3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1s,4s)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide

• ChemBase ID: 169642
• Molecular Formular: C24H34N4O5S
• Molecular Mass: 490.61556
• Monoisotopic Mass: 490.22499121
• SMILES: C(=O)(NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@@H](CC1)C)N1C(=O)C(=C(C1)C)CC
• Canonical SMILES: CCC1=C(C)CN(C1=O)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@@H](CC1)C
• InChI: InChI=1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19+
• InChIKey: WIGIZIANZCJQQY-UWUNEBHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1s,4s)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide
• IUPAC Traditional name: 3-ethyl-4-methyl-2-oxo-N-{2-[4-({[(1s,4s)-4-methylcyclohexyl]carbamoyl}aminosulfonyl)phenyl]ethyl}-5H-pyrrole-1-carboxamide
• Synonyms: cis-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(cis-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide; cis-Glimepiride

Database IDs

• CAS Number: 684286-46-2
• PubChem SID: 162263774
• PubChem CID: 3476

CALCULATED PROPERTIES

• Acid pKa: 4.3201776
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.3483384
• LogD (pH = 7.4): 2.180386
• Log P: 3.1205344
• Molar Refractivity: 129.8042 cm^3
• Polarizability: 50.725914 Å^3
• Polar Surface Area: 124.68 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 197-201°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G410145

The cis-isomer of Glimepiride found in a bulk drug substance.

REFERENCES

• Drummer, O., et al.: Anal. Toxicol., 17, 225 (1993)
• Magni, F., et al.: Anal. Biochem., 282, 136 (1993)
• Khan, M., et al.: J. Pharma. Biomed. Anal., 39, 928 (1993)