Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00727)
Name
Vigabatrin
Synonyms    Click to Show/Hide the Synonyms of This API
vigabatrin; 4-aminohex-5-enoic acid; Sabril; 60643-86-9; 68506-86-5; Vigabatrine; gamma-Vinyl GABA; 4-Amino-5-hexenoic acid; gamma-Vinyl-GABA; 5-Hexenoic acid, 4-amino-; Vigabatrinum; 4-Aminohexenoic acid; gamma-Vinyl-gamma-Aminobutyric Acid; MDL-71754; RMI-71754; CPP-109; CPP109; (+/-)-Vigabatrin; (R,S)-4-Amino-5-hexenoic acid; MDL 71,754; 4-Amino-hex-5-enoic acid; (+/-)-gamma-Vinyl-GABA; CHEMBL89598; CHEBI:63638; Vigabatrine [French]; Vigabatrinum [Latin]; Vigabatrina [Spanish]; VINYL GAMMA-AMINOBUTYRIC ACID; MFCD00274577; NCGC00016087-06; Vigabatrina; Sabrilex; 4-aminohex-5-enoic acid/S(+)-Gamma-VIGABATRIN; gamma Vinyl GABA; Sabril (TN); (4R)-4-aminohex-5-enoic acid; (4S)-4-aminohex-5-enoic acid; Vigabatrin [USAN:INN:BAN]; MDL 71754; RMI 71754; Hexenoic acid, 4-amino; SR-01000075653; (S)-4-Amino-5-hexenoic Acid; (+-)-gamma-Vinyl GABA; Kigabeq; MFCD00274076; (1)-4-Aminohex-5-enoic acid; CPP 109; Vigabatrin solution; Prestwick_837; EINECS 270-929-6; CAS-60643-86-9; RMI-71890; .gamma.-vinyl GABA; .gamma.-Vinyl-GABA; Spectrum_000368; SpecPlus_000664; (y)-gamma-Vinyl GABA; Prestwick0_000501; Prestwick1_000501; Prestwick2_000501; Prestwick3_000501; Spectrum3_001825; (?)-gamma-Vinyl GABA; Biomol-NT_000247; V 8261; DSSTox_CID_21153; DSSTox_RID_79637; DSSTox_GSID_41153; Lopac0_001277; M071754; SCHEMBL26714; (+/-)-gamma-Vinyl GABA; BSPBio_000421; BSPBio_003469; KBioSS_000848; Vigabatrin (JAN/USP/INN); (A+/-)-gamma-Vinyl GABA; DivK1c_006760; SPECTRUM1502036; (+/-)-?-Vinyl GABA; SPBio_002342; (+/-)-4-Aminohexenoic acid; BPBio1_000465; BPBio1_000925; GTPL4821; DTXSID4041153; Vinyl .gamma.-aminobutyric Acid; HSDB 8395; KBio1_001704; KBio2_000848; KBio2_003416; KBio2_005984; KBio3_002973; AOB6800; S(+)-4-AMINOHEXENOICACID; HMS1569F03; HMS2094M21; HMS2096F03; HMS3263P16; (plusmn)-4-aminohex-5-enoic acid; BCP16220; Tox21_110301; Tox21_501277; BDBM50118886; AKOS015854596; ACN-036276; CCG-205350; CS-0791; DB01080; LP01277; SDCCGSBI-0051243.P004; (?)-4-AMINOHEX-5-ENOIC ACID; .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; SY263247; SBI-0051243.P003; ( inverted question mark)-gamma-Vinyl GABA; AB0010729; DB-117820; AB00053309; EU-0101277; FT-0675811; FT-0675812; FT-0700968; C07500; D00535; W-5102; AB00053309_04; Q421663; Q-201924; SR-01000075653-1; SR-01000075653-4; SR-01000075653-6; ( inverted exclamation markA)-4-aminohex-5-enoic acid; BRD-A07893380-001-01-6; Z2235791448; Vigabatrin, European Pharmacopoeia (EP) Reference Standard; Vigabatrin, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Lennox-gastaut syndrome ICD-11: 8A62 [1]
PubChem CID
5665
Formula
C6H11NO2
Canonical SMILES
C=CC(CCC(=O)O)N
InChI
1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
InChIKey
PJDFLNIOAUIZSL-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
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3D MOL 2D MOL
Physicochemical Properties Molecular Weight 129.16 Topological Polar Surface Area 63.3
XlogP -2.2 Complexity 112
Heavy Atom Count 9 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Vigabatrin 500 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Titanium dioxide; Povidone; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Lundbeck Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved vigabatrin from the official website of the U.S. Food and Drug Administration.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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