Progabide

Progabide
Clinical data
Routes of; administration	Oral
ATC code	N03AG05 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	60%
Protein binding	95%
Metabolism	Hepatic
Elimination half-life	4 hours
Excretion	Renal
Identifiers
	IUPAC name 4-[(4-Chlorophenyl)-(5-fluoro-2-hydroxy-phenyl)-methylidene]aminobutanamide;
CAS Number	62666-20-0 ;
PubChem CID	5361323;
DrugBank	DB00837 ;
ChemSpider	10442693 ;
UNII	38C836J57Z;
ChEMBL	ChEMBL287631 ;
CompTox Dashboard (EPA)	DTXSID00878140 ;
ECHA InfoCard	100.057.872
Chemical and physical data
Formula	C17H16ClFN2O2
Molar mass	334.78 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)/C(=N\CCCC(N)=O)c2cc(F)ccc2O;
	InChI InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,22H,1-2,9H2,(H2,20,23)/b21-17+ ; Key:IBALRBWGSVJPAP-HEHNFIMWSA-N ;
	(verify)

Progabide (INN; trade name Gabrene, Sanofi-Aventis) is an analogue and prodrug of γ-aminobutyric acid (GABA) used in the treatment of epilepsy. Via conversion into GABA, progabide behaves as an agonist of the GABA_A, GABA_B, and GABA_A-ρ receptors.

Clinical data

Routes of administration	Oral
ATC code	N03AG05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	60%
Protein binding	95%
Metabolism	Hepatic
Elimination half-life	4 hours
Excretion	Renal
Identifiers
IUPAC name 4-[(4-Chlorophenyl)-(5-fluoro-2-hydroxy-phenyl)-methylidene]aminobutanamide
CAS Number	62666-20-0^Y
PubChem CID	5361323
DrugBank	DB00837^Y
ChemSpider	10442693^Y
UNII	38C836J57Z
ChEMBL	ChEMBL287631^Y
CompTox Dashboard (EPA)	DTXSID00878140
ECHA InfoCard	100.057.872
Chemical and physical data
Formula	C₁₇H₁₆ClFN₂O₂
Molar mass	334.78 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1)/C(=N\CCCC(N)=O)c2cc(F)ccc2O
InChI InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,22H,1-2,9H2,(H2,20,23)/b21-17+^Y Key:IBALRBWGSVJPAP-HEHNFIMWSA-N^Y
(verify)