Muzolimine

Muzolimine

File:Muzolimine.png
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Legal status	Withdrawn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 Y
KEGG	D05093 Y
Chemical data
Formula	C11H11Cl2N3O
Molecular 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. It is a pyrazole diuretic which was used for treatment of hypertension but was withdrawn worldwide because of severe neurological side effects.

Synthesis

File:Muzolimine synthesis.svg

Muzolimine synthesis:

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).