Cyclopenthiazide

Chemical compound

C03AA07 (WHO)

Legal statusLegal 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^Y

ChEMBL

ChEMBL1373254

CompTox Dashboard (EPA)

DTXSID4022868

ECHA InfoCard100.010.920

Chemical and physical dataFormulaC₁₃H₁₈ClN₃O₄S₂Molar mass379.87 g·mol⁻¹3D 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

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^# Azosemide Bumetanide Etacrynic acid Etozolin Indacrinone Muzolimine Ozolinone Piretanide Tienilic acid^‡ Torasemide
Thiazides (Na-Cl at DCT, Calcium-sparing)	Altizide Bendroflumethiazide Butizide Chlorothiazide Cyclopenthiazide Cyclothiazide Epitizide Hydrochlorothiazide Hydroflumethiazide Mebutizide Methyclothiazide Polythiazide Trichlormethiazide
Thiazide-likes (primarily DCT)	Chlortalidone Clofenamide Clopamide Clorexolone Fenquizone Indapamide Mefruside Meticrane Metolazone Quinethazone Xipamide

Potassium-sparing (at CD)

ESC blockers	Amiloride^# Benzamil Triamterene
Aldosterone antagonists	Spirolactones Spironolactone^# Canrenone Eplerenone Potassium canrenoate Nonsteroidal Finerenone

Osmotic diuretics (PT, DL)

Vasopressin receptor inhibitors
(DCT and CD)

Vaptans

Others
- Demeclocycline
- Lithium carbonate

Other

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

Combination products

Hydrochlorothiazide/triamterene

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^‡Withdrawn from market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

References

^ 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.