Carisbamate

Base Information

• Chemical Name: Carisbamate
• CAS No.: 194085-75-1
• Molecular Formula: C9H10 Cl N O3
• Molecular Weight: 215.636
• UNII: P7725I9V3Z
• DSSTox Substance ID: DTXSID70426076
• Nikkaji Number: J2.736.974J
• Wikipedia: Carisbamate
• Wikidata: Q76393597
• NCI Thesaurus Code: C75161
• Metabolomics Workbench ID: 153344
• ChEMBL ID: CHEMBL2087003
• Mol file: 194085-75-1.mol

Synonyms:(S)-(1-2-chlorophenyl)-1,2-ethanediol 2-carbamate;Carisbamate;RWJ 333369;RWJ-333369;RWJ333369;S-2-O-carbamoyl-1-o-chlorophenyl-ethanol

Chemical Property of Carisbamate

Chemical Property:

• PSA: 72.55000
• LogP: 2.16900
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 215.0349209
• Heavy Atom Count: 14
• Complexity: 201

Purity/Quality:

99% ^*data from raw suppliers

(S)-Carisbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(COC(=O)N)O)Cl
• Isomeric SMILES: C1=CC=C(C(=C1)[C@@H](COC(=O)N)O)Cl
• Recent ClinicalTrials: Investigate Efficacy and Safety of Carisbamate as Adjunctive Treatment for Seizures Associated With LGS in Children and Adults
• Recent EU Clinical Trials: A Randomized, Double-blind, Placebo-Controlled Study to Investigate the Efficacy and Safety of Carisbamate (YKP509) as Adjunctive Treatment for Seizures Associated with Lennox-Gastaut Syndrome in Children and Adults, with Optional Open- Label Extension
• Description: Carisbamate is an antiepileptic agent., In vivo, administration of carisbamate (10-60 mg/kg) dose-dependently reduces spike and wave discharges in the frontoparietal cortex in a rat model of absence seizures. Carisbamate (10 mg/kg) increases latency to the first running episode in the Wistar audiogenic sensitive rat model of convulsive seizures. It also reduces motor seizure frequency in a rat model of spontaneous seizures in a dose-dependent manner. Carisbamate blocks Nav1.2 channels (IC50 = 68 μM for rat channels) and inhibits repetitive firing of action potentials in rat hippocampal neurons in a dose-dependent manner. It also reduces T-type Ca2+ currents in HEK cells transfected with human recombinant Cav3.1 channels at a concentration of 300 μM.
• Uses: Carisbamate is being developed for adjuvant treatment of partial onset epilepsy. Carisbamate produces anticonvulsant effects in primary generalized, complex partial and absence-type seizure models, an d exhibits neuroprotective and antiepileptogenic properties in rodent epilepsy models. Labelled Carisbamate; it is being developed for adjuvant treatment of partial onset epilepsy. Carisbamate produces anticonvulsant effects in primary generalized, complex partial and absence-type seizu re models, and exhibits neuroprotective and antiepileptogenic properties in rodent epilepsy models.

Technology Process of Carisbamate

There total 1 articles about Carisbamate 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:

(S)-carbamic acid 2-(2-chloro-phenyl)-2-(1-methoxy-1-methyl-ethoxy)-ethyl ester (1026550-57-1) → carisbamate (194085-75-1)

Guidance literature:

With sulfuric acid; In water; at 15 - 50 ℃; for 0.75 - 1.25h;

Reference yield:

carisbamate (194085-75-1) + toluene-4-sulfonic acid (104-15-4) → (S)-(+)-2-(2-chlorophenyl)-2-hydroxy-ethyl carbamate p-toluenesulfonic acid (1027637-67-7)

Guidance literature:

for 0.166667h; Product distribution / selectivity;

upstream raw materials:

(S)-carbamic acid 2-(2-chloro-phenyl)-2-(1-methoxy-1-methyl-ethoxy)-ethyl ester

Downstream raw materials:

(S)-(+)-2-(2-chlorophenyl)-2-hydroxy-ethyl carbamate p-toluenesulfonic acid

Refernces