Cefroxadine

Last updated
Cefroxadine
Cefroxadine.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life ~1 hour
Excretion Renal
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.052.157 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H19N3O5S
Molar mass 365.40 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(/OC)CS[C@@H]1[C@@H]2NC(=O)[C@@H](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. [1]

Contents

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).

Synthesis of cefroxadine Cefroxadine synthesis.svg
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-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).

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. ↑ [No authors listed]. "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31.
  3. ↑ DE 2331133,Bickel, Hans&Scartazzini, Riccardo,"Enolderivate [Enol derivatives]",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).
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