Basic information
- Standard SMILES
NC(=O)CCCN=C(c1ccc(Cl)cc1)c1cc(F)ccc1O- InChIKey
IBALRBWGSVJPAP-UHFFFAOYSA-N- Molecular formula
- C17H16ClFN2O2
- Average molar mass
- 334.8 g/mol
Overview
Progabide is a diarylmethane.
Names & identifiers
- Preferred name
- Progabide
- IUPAC
- 4-[[(4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methylidene]amino]butanamide
- English name
- Progabide
- Molecular formula
- C17H16ClFN2O2
- Molecular weight
- 334.77
Names & synonyms
Show more names
Database identifiers
- CAS
104880-78-6、62666-20-0- PubChem CID
- 44115
- DTXSID
DTXSID00878140- ChEMBL
CHEMBL287631、CHEMBL4796538- ChEBI
CHEBI:135422- UNII
- 112E50TORV、38C836J57Z
- EC Number
- 263-679-4
- Nikkaji
- J19.587A
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 75.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 425
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Nervous system -> Antiepileptics
Pharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 133 · 133-135°; mp 142.5° (Kaplan, J. Med. Chem.)
- Boiling point
- 525.4 · 525.4±50.0 °C(Predicted)
- Density
- 1.2822 · 1.2822 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly, Sonicated), DMSO, Methanol (Slightly, Sonicated)
- form
- Solid
- pka
- 3.41 · pKa 3.41 ± 0.04(0.4% MeOH,t=37,Iundefined)(Approximate)
- color
- Light Yellow to Yellow
- Water Solubility
- 37.16 mg/L · 37.16mg/L(37 ºC)
- CAS DataBase Reference
- 62666 · 62666-20-0
- FDA UNII
- 38 C836J57Z · 38C836J57Z
- ATC code
- 3 AG05 · N03AG05
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Toxicity
- 50 i.p · LD50 i.p. in mice: 900 mg/kg (Kaplan)
Safety & regulation
Toxicology
Toxicity Summary
Progabide binds to both GABA<sub>A</sub> and GABA<sub>B</sub> receptors located on the terminals of primary afferent fibers. Binding to GABA<sub>A</sub> 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<sub>B</sub> receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters.
Safety data
- Toxicity
- LD50 i.p. in mice: 900 mg/kg (Kaplan)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
Progabide binds to both GABA<sub>A</sub> and GABA<sub>B</sub> receptors located on the terminals of primary afferent fibers. Binding to GABA<sub>A</sub> 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<sub>B</sub> receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters.
Metabolism/Metabolites
Hepatic
Hepatic Half Life: 4 hours
MeSH Pharmacological Classification
Drugs used to prevent SEIZURES or reduce their severity.
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.
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.
Endogenous compounds and drugs that bind to and activate GAMMA-AMINOBUTYRIC ACID receptors (RECEPTORS, GABA).
Uses & manufacturing
Applications
DescriptionProgabide is a broad-spectrum anticonvulsant agent indicated for the treatment of a wide variety of seizure disorders. Synthesized as a GABA-prodrug, anticonvulsant activity appears due to the parent drug and its acid metabolite, as well as to GABAmide and GABA liberated therefrom.
UsesProgabide is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity.
Upstream & downstream products
Upstream raw materials
Suppliers31 total
Additional notes
DefinitionChEBI: Progabide is a diarylmethane.
Related reactions
No reaction records under the current filter.
Linked notes
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