Movatterモバイル変換

[0]ホーム

Jump to content

Muzolimine

Edit links

From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Muzolimine
Clinical data

ATC code	C03CD01 (WHO)
Legal status
Legal status	Withdrawn
Identifiers
IUPAC name 5-amino-2-[1-(3,4-dichlorophenyl)ethyl]-4H-pyrazol-3-one
CAS Number	55294-15-0^N
PubChemCID	41386
ChemSpider	37766^N
UNII	07Z36289ZX
KEGG	D05093^Y
CompTox Dashboard(EPA)	DTXSID50866476
ECHA InfoCard	100.054.139
Chemical and physical data
Formula	C₁₁H₁₁Cl₂N₃O
Molar mass	272.13 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1CC(N)=NN1C(C)c2cc(Cl)c(Cl)cc2
InChI InChI=1S/C11H11Cl2N3O/c1-6(16-11(17)5-10(14)15-16)7-2-3-8(12)9(13)4-7/h2-4,6H,5H2,1H3,(H2,14,15)^N Key:RLWRMIYXDPXIEX-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Muzolimine is a high-ceilingloop diuretic.^[1] It is apyrazole diuretic which was used for treatment ofhypertension but was withdrawn worldwide because of severe neurological side effects.^[2]

Synthesis

[edit]

Rxn of (1-(3,4-dichlorophenyl)ethyl)hydrazine (1) with ethyl 3-amino-3-ethoxyacrylate (2) leads to a ring-forming two-site reaction and formation of the pyrazoline diuretic agent, muzolimine (3).

References

[edit]

^Wangemann P, Braitsch R, Greger R (December 1987). "The diuretic effect of muzolimine".Pflügers Archiv.410 (6):674–6.doi:10.1007/BF00581331.PMID 3449804.S2CID 19367481.
^Reyes AJ, Leary WP (January 1993). "Clinicopharmacological reappraisal of the potency of diuretics".Cardiovascular Drugs and Therapy. 7 Suppl 1:23–8.doi:10.1007/BF00877955.PMID 8435374.S2CID 29589710.
^DE 2319278, Möller, Eike; Meng, Karl & Wehinger, Egbert et al., "Diuretisches und antihypertensives Mitel [Diuretic and antihypertensive agent]", published 1974-11-07, assigned toBayer AG
^E. Möller et al.,U.S. patent 3,957,814 (1976 to Bayer); eidem, Experientia 33, 382 (1977).

Diuretics (C03)

Sulfonamides
(andetacrynic acid)

CA inhibitors (atPT)	Acetazolamide
Loop (Na-K-Cl atAL)	Furosemide^# Azosemide Bumetanide Etacrynic acid Etozolin Indacrinone Muzolimine Ozolinone Piretanide Tienilic acid^‡ Torasemide
Thiazides (Na-Cl atDCT, Calcium-sparing)	Altizide Bendroflumethiazide Butizide Chlorothiazide Cyclopenthiazide Cyclothiazide Epitizide Hydrochlorothiazide Hydroflumethiazide Mebutizide Methyclothiazide Polythiazide Trichlormethiazide
Thiazide-likes (primarilyDCT)	Chlortalidone Clofenamide Clopamide Clorexolone Fenquizone Indapamide (+telmisartan and amlodipine) Mefruside Meticrane Metolazone Quinethazone Xipamide

Potassium-sparing (atCD)

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