6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 165238
• Molecular Formular: C13H18ClN3O4S2
• Molecular Mass: 379.88272
• Monoisotopic Mass: 379.04272575
• SMILES: c1(c(cc2c(c1)NC(NS2(=O)=O)CC1CCCC1)S(=O)(=O)N)Cl
• Canonical SMILES: Clc1cc2NC(CC3CCCC3)NS(=O)(=O)c2cc1S(=O)(=O)N
• InChI: InChI=1S/C13H18ClN3O4S2/c14-9-6-10-12(7-11(9)22(15,18)19)23(20,21)17-13(16-10)5-8-3-1-2-4-8/h6-8,13,16-17H,1-5H2,(H2,15,18,19)
• InChIKey: BKYKPTRYDKTTJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: cyclopenthiazide
• Synonyms: Navidrex; Navidrix; Salimed; Salimid; Salurilo-C; Su 8341; 6-Chloro-3-cyclopentylmethyl-7-sulfamoyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-Dioxide; Tsiklometiazid; Ultra-Minzil; Cyclopenthiazide; 6-Chloro-3-(cyclopentylmethyl)-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; Benesal; Ciba 8341-Su; Cyclomethiazide; Cyclometiazid; Cyclopentiazid; NSC 107679; Navidreks

Database IDs

• CAS Number: 742-20-1
• PubChem SID: 162259371
• PubChem CID: 2904

CALCULATED PROPERTIES

• Acid pKa: 9.06639
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.4476826
• LogD (pH = 7.4): 1.4395264
• Log P: 1.4477874
• Molar Refractivity: 88.9701 cm^3
• Polarizability: 35.532883 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C988420

Cyclopenthiazide is a thiazide diuretic. Cyclopenthiazide is used in the treatment of oedema caused by conditions such as kidney disease, liver cirrhosis and pre-menstrual syndrome as well as in the treatment of hypertension.

REFERENCES

• Davila, D. et al.: Acta Biol. Med. Exp., 5, 1(1980)
• Frenzel, J. et al.: Acta Paed. Acad. Sci. Hing., 15, 157 (1980)
• Takamura, N. et al.: Pharmac. Res., 11, 1452 (1980)