|Systematic (IUPAC) name|
|AHFS/Drugs.com||International Drug Names|
|Biological half-life||~1 hour|
|ATC code||J01DB11 (WHO)|
|Molar mass||365.405 g/mol|
It is available in Italy.
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 compatively readily available phenoxymethylpenicillin sulfoxide benzhydryl ester (1).
This undergoes fragmentation when treated with benzothiazole-2-thiol to give 2. Ozonolysis (reductive work-up) cleaves the olefinic linkage and the unsymmetrical disulfide moiety is converted to a tosyl thioester (3). The enol moiety is methylated with diazomethane, the six-membered ring is closed by reaction with 1,5-diazabicyclo[5.4.0]undec-5-ene (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).
- Yasuda K, Kurashige S, Mitsuhashi S (July 1980). "Cefroxadine (CGP-9000), an orally active cephalosporin". Antimicrobial Agents and Chemotherapy 18 (1): 105–10. PMC 283947. PMID 6998373.
- [No authors listed]. "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31.
- R. Scartazzini, H. Bickel, DE 2331133 ; eidem, U.S. Patent 4,073,902 (1974, 1978 both to Ciba-Geigy).
- R. B. Woodward and H. Bickel, U.S. Patent 4,147,864 (1979); Chem. Abstr., 91, 74633J (1979).
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