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Cefroxadine

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Chemical compound Pharmaceutical compound
Cefroxadine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life~1 hour
ExcretionRenal
Identifiers
IUPAC name
  • (6R,7R)-7-{amino}-3-methoxy-8-oxo-5-thia-1-azabicyclooctane-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.052.157 Edit this at Wikidata
Chemical and physical data
FormulaC16H19N3O5S
Molar mass365.40 g·mol
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(/OC)CS12NC(=O)(C/3=C/C\C=C/C\3)N)C(=O)O

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.

It is available in Italy.

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).

Synthesis of cefroxadine

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-diazabicycloundec-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).

See also

References

  1. Yasuda K, Kurashige S, Mitsuhashi S (July 1980). "Cefroxadine (CGP-9000), an orally active cephalosporin". Antimicrobial Agents and Chemotherapy. 18 (1): 105–10. doi:10.1128/AAC.18.1.105. PMC 283947. PMID 6998373.
  2. . "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31.
  3. DE 2331133, Bickel, Hans & Scartazzini, Riccardo, "Enolderivate ", published 1974-01-17, assigned to Ciba-Geigy AG 
  4. R. Scartazzini, H. Bickel, U.S. patent 4,073,902 (1978 to Ciba-Geigy).
  5. R. B. Woodward and H. Bickel, U.S. patent 4,147,864 (1979); Chem. Abstr., 91, 74633J (1979).
Antibacterials active on the cell wall and envelope (J01C-J01D)
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