4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide

• ChemBase ID: 76888
• Molecular Formular: C15H15ClN2O4S
• Molecular Mass: 354.8086
• Monoisotopic Mass: 354.04410565
• SMILES: Clc1c(cc(c(c1)O)C(=O)Nc1c(cccc1C)C)S(=O)(=O)N
• Canonical SMILES: O=C(c1cc(c(cc1O)Cl)S(=O)(=O)N)Nc1c(C)cccc1C
• InChI: InChI=1S/C15H15ClN2O4S/c1-8-4-3-5-9(2)14(8)18-15(20)10-6-13(23(17,21)22)11(16)7-12(10)19/h3-7,19H,1-2H3,(H,18,20)(H2,17,21,22)
• InChIKey: MTZBBNMLMNBNJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide
• IUPAC Traditional name: xipamide
• Synonyms: 5-(Aminosulfonyl)-4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-benzamide; 4-Chloro-5-sulfamoyl-2',6'-salicyloxylidide; Aquaphor; Chronexan; Diurex; Lumitens; Xipamide; Xipamide; 4-Chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulphamoylbenzamide; 4-Chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide

Database IDs

• CAS Number: 14293-44-8
• PubChem SID: 162041788
• PubChem CID: 26618

CALCULATED PROPERTIES

• Acid pKa: 6.1722975
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.9156187
• LogD (pH = 7.4): 1.80893
• Log P: 2.9984834
• Molar Refractivity: 90.6175 cm^3
• Polarizability: 34.335552 Å^3
• Polar Surface Area: 109.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 253-254°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Irritant

Product Information

• Purity: 95+%; 97%

DETAILS

Toronto Research Chemicals - X745150

Xipamide is a diuretic and antihypertensive agent.

REFERENCES

• Wagieh, N., et al.: Drug Test. Anal., 2, 113 (2010)
• Prado-Prado, F., et al.: Bioorg. Med. Chem., 18, 2225 (2010)
• Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2010)