Compound: gabapentin
SMILES: O=C(O)CC1(CCCCC1)CN
InChIKey: UGJMXCAKCUNAIE-UHFFFAOYSA-N
Synonyms: gabapentin, 60142-96-3, Neurontin, 1-(Aminomethyl)cyclohexaneacetic acid, Gabapentine, 2-[1-(aminomethyl)cyclohexyl]acetic acid, Aclonium, Gabapetin, Gabapentinum, gabapentina, Gabapentino, Fanatrex, Gralise, Cyclohexaneacetic acid, 1-(aminomethyl)-, Goe-3450, 2-(1-(aminomethyl)cyclohexyl)acetic acid, CI-945, Go 3450, Gabarone, DM-1796, GOE 2450, GOE 3450, CI 945, NSC-742194, BRN 2359739, 6CW7F3G59X, DTXSID0020074, NSC-759254, DTXCID5074, CHEBI:42797, NovoGabapentin, ApoGabapentin, Apo Gabapentin, Novo Gabapentin, Gabapentin Ratiopharm, RefChem:5849, Gaba 300-EZS, 262-076-3, Serada, (1-Aminomethyl-cyclohexyl)-acetic acid, [1-(AMINOMETHYL)CYCLOHEXYL]ACETIC ACID, 1-(Aminomethyl)-cyclohexaneacetic acid, DM-5689, MFCD00865286, CHEMBL940, GABAPENTIN; NEURONTIN, Gabapen, Gabapentino [Spanish], Gabapentine [INN-French], Gabapentinum [INN-Latin], NCGC00015466-08, Gabapentino [INN-Spanish], Vultin, CAS-60142-96-3, Gabapentin GR, GBN, gabapentinium, gabapentin (Neurontin), Neuontin, Sefelsa, Gabapentin (1.0 mg/mL in Methanol), Therapentin-90, Neurontin (TN), CCRIS 7210, HSDB 7364, SR-01000000019, EINECS 262-076-3, UNII-6CW7F3G59X, Neurentin, Gabapentin?, Aclonium;, Gabapentin-ER, Novo-Gabapentine, Gabapentin CRS, Gabapentin, solid, Gabapentin [USAN:USP:INN:BAN], DDS-2003, Prestwick_151, Gralise (TN), Gabapentin free base, Gabapentin (NIST), CARBATIN, Gabapentin (Standard), Tocris-0806, GABAPENTIN [MI], Lopac-G-154, GABAPENTIN [INN], GABAPENTIN [JAN], Prestwick0_000861, Prestwick1_000861, Prestwick2_000861, Prestwick3_000861, GABAPENTIN [HSDB], GABAPENTIN [USAN], G-154, GABAPENTIN [VANDF], Gabapentin-d10, 1mg/mL, GABAPENTIN [MART.], SCHEMBL8343, GABAPENTIN [USP-RS], GABAPENTIN [WHO-DD], Lopac0_000582, BSPBio_000901, Gabapentin (JAN/USP/INN), MLS000069358, BIDD:GT0656, SPBio_002822, BPBio1_000993, GTPL5483, orb1310370, Gabapentin, 1mg/ml in Methanol, GABAPENTIN [EP IMPURITY], GABAPENTIN [ORANGE BOOK], HY-A0057R, GABAPENTIN [EP MONOGRAPH], GABAPENTIN [USP MONOGRAPH], HMS1570N03, HMS2089J03, HMS2097N03, HMS2236O03, HMS3261F06, HMS3650A20, HMS3714N03, 1-aminomethyl cyclohexaneacetic acid, 1-aminomethylcyclohexane acetic acid, HY-A0057, MSK10209, 1-(aminomethyl)cyclohexanacetic acid, Tox21_110157, Tox21_500582, BBL010794, BDBM50080153, EBC-03348, NSC742194, s2133, SBB066157, STK598009, 1-(aminomethyl)cyclohexyl-acetic Acid, AKOS000280865, Tox21_110157_1, 1-Aminomethyl-1cyclohexane-acetic acid, 2-[(aminomethyl)cyclohexyl]acetic acid, AB07485, AC-1485, CCG-204671, CS-1545, DB00996, FG23631, KS-1064, LP00582, NSC 742194, NSC 759254, SDCCGSBI-0050564.P002, 1-aminomethyl-1-cyclohexane-acetic acid, NCGC00015466-01, NCGC00015466-02, NCGC00015466-03, NCGC00015466-04, NCGC00015466-05, NCGC00015466-06, NCGC00015466-07, NCGC00015466-09, NCGC00015466-11, NCGC00015466-27, NCGC00016891-01, NCGC00021545-02, NCGC00021545-04, NCGC00021545-05, NCGC00261267-01, SMR000058311, MSK10209D10-1000, SBI-0206904.P001, AE1 - Newer Anti-epileptic drug mixtures 1, EU-0100582, G0318, NS00000335, 10B - Known Drug Blood Quantification Sample, EN300-52516, C07018, D00332, 1-(Aminomethyl)cyclohexaneacetic acid, neurontin, F040287, Gabapentin 100 microg/mL in Acetonitrile:Methanol, L000733, Q410352, SR-01000000019-2, SR-01000000019-6, BRD-K62737565-001-09-5, BRD-K62737565-001-10-3, BRD-K62737565-003-02-6, SR-01000000019-11, Z336079954, Gabapentin, European Pharmacopoeia (EP) Reference Standard, Gabapentin, United States Pharmacopeia (USP) Reference Standard, Gabapentin, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C9H17NO2
molecular_weight: 171.24 g/mol
exact_mass: 171.125928785 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 12
topological_polar_surface_area: 63.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white crystalline solid; crystals from ethanol/ether
color: White to off-white crystalline solid; crystals from ethanol/ether
melting_point: 162-166 °C; also reported as 165-167 °C
solubility: >100mg/mL
Descriptions:
{"pubchem": "Gabapentin is a gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome. It has a role as an anticonvulsant, a xenobiotic, a calcium channel blocker and an environmental contaminant. It is functionally related to a gamma-aminobutyric acid.", "chebi": "A \u03b3-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.", "chembl": "GABAPENTIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Gabapentin, sold under the brand name Neurontin among others, is an anticonvulsant medication used to treat neuropathic pain (postherpetic neuralgia) and partial seizures of epilepsy. Gabapentin is a\ncentral nervous system (CNS) depressant and derivative of the inhibitory neurotransmitter, GABA. It is used for the treatment of neuropathic pain caused by diabetic neuropathy, postherpetic neuralgia, and central pain. It is moderately effective: about 30\u201340% of those given gabapentin for diabetic neuropathy or postherpetic neuralgia have a meaningful benefit.\nGabapentin binds to \u03b12\u03b4 subunits to modulate calcium channel function and neurotransmitter release, weakly affects glutamate, and does not act on GABA receptors. Sleepiness and dizziness are the most common side effects. Serious side effects include respiratory depression and allergic reactions. On December 16, 2008, the FDA issued gabapentin a class warning for an increased risk of suicide. Approximately two years after this pronouncement, a pharmacoepidemiologic study was conducted that showed there was no outstanding difference in suicide attempt rates between pre- and post- gabapentin prescription groups.\nGabapentin was first approved for use in the United Kingdom in 1993. It has been available as a generic medication in the United States since 2004. It is the first of several other drugs that are similar in structure and mechanism, called gabapentinoids. In 2023, it was the ninth most commonly prescribed medication in the United States, with more than 45 million prescriptions. During the 1990s, Parke-Davis, a subsidiary of Pfizer, used several illegal techniques to encourage physicians in the United States to prescribe gabapentin for unapproved uses. They have paid out millions of dollars to settle lawsuits regarding these activities.\n\n"}