Muzolimine

Muzolimine

Systematic (IUPAC) name
5-amino-2-[1-(3,4-dichlorophenyl)ethyl]-4H-pyrazol-3-one
Clinical data
Legal status	Withdrawn
Identifiers
ATC code	C03CD01 (WHO)
PubChem	CID 41386
ChemSpider	37766
UNII	07Z36289ZX
KEGG	D05093
Chemical data
Formula	C11H11Cl2N3O
Molar mass	272.13 g/mol
SMILES CC(C1=CC(=C(C=C1)Cl)Cl)N2C(=O)CC(=N2)N
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is a High-ceiling loop diuretic.^[1] It is a pyrazole diuretic which was used for treatment of hypertension but was withdrawn worldwide because of severe neurological side effects.^[2]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

1. Wangemann, P.; Braitsch, R.; Greger, R. (1987). "The diuretic effect of muzolimine". Pflugers Archiv : European journal of physiology 410 (6): 674–676. PMID 3449804.
2. Reyes, A. J.; Leary, W. P. (1993). "Clinicopharmacological reappraisal of the potency of diuretics". Cardiovascular Drugs and Therapy 7: 23–28. 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).