Cyclopenthiazide

Cyclopenthiazide
Systematic (IUPAC) name

6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	UK: POM (Prescription only)
Identifiers
CAS Number	742-20-1
ATC code	C03AA07
PubChem	CID 2904
IUPHAR/BPS	7899
ChemSpider	2801
UNII	VX4S2N85F5^Y
KEGG	D02061^Y
ChEMBL	CHEMBL1373254
Chemical data
Formula	C₁₃H₁₈ClN₃O₄S₂
Molar mass	379.88 g/mol
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)

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.

CA inhibitors (at PT)	Acetazolamide

Loop (Na-K-Cl at AL)	Furosemide^# Bumetanide Etacrynic acid Etozoline Muzolimine Piretanide Tienilic acid Torasemide

Thiazides (Na-Cl at DCT, Calcium-sparing)	Altizide Bendroflumethiazide Chlorothiazide Cyclopenthiazide Cyclothiazide Epitizide Hydrochlorothiazide^# Hydroflumethiazide Mebutizide Methyclothiazide Polythiazide Trichlormethiazide

Thiazide-likes (primarily DCT)	Quinethazone Clopamide Chlortalidone Mefruside Clofenamide Metolazone Meticrane Xipamide Indapamide Clorexolone Fenquizone

Potassium-sparing (at CD)

ESC blockers	Amiloride^# Triamterene Benzamil

Aldosterone antagonists	Spirolactones: Spironolactone^# Eplerenone Potassium canrenoate Canrenone Non-steroidal: Finerenone

Osmotic diuretics (PT, DL)

Vasopressin receptor inhibitors
(DCT and CD)

Other

Ethanol, Isopropanol, 2M2B
mercurial diuretics (Chlormerodrin, Mersalyl, Meralluride)
Theobromine
Cicletanine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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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Cyclopenthiazide

Synthesis

Contraindications

See also

References