4-chloro-N-[(2R,6S)-2,6-dimethylpiperidin-1-yl]-3-sulfamoylbenzamide

• ChemBase ID: 164896
• Molecular Formular: C14H20ClN3O3S
• Molecular Mass: 345.8449
• Monoisotopic Mass: 345.0913902
• SMILES: c1(c(ccc(c1)C(=O)NN1[C@H](CCC[C@H]1C)C)Cl)S(=O)(=O)N
• Canonical SMILES: C[C@@H]1CCC[C@@H](N1NC(=O)c1ccc(c(c1)S(=O)(=O)N)Cl)C
• InChI: InChI=1S/C14H20ClN3O3S/c1-9-4-3-5-10(2)18(9)17-14(19)11-6-7-12(15)13(8-11)22(16,20)21/h6-10H,3-5H2,1-2H3,(H,17,19)(H2,16,20,21)/t9-,10+
• InChIKey: LBXHRAWDUMTPSE-AOOOYVTPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-[(2R,6S)-2,6-dimethylpiperidin-1-yl]-3-sulfamoylbenzamide
• IUPAC Traditional name: clopamide; 4-chloro-N-[(2R,6S)-2,6-dimethylpiperidin-1-yl]-3-sulfamoylbenzamide
• Synonyms: rel-3-(Aminosulfonyl)-4-chloro-N-[(2R,6S)-2,6-dimethyl-1-piperidinyl]benzamide; 4-Chloro-N-(cis-2,6-dimethylpiperidino)-3-sulfamoylbenzamide; Adurix; Aquex; Brinaldix; Chlosudimeprimyl; Clopamide; Clopamidum; DT 327; N-(cis-2',6'-Dimethyl-1'-piperidyl)-3-sulfamyl-4-chlorobenzamide; Clopamide; Chlosudimeprinyl; Clopamide

Database IDs

• CAS Number: 636-54-4
• PubChem SID: 162259030
• PubChem CID: 12492

CALCULATED PROPERTIES

• Acid pKa: 8.8533
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5865732
• LogD (pH = 7.4): 1.5734828
• Log P: 1.5867722
• Molar Refractivity: 86.1721 cm^3
• Polarizability: 34.004166 Å^3
• Polar Surface Area: 92.5 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Target: Others
• Mechanism of Action: Acts at the Proximal Convoluted tubule site of the nephron; Inhibitor of the sodium-chloride cotransport; intereferes with the reabsorption of NaCl and thus causing an equiosmolar excretion of water along with NaCl; Selectively binds at the chloride binding site of the sodium chloride cotransporter in the PCT cells on the luminal side and thus

Product Information

• Salt Data: Free Base
• Description: cis-izomers
• Application(s): Antihypertensive; Diuretic

DETAILS

Toronto Research Chemicals - C587160

Antihypertensive; diuretic.

REFERENCES

• McNeil, J.J., et al.: Clin. Pharmacol. Ther., 42, 299 (1987)
• Crowder, D., et al.: Curr. Med. Res. Opin., 6, 342 (1987)
• Jucker, E. et al., Helv. Chim. Acta, 1962, 45, 2316, (synth, ir)
• Doerling, H.J. et al., Arzneim.-Forsch., 1966, 16, 1183; 1197, (pharmacol)
• Terry, B. et al., J. Pharmacol. Exp. Ther., 1968, 160, 367, (pharmacol)
• Kracmar, J. et al., Pharmazie, 1975, 30, 447, (uv)
• McNeil, J.J. et al., Clin. Pharmacol. Ther. (St. Louis), 1987, 42, 299, (pharmacokinet)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 813