Cefprozil

Cefprozil
Clinical data
Trade names	Cefzil
AHFS/Drugs.com	Monograph
MedlinePlus	a698022
License data	US FDA: Cefprozil;
Routes of; administration	Oral
ATC code	J01DC10 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	95%
Protein binding	36%
Elimination half-life	1.3 hours
Identifiers
	IUPAC name 7-[2-amino-2-(4-hydroxyphenyl)-acetyl]amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	92665-29-7 ;
PubChem CID	9887643;
DrugBank	DB01150 ;
ChemSpider	8063315 ;
UNII	1M698F4H4E;
KEGG	D07651 ;
ChEBI	CHEBI:3506 ;
ChEMBL	ChEMBL1742 ;
CompTox Dashboard (EPA)	DTXSID10873545 ;
Chemical and physical data
Formula	C18H19N3O5S
Molar mass	389.427 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(/C=C/C)CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccc(O)cc3)N)C(=O)O.O;
	InChI InChI=1S/C18H19N3O5S.H2O/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9;/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26);1H2/b3-2-;/t12-,13-,17-;/m1./s1 ; Key:ALYUMNAHLSSTOU-HERYOFLYSA-N ;
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Cefprozil, sometimes spelled cefproxil and marketed under the trade name Cefzil,Cefproz.

Cefprozil is a second-generation cephalosporin type antibiotic. In Europe it is marketed using the trade names Procef and Cronocef.^{[citation needed]} It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.^{[citation needed]} It comes as a tablet and as a liquid suspension.

Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, an article in the Journal of Family Practice^[1] has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins.

Spectrum of bacterial susceptibility and resistance

Currently bacteria like Enterobacter aerogenes, Morganella morganii and Pseudomonas aeruginosa are resistant to cefprozil, while Salmonella enterica serotype Agona and streptococci are susceptible to cefprozil. Some bacteria like Brucella abortus, Moraxella catarrhalis and Streptococcus pneumoniae have developed resistance towards cefprozil in varying degrees. Detailed minimum inhibition concentration information is given by the Cefprozil Susceptibility and Resistance Data sheet.^[2]

Synthesis

Displacement of the allylic chloride in intermediate (1) with triphenylphosphine gives the phosphonium salt (2). This functionality is then converted to its ylide; condensation with acetaldehyde then leads to the vinyl derivative (3); deprotection then gives cefprozil. Semisynthetic oral cephalosporin consisting of ~90:10 Z/E isomeric mixture.

References

^ Pichichero, ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients". J Fam Pract. 55 (2): 106–12. PMID 16451776.
^ "Cefprozil Susceptibility and Resistance Data" (PDF). Retrieved 23 July 2013.
^ H. Hoshi et al., DE 3402642 ; eidem, U.S. patent 4,520,022 (1984, 1985 both to Bristol-Myers).
^ Naito, T; Hoshi, H; Aburaki, S; Abe, Y; Okumura, J; Tomatsu, K; Kawaguchi, H (1987). "Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds". The Journal of antibiotics. 40 (7): 991–1005. doi:10.7164/antibiotics.40.991. PMID 3624077.
^ M. A. Kaplan et al., U.S. patent 4,727,070 (1988 to Bristol-Myers).

External links

Cefprozil MedlinePlus Drug Information

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[1] Pichichero, ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients". J Fam Pract. 55 (2): 106–12. PMID 16451776.

[2] "Cefprozil Susceptibility and Resistance Data" (PDF). Retrieved 23 July 2013.

[3] H. Hoshi et al., DE 3402642 ; eidem, U.S. patent 4,520,022 (1984, 1985 both to Bristol-Myers).

[4] Naito, T; Hoshi, H; Aburaki, S; Abe, Y; Okumura, J; Tomatsu, K; Kawaguchi, H (1987). "Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds". The Journal of antibiotics. 40 (7): 991–1005. doi:10.7164/antibiotics.40.991. PMID 3624077.

[5] M. A. Kaplan et al., U.S. patent 4,727,070 (1988 to Bristol-Myers).

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