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Progabide

Progabide structure

CAS No:
62666-20-0
Formula:
C17H16ClFN2O2
Chemical Name:
Progabide
Synonyms:
Butanamide,4-[[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]-;4-[[(4-Chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]butanamide;SL 76-002;Progabide;Gabrene;Gabren;SL 76002;Halogabide
Categories:
Active Pharmaceutical Ingredients > Nervous System Drugs

Description

Progabide is a gamma-aminobutyric acid receptor (GABA) agonist.

Progabide is a diarylmethane.|Progabide is an analog and prodrug of gamma-aminobutyric acid. It is commonly used in the treatment of epilepsy. It has agonistic activity for both the GABAA and GABAB receptors. In clinical trials, progabide has been investigated for Parkinson's disease, schizophrenia, clinical depression and anxiety disorder; its therapeutic effectiveness in these conditions is not fully elucidated.

Progabide Basic Attributes

Molecular Weight：

334.77

Exact Mass：

334.77

EC Number：

263-679-4

UNII：

112E50TORV|38C836J57Z

ATC Code：

N - Nervous system

HScode：

2925290090

Characteristics

PSA：

72.2

XLogP3：

3.06

Density：

1.3g/cm3

Melting Point：

133-135 °C

Boiling Point：

525.363ºC at 760 mmHg

Flash Point：

271.53ºC

Refractive Index：

1.59

Water Solubility：

37.16mg/L(37 ºC)

Toxicity：

LD50 i.p. in mice: 900 mg/kg (Kaplan)

Toxicity

Protein Binding：

95%

Drug Information

Drug Indication：

Indicated for the treatment of epilepsy.

Pharmacology：

Progabide, a fatty acid derivative, is a GABA receptor agonist used to treat the symptoms of epilepsy.

MeSH：

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)|Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)|Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)|Endogenous compounds and drugs that bind to and activate GAMMA-AMINOBUTYRIC ACID receptors (RECEPTORS, GABA). (See all compounds classified as GABA Agonists.)

Absorption：

Well absorbed with a bioavailability of 60%

Metabolism/Metabolites：

Hepatic

Biological Half-Life：

4 hours

Mechanism of Action：

Progabide binds to both GABA_A and GABA_B receptors located on the terminals of primary afferent fibers. Binding to GABA_A results in an increased affinity of the GABA receptor for the amino acid, an augmented flux of chloride ions across the terminal membrane, and an increase in the amount of presynaptic inhibition. Activation of the GABA_B receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters.

MeSH Entry Terms：

Gabrene

Progabide Use and Manufacturing

Progabide is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity.

Computed Properties

Molecular Weight:334.8
XLogP3:3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:334.0884336
Monoisotopic Mass:334.0884336
Topological Polar Surface Area:75.7
Heavy Atom Count:23
Complexity:425
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Magnesium sulfate heptahydrate

Tetrahydrofuran

Cyclohexane

Sodium bicarbonate