Kalpana Kalpana (Editor)

Rosoxacin

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ATC code
  
J01MB01 (WHO)

PubChem CID
  
287180

ChemSpider
  
253208

CAS Number
  
40034-42-2

DrugBank
  
DB00817

Molar mass
  
294.3 g/mol

Rosoxacin

AHFS/Drugs.com
  
International Drug Names

Rosoxacin (also known as acrosoxacin, tradename Eradacil) is a quinolone antibiotic indicated for the treatment of urinary tract infections and certain sexually transmitted diseases. Rosoxacin is not available in the United States.

It was developed by Sanofi-Synthelabo (now part of sanofi-aventis).

It is classified as first generation.

Synthesis

The synthesis of rosoxacin begins with a modified Hantzsch pyridine synthesis employing as component parts ammonium acetate, two equivalents of methyl propiolate, and 1 of 3-nitrobenzaldehyde. Oxidation of the resulting dihydropyridine (2) with nitric acid followed by saponification, decarboxylation, and reduction of the nitro group with iron and HCl acid gives aniline 3. This undergoes the classic sequence of Gould-Jacobs reaction with methoxymethylenemalonate ester to form the 4-hydroxyquinoline ring, and then alkylation with ethyl iodide and saponification of the ester to complete the synthesis of the antibacterial agent rosoxacin (4).

References

Rosoxacin Wikipedia