Cefroxadine
Clinical data | |
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AHFS/Drugs.com | International Drug Names |
Routes of administration | Oral |
ATC code | |
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Pharmacokinetic data | |
Elimination half-life | ~1 hour |
Excretion | Renal |
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Cefroxadine (
INN, trade names Oraspor and Cefthan-DS) is a cephalosporin antibiotic. It is structurally related to cefalexin, and both drugs share a similar spectrum of activity.[1]
It is available in Italy.[2]
Synthesis
Cefroxadine can be prepared by several routes, including one in which the enol is methylated with diazomethane as a key step. A rather more involved route starts with comparatively readily available phenoxymethylpenicillin sulfoxide benzhydryl ester (1).
This undergoes fragmentation when treated with benzothiazole-2-thiol to give 2.
DBU), and the ester protection is removed with trifluoroacetic acid to give 4. The amide side chain is removed by the usual PCl5/dimethylaniline
sequence followed by reamidation with the appropriate acid chloride to give cefroxadine (5).
See also
- Cefachlor
References
- PMID 6998373.
- ^ [No authors listed]. "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31.
- ^ DE 2331133, Bickel, Hans & Scartazzini, Riccardo, "Enolderivate [Enol derivatives]", published 1974-01-17, assigned to Ciba-Geigy AG
- ^ R. Scartazzini, H. Bickel, U.S. patent 4,073,902 (1978 to Ciba-Geigy).
- ^ R. B. Woodward and H. Bickel, U.S. patent 4,147,864 (1979); Chem. Abstr., 91, 74633J (1979).