Cefroxadine

Cefroxadine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	J01DB11 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	~1 hour
Excretion	Renal
Identifiers
	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;
CAS Number	51762-05-1;
PubChem CID	443991;
ChemSpider	4447587;
UNII	B908C4MV2R;
KEGG	D01528;
ChEMBL	ChEMBL2104150;
CompTox Dashboard (EPA)	DTXSID1022768 ;
ECHA InfoCard	100.052.157
Chemical and physical data
Formula	C16H19N3O5S
Molar mass	365.40 g·mol−1
3D model (JSmol)	Interactive image;
	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.^[1]

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).

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).

References

^ Yasuda K, Kurashige S, Mitsuhashi S (July 1980). "Cefroxadine (CGP-9500), an orally active cephalosporin". Antimicrobial Agents and Chemotherapy. 18 (1): 105–10. doi:10.1128/AAC.18.1.105. PMC 283947. PMID 6998373.
^ [No authors listed]. "Oraspor". Prontuario.it (in Italian). Elsevier. Retrieved 2010-07-31.
^ DE 2331133, Bickel, Hans & Scartazzini, Riccardo, "Enolderivate [Enol derivatives]", published 1974-01-17, assigned to Ciba-Geigy AG
^ R. Scartazzini, H. Bickel, U.S. patent 4,073,902 (1978 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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[1] Yasuda K, Kurashige S, Mitsuhashi S (July 1980). "Cefroxadine (CGP-9500), 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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[2]

[3]

[4]

[5]

Synthesis

See also

References