending noradrenergic system, resulting in the activation of spinal alpha2-adrenergic receptors.