Compound: vigabatrin
SMILES: O=C(O)CCC(N)C=C
InChIKey: PJDFLNIOAUIZSL-UHFFFAOYSA-N
Synonyms: vigabatrin, 60643-86-9, 68506-86-5, Sabril, 4-Amino-5-hexenoic acid, gamma-Vinyl GABA, Vigabatrine, gamma-Vinyl-GABA, 5-Hexenoic acid, 4-amino-, gamma Vinyl GABA, Vigabatrina, Vigabatrinum, Vigabatrinum [Latin], MDL-71754, RMI-71754, gamma-Vinyl-gamma-Aminobutyric Acid, CPP-109, VIGAFYDE, MDL 71,754, DTXSID4041153, (+-)-gamma-Vinyl GABA, VINYL GAMMA-AMINOBUTYRIC ACID, GR120KRT6K, DTXCID2021153, CHEBI:63638, Vigabatrinum (Latin), gamma Vinyl gamma Aminobutyric Acid, VIGADRONE, VIGPODER, RefChem:901854, vigabatrin for oral solution, N03AG04, 4-aminohex-5-enoic acid, GVG, (+/-)-Vigabatrin, (+/-)-gamma-Vinyl GABA, CPP109, MFCD00274577, (+/-)-gamma-Vinyl-GABA, CHEMBL89598, Vigabatrine [French], (+/-)-4-aminohex-5-enoic acid, Vigabatrina [Spanish], NCGC00016087-06, Sabrilex, 4-aminohex-5-enoic acid/S(+)-Gamma-VIGABATRIN, Sabril (TN), Vigabatrin [USAN:INN:BAN], RMI-71890, MDL 71754, RMI 71754, Hexenoic acid, 4-amino, SR-01000075653, UNII-GR120KRT6K, 4-Amino-hex-5-enoic acid, Kigabeq, (+/-)-?-Vinyl GABA, rac-Vigabatrin, Vigabatrin?, Vigabatrin CRS, (1)-4-Aminohex-5-enoic acid, CPP 109, Vigabatrin [INN], Prestwick_837, -Vinyl-GABA, EINECS 270-929-6, .gamma.-vinyl GABA, .gamma.-Vinyl-GABA, Spectrum_000368, SpecPlus_000664, VIGABATRIN [MI], (y)-gamma-Vinyl GABA, VIGABATRIN [JAN], Prestwick0_000501, Prestwick1_000501, Prestwick2_000501, Prestwick3_000501, Spectrum3_001825, Vigafyde (oral solution), VIGABATRIN [USAN], (?)-gamma-Vinyl GABA, VIGABATRIN [VANDF], Biomol-NT_000247, V 8261, VIGABATRIN [MART.], VIGABATRIN [USP-RS], VIGABATRIN [WHO-DD], Lopac0_001277, M071754, SCHEMBL26714, BSPBio_000421, BSPBio_003469, KBioSS_000848, Vigabatrin (JAN/USP/INN), orb363932, (A+/-)-gamma-Vinyl GABA, DivK1c_006760, SPECTRUM1502036, SPBio_002342, ( inverted exclamation markA)-4-aminohex-5-enoic acid, BPBio1_000465, BPBio1_000925, GTPL4821, orb1310910, VIGABATRIN [ORANGE BOOK], Vinyl .gamma.-aminobutyric Acid, HSDB 8395, KBio1_001704, KBio2_000848, KBio2_003416, KBio2_005984, KBio3_002973, VIGABATRIN, (+/-)-, VIGABATRIN [EP MONOGRAPH], GLXC-05977, HMS1569F03, HMS2094M21, HMS2096F03, HMS3263P16, VIGABATRIN [USP MONOGRAPH], Tox21_110301, Tox21_501277, BDBM50118886, EBC-06162, EX-A11014, HB0868, AKOS015854596, CCG-205350, CS-0791, DB01080, FV61480, LP01277, SDCCGSBI-0051243.P004, .gamma.-Vinyl-.gamma.-aminobutyric acid, NCGC00016087-03, NCGC00016087-04, NCGC00016087-05, NCGC00016087-07, NCGC00016087-08, NCGC00016087-09, NCGC00016087-11, NCGC00016087-22, NCGC00024802-02, NCGC00024802-03, NCGC00024802-04, NCGC00024802-05, NCGC00024802-06, NCGC00261962-01, AS-11778, HY-15399, SBI-0051243.P003, ( inverted question mark)-gamma-Vinyl GABA, CAS-68506-86-5, DB-117820, AB00053309, EU-0101277, gamma-Vinyl GABA; 4-Amino-5-hexenoic acid, NS00000678, T0128, C07500, D00535, EN300-245587, AB00053309_04, Q421663, SR-01000075653-1, SR-01000075653-4, SR-01000075653-6, BRD-A07893380-001-01-6, BRD-A07893380-213-01-7, Z1255431434, Vigabatrin, European Pharmacopoeia (EP) Reference Standard, Vigabatrin, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C6H11NO2
molecular_weight: 129.16 g/mol
exact_mass: 129.078978594 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 9
topological_polar_surface_area: 63.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from acetone/water
color: Crystals from acetone/water
melting_point: 171-176C
Descriptions:
pubchem: Vigabatrin is a gamma-amino acid having a gamma-vinyl GABA structure. It is an irreversible inhibitor of gamma-aminobutyric 664 acid transaminase. It has a role as an anticonvulsant and an EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor.
chebi: A γ-amino acid having a γ-vinyl GABA structure. It is an irreversible inhibitor of γ-aminobutyric 664 acid transaminase
chembl: VIGABATRIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Vigabatrin, sold under the brand name Vigafyde among others, is a medication used in the management and treatment of infantile spasms and refractory complex partial seizures.
It works by inhibiting the breakdown of γ-aminobutyric acid (GABA). It is also known as γ-vinyl-GABA, and is a structural analogue of GABA, but does not bind to GABA receptors.
Vigabatrin is generally used only in cases of treatment-resistant epilepsy due to the risk of permanent vision loss. Although estimates of visual field loss vary substantially, risk appears to be lower among infants with treatment duration less than 12 months and the risk of clinically meaningful vision loss is very low among children treated for infantile spasms.