Cefroxadine

Cefroxadine

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 Number	51762-05-1
ATC code	J01DB11 (WHO)
PubChem	CID: 443991
ChemSpider	4447587
UNII	B908C4MV2R Y
KEGG	D01528
ChEMBL	CHEMBL2104150
Chemical data
Formula	C16H19N3O5S
Molecular mass	365.405 g/mol
SMILES 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.

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 compatively 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-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

• Cefachlor