4-chloro-N-(2-methyl-1H-indol-1-yl)-3-sulfamoylbenzamide

• ChemBase ID: 165642
• Molecular Formular: C16H14ClN3O3S
• Molecular Mass: 363.81866
• Monoisotopic Mass: 363.04444
• SMILES: c1ccc2c(c1)cc(n2NC(=O)c1ccc(c(c1)S(=O)(=O)N)Cl)C
• Canonical SMILES: O=C(c1ccc(c(c1)S(=O)(=O)N)Cl)Nn1c(C)cc2c1cccc2
• InChI: InChI=1S/C16H14ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-9H,1H3,(H,19,21)(H2,18,22,23)
• InChIKey: LWCDXWWLUHMMJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-(2-methyl-1H-indol-1-yl)-3-sulfamoylbenzamide
• IUPAC Traditional name: 4-chloro-N-(2-methylindol-1-yl)-3-sulfamoylbenzamide
• Synonyms: 3-(Aminosulfonyl)-4-chloro-N-(2-methyl-1H-indol-1-yl)benzamide; 4-Chloro-3-sulfamoyl-N-(2-methyl-1H-indol-1-yl)benzamide; Dehydro Indapamide

Database IDs

• CAS Number: 63968-75-2
• PubChem SID: 162259775
• PubChem CID: 45748

CALCULATED PROPERTIES

• Acid pKa: 8.836398
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.077069
• LogD (pH = 7.4): 2.0634387
• Log P: 2.0772464
• Molar Refractivity: 94.204 cm^3
• Polarizability: 37.08988 Å^3
• Polar Surface Area: 94.19 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229660

A metabolite of Indapamide (M5). A dehydrogenation pathway by cytochromes P450.

REFERENCES

• Tamura A., et al.: Chem. Pharm. Bull., 38, 225 (1990)
• Harlow, G.R., et al.: J. Biol. Chem., 272, 5396 (1990)
• Ozden, T., et al.: Pharm. Pharmacol. Commun., 4, 397 (1990)
• Gruciani, G., et al.: J. Med. Chem., 48, 6970 (1990)
• Sun, H., et al.: Drug. Metab.