Cefroxadine

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Cefroxadine
Cefroxadine.svg
Systematic (IUPAC) name
(6R,7R)-7-{[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino}-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • (Prescription only)
Routes of
administration
Oral
Pharmacokinetic data
Biological half-life ~1 hour
Excretion Renal
Identifiers
CAS Registry Number 51762-05-1
ATC code J01DB11
PubChem CID: 443991
ChemSpider 4447587
UNII B908C4MV2R YesY
KEGG D01528
ChEMBL CHEMBL2104150
Chemical data
Formula C16H19N3O5S
Molecular mass 365.405 g/mol

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[edit]

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).

Orally active cephalosporin deriv. Prepn:[3][4]

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. The result of all this is cefroxadine (5).

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ [No authors listed]. "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31. 
  3. ^ R. Scartazzini, H. Bickel, DE 2331133 ; eidem, U.S. Patent 4,073,902 (1974, 1978 both to Ciba-Geigy).
  4. ^ R. B. Woodward and H. Bickel, U.S. Patent 4,147,864 (1979); Chem. Abstr., 91, 74633J (1979).