PROGABIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H16ClFN2O2
Molecular Weight	334.773
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)CCCN=C(C1=CC=C(Cl)C=C1)C2=C(O)C=CC(F)=C2

InChI

InChIKey=IBALRBWGSVJPAP-FXBPSFAMSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C17H16ClFN2O2
Molecular Weight	334.773
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.sciencedirect.com/science/article/pii/0223523490900204 | https://www.drugbank.ca/drugs/DB00837 | https://onlinelibrary.wiley.com/doi/full/10.1111/j.1528-1167.2009.02042.x

2,5-Dimethyl-N-Phenyl-3H-diazaphophol-4-imine is a quinonoid tautomer of GABAA and GABAB agonist progabide. According to quantum mechanical calculations, a quinonoid form is predominant in polar solvents, while aromatic tautomer is prevalent in apolar solvents. Progabide is a prodrug of gamma-aminobutyric acid and was investigated for the treatment of epilepsy, Parkinson's disease, schizophrenia, clinical depression, anxiety disorder, and other diseases. Progabide was marketed in France by Sanofi Aventis under tradename Gabrene for use in monotherapy and also as adjunctive therapy for generalized tonic-clonic, myoclonic, partial seizures, and for Lennox‐Gastaut syndrome, in both children and adults.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3432311\|https://www.ncbi.nlm.nih.gov/pubmed/7392039	Agonist 2678		40.0 µM [Ki]

PubMed

Title	Date	PubMed
[Potential therapeutic activity of GABA-mimetic drugs in neuropsychiatry].	1979	45343
Biphasic effect of direct GABA mimetic drugs on haloperidol-induced catalepsy [proceedings].	1979 Nov	574045
Effect of the new gamma-aminobutyric acid agonist SL 76 002 on striatal acetylcholine: relation to neuroleptic-induced extrapyramidal alterations.	1980	6105775
Biphasic effects of direct, but not indirect, GABA mimetics and antagonists on haloperidol-induced catalepsy.	1980 Mar	7189827
Pharmacology of the GABAergic system: effects of progabide, a GABA receptor agonist.	1984	6089242
Clinical activity of GABA agonists in neuroleptic- and L-dopa-induced dyskinesia.	1985	2860656
Anticonvulsant profile of drugs which facilitate GABAergic transmission on convulsions mediated by a GABAergic mechanism.	1986 Feb	3010161
GABA receptor agonists and extrapyramidal motor function: therapeutic implications for Parkinson's disease.	1987	3030072
Therapeutic response to progabide in neuroleptic- and L-dopa-induced dyskinesias.	1987 Jun	2900682
GABAergic modulation of lindane (gamma-hexachlorocyclohexane)-induced seizures.	1989 Aug	2474871
Co-administration of progabide inhibits haloperidol-induced oral dyskinesias in rats.	1992 Feb 25	1555638
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.	1999 Sep	10454489

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:06:02 UTC 2023` Edited by `admin` on `Fri Dec 15 17:06:02 UTC 2023`
Record UNII	38C836J57Z
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PROGABIDE

Official Name

English

GABREN

Brand Name

English

progabide [INN]

Common Name

English

BUTANAMIDE, 4-(((4-CHLOROPHENYL)(5-FLUORO-2-HYDROXYPHENYL)METHYLENE)AMINO)-

Systematic Name

English

4-((.ALPHA.-(P-CHLOROPHENYL)-5-FLUOROSALICYLIDENE)AMINO)BUTYRAMIDE

Common Name

English

PROGABIDE [MART.]

Common Name

English

Progabide [WHO-DD]

Common Name

English

PROGABIDE [USAN]

Common Name

English

SL 76 002

Code

English

PROGABIDE [MI]

Common Name

English

SL-76002

Code

English

Classification Tree Code System Code

WHO-VATC

QN03AG05