Muzolimine

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Legal status	Withdrawn;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 ;
PubChem CID	41386;
ChemSpider	37766 ;
UNII	07Z36289ZX;
KEGG	D05093 ;
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) ; Key:RLWRMIYXDPXIEX-UHFFFAOYSA-N ;
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Muzolimine is a High-ceiling loop diuretic.[1] It is a pyrazole diuretic which was used for treatment of hypertension but was withdrawn worldwide because of severe neurological side effects.[2]

Synthesis

Muzolimine synthesis:[3]

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

Wangemann P, Braitsch R, Greger R (December 1987). "The diuretic effect of muzolimine". Pflugers Archiv. 410 (6): 674–6. doi:10.1007/BF00581331. PMID 3449804.
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.
E. Möller et al., DE 2319278; eidem, U.S. Patent 3,957,814 (1974, 1976 both to Bayer); eidem, Experientia 33, 382 (1977).

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[1] Wangemann P, Braitsch R, Greger R (December 1987). "The diuretic effect of muzolimine". Pflugers Archiv. 410 (6): 674–6. doi:10.1007/BF00581331. PMID 3449804.

[2] 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.

[3] E. Möller et al., DE 2319278; eidem, U.S. Patent 3,957,814 (1974, 1976 both to Bayer); eidem, Experientia 33, 382 (1977).