Progabide

Base Information

• Chemical Name: Progabide
• CAS No.: 62666-20-0
• Molecular Formula: C17H16 Cl F N2 O2
• Molecular Weight: 334.778
• Hs Code.: 2925290090
• European Community (EC) Number: 263-679-4
• UNII: 112E50TORV,38C836J57Z
• DSSTox Substance ID: DTXSID00878140
• Nikkaji Number: J19.587A
• Wikipedia: Progabide
• Wikidata: Q426524
• NCI Thesaurus Code: C166654
• ChEMBL ID: CHEMBL287631,CHEMBL4796538
• Mol file: 62666-20-0.mol

Synonyms:Gabrene;progabide;SL 76002

Chemical Property of Progabide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 133-135°; mp 142.5° (Kaplan, J. Med. Chem.)
• Boiling Point: 525.363°C at 760 mmHg
• PKA: pKa 3.41 ± 0.04(0.4% MeOH,t=37,Iundefined)(Approximate)
• Flash Point: 271.53°C
• PSA: 75.68000
• Density: 1.3g/cm³
• LogP: 3.98790
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO, Methanol (Slightly, Sonicated)
• Water Solubility.: 37.16mg/L(37 oC)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 334.0884336
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

99% ^*data from raw suppliers

Progabide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=NCCCC(=O)N)C2=C(C=CC(=C2)F)O)Cl
• Description: Progabide 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.
• Uses: Progabide is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity.

Technology Process of Progabide

There total 2 articles about Progabide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-{[1-(4-Chloro-phenyl)-1-(5-fluoro-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-butyric acid (62665-97-8) → progabide (62666-20-0)

Guidance literature:

Multistep reaction; (i) carbonyldiimidazole, THF, (ii) liq. NH₃;

Reference yield:

(4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methanone (62433-26-5) → progabide (62666-20-0)

Guidance literature:

Multi-step reaction with 2 steps

2: (i) carbonyldiimidazole, THF, (ii) liq. NH₃

Reference yield:

progabide (62666-20-0) + methyl iodide (74-88-4) → 4-{[1-(4-Chloro-phenyl)-1-(5-fluoro-2-methoxy-phenyl)-meth-(Z)-ylidene]-amino}-butyramide (72082-77-0)

Guidance literature:

Multistep reaction; (i) NaOMe, (ii) /BRN= 969135/;

upstream raw materials:

4-{[1-(4-Chloro-phenyl)-1-(5-fluoro-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-butyric acid

(4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methanone

Downstream raw materials:

4-{[1-(4-Chloro-phenyl)-1-(5-fluoro-2-methoxy-phenyl)-meth-(Z)-ylidene]-amino}-butyramide