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    Chemistry

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    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
    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

    Gabapentin Enacarbil

    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.

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 300M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 300MG

    USFDA APPLICATION NUMBER - 22399

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 600M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 600MG

    USFDA APPLICATION NUMBER - 22399

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