Cyclopenthiazide

Cyclopenthiazide (trade name Navidrex) is a thiazide diuretic used in the treatment of heart failure and hypertension.

Cyclopenthiazide
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Identifiers
IUPAC name
  • 6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.920
Chemical and physical data
FormulaC13H18ClN3O4S2
Molar mass379.87 g·mol−1
3D model (JSmol)
SMILES
  • O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)NC(N2)CC3CCCC3)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)
  • Key:BKYKPTRYDKTTJY-UHFFFAOYSA-N
  (verify)

Synthesis
Cyclopenthiazide synthesis:[1]

Contraindications

Thiazide diuretics increase the excretion of sodium and potassium ions and decrease the excretion of calcium ions and uric acid so they are contraindicated in patients with hyponatraemia, hypokalaemia, hypercalcaemia and hyperuricaemia. They are also contraindicated in patients with Addison's disease.

See also

References
  1. Whitehead CW, Traverso JJ, Sullivan HR, Marshall FJ (1961). "Diuretics. V. 3,4-Dihydro-1,2,4-benzothiadiazine 1,1-Dioxides". The Journal of Organic Chemistry. 26 (8): 2814–2818. doi:10.1021/jo01066a046.


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