5-chloro-2-methoxy-N-(2-{4-[({[(1s,4s)-4-hydroxycyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)benzamide

• ChemBase ID: 170625
• Molecular Formular: C23H28ClN3O6S
• Molecular Mass: 510.00292
• Monoisotopic Mass: 509.13873431
• SMILES: c1(ccc(c(c1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@H]1CC[C@H](CC1)O)OC)Cl
• Canonical SMILES: COc1ccc(cc1C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@@H](CC1)O)Cl
• InChI: InChI=1S/C23H28ClN3O6S/c1-33-21-11-4-16(24)14-20(21)22(29)25-13-12-15-2-9-19(10-3-15)34(31,32)27-23(30)26-17-5-7-18(28)8-6-17/h2-4,9-11,14,17-18,28H,5-8,12-13H2,1H3,(H,25,29)(H2,26,27,30)/t17-,18+
• InChIKey: IUWSGCQEWOOQDN-HDICACEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-2-methoxy-N-(2-{4-[({[(1s,4s)-4-hydroxycyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)benzamide
• IUPAC Traditional name: 5-chloro-2-methoxy-N-{2-[4-({[(1s,4s)-4-hydroxycyclohexyl]carbamoyl}aminosulfonyl)phenyl]ethyl}benzamide
• Synonyms: 5-Chloro-N-[2-[4-[[[[(cis-4-hydroxycyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide; cis-5-Chloro-N-[2-[4-[[[[(4-hydroxycyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide; rac cis-4-Hydroxy Glyburide

Database IDs

• CAS Number: 132054-81-0
• PubChem SID: 164226535
• PubChem CID: 3082214

CALCULATED PROPERTIES

• Acid pKa: 4.3201733
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.6321936
• LogD (pH = 7.4): 1.4642429
• Log P: 2.4043915
• Molar Refractivity: 128.6496 cm^3
• Polarizability: 50.19998 Å^3
• Polar Surface Area: 133.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H942630

rac cis-4-Hydroxy Glyburide is a metabolite of Glyburide used as an antidiabetic agent.

REFERENCES

• Heptner, W., et al.: Pharmaceut. Res., 5, 215 (1984)
• Rydberg, T., et al.: Br. J. Clin. Pharm., 43, 373 (1984)