rosoxacin rosoxacin 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. rosoxacinclinical datatrade nameseradacilahfs/drugs.cominternational drug namesatc codej01mb01 (who) identifiers iupac name 1-ethyl-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid cas number40034-42-2 ypubchem cid287180drugbankdb00817 nchemspider253208 nunii3y1ot3j4nwkeggd02305 nchebichebi:131715 nchemblchembl291157 ncomptox dashboard (epa)dtxsid90193091 echa infocard100.049.763 chemical and physical dataformulac17h14n2o3molar mass294.310 g·mol−13d model (jsmol)interactive imagemelting point290 °c (554 °f) smiles ccn1cc(c(=o)o)c(=o)c2ccc(-c3ccncc3)cc21 inchi inchi=1s/c17h14n2o3/c1-2-19-10-14(17(21)22)16(20)13-4-3-12(9-15(13)19)11-5-7-18-8-6-11/h3-10h,2h2,1h3,(h,21,22) ykey:xbpzxdszhpdxqu-uhfffaoysa-n y ny (what is this?) (verify) it was developed in 1978 by george lesher and his colleagues at winthrop-stearns (now part of sanofi-aventis), as an extension of the work that originally led to nalidixic acid. it is classified as a first generation quinolone. synthesis rosoxacin synthesis: the synthesis of rosoxacin begins with a modified hantzsch pyridine synthesis employing as component parts ammonium acetate, two equivalents of methyl propiolate, and one 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).