Chemistry:Muzolimine

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Short description: Chemical compound
Muzolimine
Muzolimine.svg
Clinical data
ATC code
Legal status
Legal status
  • Withdrawn
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC11H11Cl2N3O
Molar mass272.13 g·mol−1
3D model (JSmol)
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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is a high-ceiling loop diuretic.[1] It is a pyrazole diuretic which was used for treatment of hypertension but was withdrawn worldwide because of severe neurological side effects.[2]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][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. "The diuretic effect of muzolimine". Pflügers Archiv 410 (6): 674–6. December 1987. doi:10.1007/BF00581331. PMID 3449804. 
  2. "Clinicopharmacological reappraisal of the potency of diuretics". Cardiovascular Drugs and Therapy 7 Suppl 1: 23–8. January 1993. doi:10.1007/BF00877955. PMID 8435374. 
  3. Möller, Eike; Karl Meng & Egbert Wehinger et al., "Diuretisches und antihypertensives Mitel [Diuretic and antihypertensive agent]", DE patent 2319278, published 1974-11-07
  4. E. Möller et al., U.S. Patent 3,957,814 (1976 to Bayer); eidem, Experientia 33, 382 (1977).