Rosoxacin
Antibiotic
- J01MB01 (WHO)
- 1-Ethyl-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid
- 40034-42-2
Y
- 287180
- DB00817
N
- 253208 N
- 3Y1OT3J4NW
- D02305 N
- CHEBI:131715 N
- ChEMBL291157 N
- DTXSID90193091
- Interactive image
- 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)Y
- Key:XBPZXDSZHPDXQU-UHFFFAOYSA-NY
N
Y (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 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.[1][2]
It is classified as a first generation quinolone.[3]
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).
See also
References
- ^ Carabateas PM, Brundage RP, Gelotte KO, Gruett MD, Lorenz RR, Opalka Jr CJ, et al. (1984). "1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. I. Synthesis of 3- and 4-(3-aminophenyl)pyridine intermediates". Journal of Heterocyclic Chemistry. 21 (6): 1849–1856. doi:10.1002/jhet.5570210654.
- ^ Carabateas PM, Brundage RP, Gelotte KO, Gruett MD, Lorenz RR, Opalka Jr CJ, et al. (1984). "1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. II. Synthesis". Journal of Heterocyclic Chemistry. 21 (6): 1857–1863. doi:10.1002/jhet.5570210655.
- ^ 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.
- ^ 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).
- v
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(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
| DHFR inhibitor | |||||||||
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| Sulfonamides (DHPS inhibitor) |
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| Combinations |
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| Other DHPS inhibitors |
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
| 1st generation |
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| Fluoroquinolones |
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| Related (DG) |
inhibitors
| Nitroimidazole derivatives | |
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| Nitrofuran derivatives |
| Rifamycins/ RNA polymerase | |
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| Lipiarmycins |
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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