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^Y
KEGG	D02061^Y
ChEMBL	CHEMBL1373254
ECHA InfoCard	100.010.920
Chemical and physical data
Formula	C₁₃H₁₈ClN₃O₄S₂
Molar mass	379.88 g/mol
3D model (Jmol)	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
(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.

Symporter inhibitors

Na⁺-Cl⁻	Thiazides: Bendroflumethiazide Chlorothiazide Cyclopenthiazide Cyclothiazide Hydrochlorothiazide Hydroflumethiazide Methyclothiazide Polythiazide Trichlormethiazide; Others: Chlortalidone (chlorthalidone) Metolazone

Na⁺-K⁺-Cl⁻	Bumetanide Furosemide

Antihypertensives: diuretics (C03)

Sulfonamides
(and etacrynic acid)

CA inhibitors (at PT)	Acetazolamide

Loop (Na-K-Cl at AL)	Furosemide^# Bumetanide Etacrynic acid Etozolin Muzolimine Ozolinone 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