4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanamide

• ChemBase ID: 716
• Molecular Formular: C17H16ClFN2O2
• Molecular Mass: 334.7725432
• Monoisotopic Mass: 334.08843366
• SMILES: Clc1ccc(/C(=C\2/C=C(F)C=CC2=O)/NCCCC(=O)N)cc1
• Canonical SMILES: NC(=O)CCCN/C(=C/1\C=C(F)C=CC1=O)/c1ccc(cc1)Cl
• 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/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14+
• InChIKey: DWEQWXSKOHHBNT-SAPNQHFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanamide
• IUPAC Traditional name: gabren
• Brand Name: Gabren; Gabrene
• Synonyms: Progabidum [INN-Latin]; Progabide [Usan:Ban:Inn]; Progabida [INN-Spanish]; Halogabide; Progabide

Database IDs

• CAS Number: 62666-20-0
• PubChem SID: 160964179; 46506568
• PubChem CID: 5361323

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.315554
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7826178
• LogD (pH = 7.4): 1.7963965
• Log P: 1.796575
• Molar Refractivity: 91.2219 cm^3
• Polarizability: 33.218235 Å^3
• Polar Surface Area: 72.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.68
• LOG S: -4.88
• Solubility (Water): 4.42e-03 g/l

PROPERTIES

Physical Property

• Solubility: 70.9 mg/L
• Hydrophobicity(logP): 2.6

DETAILS

DrugBank - DB00837

• Drug Groups: approved
• Description: 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. Progabide has been investigated for many diseases besides epilepsy, including Parkinson's disease, schizophrenia, clinical depression and anxiety disorder with varying success.
• 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Well absorbed with a bioavailability of 60%
• Half Life: 4 hours
• Protein Binding: 95%
• References: Bartholini G, Scatton B, Zivkovic B, Lloyd KG: GABA receptor agonists and extrapyramidal motor function: therapeutic implications for Parkinson's disease. Adv Neurol. 1987;45:79-83. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Bartholini G, Scatton B, Zivkovic B, Lloyd KG: GABA receptor agonists and extrapyramidal motor function: therapeutic implications for Parkinson's disease. Adv Neurol. 1987;45:79-83. Pubmed