Compound: Gabapentin enacarbil
SMILES: O=C(OC(OC(=O)C(C)C)C)NCC1(CCCCC1)CC(=O)O
InChIKey: TZDUHAJSIBHXDL-UHFFFAOYSA-N
Synonyms: Gabapentin enacarbil, 478296-72-9, Horizant, Regnite, XP-13512, XP13512, ASP8825, gabapentine enacarbil, XP 13512, gabapentina enacarbilo, GSK1838262, 75OCL1SPBQ, ASP-8825, GSK-1838262, gabapentinum enacarbilum, 2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acid, CHEBI:68840, DTXSID30870359, {1-[({[1-(isobutyryloxy)ethoxy]carbonyl}amino)methyl]cyclohexyl}acetic acid, Gabapentinenacarbil, (1-(((((1RS)-1-((2-methylpropanoyl)oxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic acid, Cyclohexaneacetic acid, 1-((((1-(2-methyl-1-oxopropoxy)ethoxy)carbonyl)amino)methyl)-, (1-((((1-(isobutyryloxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic acid, (1-{[({(1RS)-1-[(2-Methylpropanoyl)oxy]ethoxy}carbonyl)amino]methyl}cyclohexyl)acetic acid, 2-(1-((1-(2-methylpropanoyloxy)ethoxycarbonylamino)methyl)cyclohexyl)acetic acid, cyclohexaneacetic acid, 1-[[[[1-(2-methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]-, RefChem:55240, DTXCID30818094, Solzira, 2-(1-((((1-(Isobutyryloxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic acid, MFCD09954124, Gabapentin Encarbil, UNII-75OCL1SPBQ, GSK 1838262, Gabapentin enacarbil [USAN:INN], Gabapentin-Encarbil, Horizant (TN), ASP 8825, Gabapentin enacarbil [MI], 1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]cyclohexaneacetic acid, SCHEMBL25455, GTPL7560, orb3029192, CHEMBL1628502, TZDUHAJSIBHXDL-UHFFFAOYSA-N, GABAPENTIN ENACARBIL [INN], GABAPENTIN ENACARBIL [JAN], GLXC-07660, GABAPENTIN ENACARBIL [USAN], GABAPENTIN ENACARBIL [VANDF], EBC-26609, GABAPENTIN ENACARBIL [MART.], XP-053, GABAPENTIN ENACARBIL [WHO-DD], AKOS025290727, Gabapentin enacarbil (JAN/USAN/INN), CS-1698, DB08872, FG31551, PB32822, (1-{[({(1RS)-1-[isobutyryloxy]ethoxy}carbonyl) amino]methyl}cyclohexyl)acetic acid, 2-(1-{[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]methyl}cyclohexyl)acetic acid, NCGC00532500-01, AC-27644, AS-35192, GABAPENTIN ENACARBIL [ORANGE BOOK], HY-16216, DB-070861, NS00000149, D09539, EN300-7418747, F512708, Q5515257, BRD-A86665761-001-01-1, {[(1-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid, 1-[[(1-(Isobutanoyloxy)ethoxy)carbonyl]aminomethyl]cyclohex-1-ylacetic acid, (1-{[({1-[(2-Methylpropanoyl)oxy]ethoxy}carbonyl)amino]methyl}cyclohexyl)acetic acid, {[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid, 1-{[(alpha-Isobutanovloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid, 1-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid, 1-{[(alpha-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexaneacetic acid
Theoretical properties:
molecular_formula: C16H27NO6
molecular_weight: 329.39 g/mol
exact_mass: 329.18383758 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 9
heavy_atom_count: 23
topological_polar_surface_area: 102 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: Melting onset of about 64°C.
solubility: Solubility of 0.5 mg/mL in water
Descriptions:
{"pubchem": "Gabapentin enacarbil is a carbamate ester that is the N-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic pain and restless legs syndrome. It has a role as an anticonvulsant, a calcium channel blocker and a prodrug. It is a carbamate ester, a monocarboxylic acid, a carboxylic ester and an acetal. It is functionally related to a gamma-aminobutyric acid and a gabapentin.", "chebi": "A carbamate ester that is the <em>N</em>-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic pain and restless legs syndrome.", "chembl": "GABAPENTIN ENACARBIL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Gabapentin enacarbil, sold under the brand name Horizant, among others, is an anticonvulsant and analgesic drug of the gabapentinoid class, and a prodrug to gabapentin. It was designed for increased oral bioavailability over gabapentin, and human trials showed it to produce extended release of gabapentin with almost twice the overall bioavailability, especially when taken with a fatty meal. Gabapentin enacarbil has passed human clinical trials for the treatment of restless legs syndrome, and initial results have shown it to be well tolerated and reasonably effective.\nGabapentin enacarbil was denied approval by the US Food and Drug Administration (FDA) in February 2010, citing concerns about possible increased cancer risk shown by some animal studies. Similar concerns had been raised about gabapentin itself in the past, but were felt to be outweighed by its clinical utility as an anticonvulsant, whereas the treatment of restless legs syndrome was not seen to justify the same kind of risk. On 6 April 2011, Xenoport received FDA approval for Horizant (gabapentin enacarbil) for the treatment of moderate-to-severe restless legs syndrome. On 7 June 2012, the FDA approved Horizant for the treatment of postherpetic neuralgia in adults."}