Muzolimine

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is a High-ceiling loop diuretic.[1] It is a pyrazole diuretic which was used for treatment of hypertension but was withdrawn worldwide because of severe neurological side effects.[2]

Muzolimine
Clinical data
ATC code
Legal status
Legal status
  • Withdrawn
Identifiers
IUPAC name
  • 5-amino-2-[1-(3,4-dichlorophenyl)ethyl]-4H-pyrazol-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.054.139
Chemical and physical data
FormulaC11H11Cl2N3O
Molar mass272.13 g·mol−1
3D model (JSmol)
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)

Synthesis
Muzolimine synthesis:[3][4]

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 (December 1987). "The diuretic effect of muzolimine". Pflügers 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. DE 2319278, Möller, Eike; Meng, Karl & Wehinger, Egbert et al., "Diuretisches und antihypertensives Mitel [Diuretic and antihypertensive agent]", published 1974-11-07, assigned to Bayer AG
  4. E. Möller et al., U.S. Patent 3,957,814 (1976 to Bayer); eidem, Experientia 33, 382 (1977).


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