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

• ChemBase ID: 170611
• Molecular Formular: C24H34N4O6S
• Molecular Mass: 506.61496
• Monoisotopic Mass: 506.21990583
• SMILES: c1(ccc(cc1)S(=O)(=O)NC(=O)N[C@H]1CC[C@@H](CC1)CO)CCNC(=O)N1CC(=C(C1=O)CC)C
• Canonical SMILES: OC[C@@H]1CC[C@H](CC1)NC(=O)NS(=O)(=O)c1ccc(cc1)CCNC(=O)N1CC(=C(C1=O)CC)C
• InChI: InChI=1S/C24H34N4O6S/c1-3-21-16(2)14-28(22(21)30)24(32)25-13-12-17-6-10-20(11-7-17)35(33,34)27-23(31)26-19-8-4-18(15-29)5-9-19/h6-7,10-11,18-19,29H,3-5,8-9,12-15H2,1-2H3,(H,25,32)(H2,26,27,31)/t18-,19-
• InChIKey: YUNQMQLWOOVHKI-WGSAOQKQSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 600177-94-4
• PubChem SID: 164226521
• PubChem CID: 130939

CALCULATED PROPERTIES

• LogD (pH = 7.4): 0.8216612
• Log P: 1.7618096
• Molar Refractivity: 131.6559 cm^3
• Polarizability: 51.380943 Å^3
• Polar Surface Area: 144.91 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false
• Acid pKa: 4.320178
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.9896135

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 198-200°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H942530

An active metabolite of Glimepiride.

REFERENCES

• Muller, G., et al.: Diabetes, 42, 1852 (1993)
• Kramer, W., et al.: Biochem. Biophys. Acta, 119, 278 (1993)