Cyclopenthiazide

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;
ECHA InfoCard	100.010.920
Chemical and physical data
Formula	C13H18ClN3O4S2
Molar mass	379.88 g/mol
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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Cyclopenthiazide (trade name Navidrex) is a thiazide diuretic used in the treatment of heart failure and hypertension.

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.

References

↑ Whitehead, C. W.; Traverso, J. J.; Sullivan, H. R.; Marshall, F. J. (1961). "Diuretics. V. 3,4-Dihydro-1,2,4-benzothiadiazine 1,1-Dioxides". The Journal of Organic Chemistry. 26 (8): 2814. doi:10.1021/jo01066a046.

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[1] Whitehead, C. W.; Traverso, J. J.; Sullivan, H. R.; Marshall, F. J. (1961). "Diuretics. V. 3,4-Dihydro-1,2,4-benzothiadiazine 1,1-Dioxides". The Journal of Organic Chemistry. 26 (8): 2814. doi:10.1021/jo01066a046.

Symporter inhibitors
Na⁺-Cl⁻	Thiazides: Bendroflumethiazide Chlorothiazide Cyclopenthiazide Cyclothiazide Hydrochlorothiazide Hydroflumethiazide Methyclothiazide Polythiazide Trichlormethiazide; Others: Chlortalidone (chlorthalidone) Metolazone
Na⁺-K⁺-Cl⁻	Bumetanide Furosemide
See also: Receptor/signaling modulators

Cyclopenthiazide

Synthesis

Contraindications

See also

References