Rosoxacin

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Rosoxacin
Rosoxacin.svg
Systematic (IUPAC) name
1-Ethyl-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Registry Number 40034-42-2 YesY
ATC code J01MB01
PubChem CID: 287180
DrugBank DB00817 N
ChemSpider 253208 N
UNII 3Y1OT3J4NW N
KEGG D02305 N
ChEMBL CHEMBL291157 N
Chemical data
Formula C17H14N2O3
Molecular mass 294.30 g/mol
Physical data
Melting point 290 °C (554 °F)
 N (what is this?)  (verify)

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.[1]

Synthesis[edit]

Rosoxacin synthesis:[2]

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).

See also[edit]

References[edit]

  1. ^ Przybilla B, Georgii A, Bergner T, Ring J (1990). "Demonstration of quinolone phototoxicity in vitro". Dermatologica 181 (2): 98–103. doi:10.1159/000247894. PMID 2173670. 
  2. ^ Y.Lescher and P. M. Carabateas, U.S. Patent 3,907,808 (1975); Chem. Abstr., 84, 43880p (1975).