(2S)-2-[2-chloro(2H4)phenyl]-2-hydroxyethyl carbamate

• ChemBase ID: 163814
• Molecular Formular: C9H10ClNO3
• Molecular Mass: 215.6336
• Monoisotopic Mass: 215.03492087
• SMILES: c1cccc(c1Cl)[C@@H](COC(=O)N)O
• Canonical SMILES: NC(=O)OC[C@H](c1ccccc1Cl)O
• InChI: InChI=1S/C9H10ClNO3/c10-7-4-2-1-3-6(7)8(12)5-14-9(11)13/h1-4,8,12H,5H2,(H2,11,13)/t8-/m1/s1
• InChIKey: OLBWFRRUHYQABZ-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[2-chloro(^2H₄)phenyl]-2-hydroxyethyl carbamate
• IUPAC Traditional name: (2S)-2-[2-chloro(^2H₄)phenyl]-2-hydroxyethyl carbamate
• Synonyms: (1S)-1-(2-Chlorophenyl-d4)-1,2-ethanediol 2-Carbamate; JNJ 10234094-d4; RWJ 333369-d4; YKP 509-d4; (S)-Carisbamate-d4

Database IDs

• PubChem SID: 162257949
• PubChem CID: 71314562

CALCULATED PROPERTIES

• Acid pKa: 13.385699
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.2871857
• LogD (pH = 7.4): 1.2871853
• Log P: 1.2871857
• Molar Refractivity: 51.4694 cm^3
• Polarizability: 20.335669 Å^3
• Polar Surface Area: 72.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C183513

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 seizure models, and exhibits neuroprotective and antiepilept

REFERENCES

• Courtney, K., et al.: J. Pharmacol. Exp. Ther., 195, 225 (1975)
• Nau, C., et al.: J. Membr. Biol., 201, 1 (1975)
• Codd, E., et al.: Pain, 134, 254 (1975)
• Francois, J., et al.: Epilepsia, 49, 393 (1975)