Cyclopenthiazide

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

Cyclopenthiazide

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	C03AA07 (WHO)
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	742-20-1
PubChem CID	2904
IUPHAR/BPS	7899
ChemSpider	2801
UNII	VX4S2N85F5
KEGG	D02061
ChEMBL	ChEMBL1373254
CompTox Dashboard (EPA)	DTXSID4022868
ECHA InfoCard	100.010.920
Chemical and physical data
Formula	C13H18ClN3O4S2
Molar mass	379.87 g·mol^−1
3D model (JSmol)	Interactive image
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
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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

• Cyclothiazide
• Hydrochlorothiazide
• Bendroflumethiazide

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.