4-chloro-N-(5-hydroxy-2-methyl-2,3-dihydro-1H-indol-1-yl)-3-sulfamoylbenzamide

• ChemBase ID: 170669
• Molecular Formular: C16H16ClN3O4S
• Molecular Mass: 381.83394
• Monoisotopic Mass: 381.05500469
• SMILES: c1(ccc2c(c1)CC(N2NC(=O)c1ccc(c(c1)S(=O)(=O)N)Cl)C)O
• Canonical SMILES: Oc1ccc2c(c1)CC(N2NC(=O)c1ccc(c(c1)S(=O)(=O)N)Cl)C
• InChI: InChI=1S/C16H16ClN3O4S/c1-9-6-11-7-12(21)3-5-14(11)20(9)19-16(22)10-2-4-13(17)15(8-10)25(18,23)24/h2-5,7-9,21H,6H2,1H3,(H,19,22)(H2,18,23,24)
• InChIKey: ARPVNNMMMDXBBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-(5-hydroxy-2-methyl-2,3-dihydro-1H-indol-1-yl)-3-sulfamoylbenzamide
• IUPAC Traditional name: 4-chloro-N-(5-hydroxy-2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide
• Synonyms: 3-(Aminosulfonyl)-4-chloro-N-(2,3-dihydro-5-hydroxy-2-methyl-1H-indol-1-yl)benzamide; 5-Hydroxy Indapamide

Database IDs

• CAS Number: 126750-70-7
• PubChem SID: 164226579
• PubChem CID: 196806

CALCULATED PROPERTIES

• Acid pKa: 8.827607
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.33578
• LogD (pH = 7.4): 2.3217683
• Log P: 2.335979
• Molar Refractivity: 105.2943 cm^3
• Polarizability: 36.500572 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 201-204°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H943450

5-Hydroxy Indapamide is a major metabolite of Indapamide (I500100), and possesses similar antihypertensive and diuretic properties.

REFERENCES

• Slater, T., et al.: Biochem. J., 222, 1 (1984)
• Josephson, R., et al.: J. Biol. Chem., 266, 2354 (1984)
• Del Rio, M., et al.: Eur. J. Pharm., 250, 133 (1984)
• Calder, J., et al.: Eur. J. Pharma., 256, 185 (1984)