Rosoxacin

Source: Wikipedia, the free encyclopedia.
Rosoxacin
Clinical data
Trade namesEradacil
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 1-Ethyl-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid
JSmol)
Melting point290 °C (554 °F)
  • CCn1cc(C(=O)O)c(=O)c2ccc(-c3ccncc3)cc21
  • 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) checkY
  • Key:XBPZXDSZHPDXQU-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Rosoxacin (also known as acrosoxacin, tradename Eradacil) is a

sexually transmitted diseases
. Rosoxacin is not available in the United States.

It was developed in 1978 by George Lesher and his colleagues at

sanofi-aventis), as an extension of the work that originally led to nalidixic acid.[1][2]

It is classified as a first generation quinolone.[3]

Synthesis

Rosoxacin synthesis:[4]

The synthesis of rosoxacin begins with a modified

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

  • Fluoroquinolone

References

  1. doi:10.1002/jhet.5570210654
    .
  2. doi:10.1002/jhet.5570210655
    .
  3. PMID 2173670
    .
  4. ^ US 3907808, Lescher Y, Carabateas PM, "1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives", issued 23 September 1975, assigned to STWB Inc. ; Chem. Abstr., 84, 43880p (1975).
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