Cefprozil

Cefprozil

Systematic (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
Clinical data
Trade names	Cefzil
AHFS/Drugs.com	monograph
MedlinePlus	a698022
License data	US FDA: Cefprozil
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Oral
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	95%
Protein binding	36%
Biological half-life	1.3 hours
Identifiers
CAS Number	92665-29-7
ATC code	J01DC10 (WHO)
PubChem	CID 9887643
DrugBank	DB01150
ChemSpider	8063315
UNII	1M698F4H4E
KEGG	D07651
ChEBI	CHEBI:3506
ChEMBL	CHEMBL1742
Chemical data
Formula	C18H19N3O5S
Molar mass	389.427 g/mol
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. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections. 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 Agona and Streptococci are susceptible to Cefprozil. Some of the bacteria like Brucella abortus, Moraxella catarrhalis and Streptococcus pneumonia have developed resistance towards Cefprozil in varying degrees. For detailed minimum inhibition concentration information, please refer to Cefprozil Susceptibility and Resistance Data sheet.^[2]

Synthesis

Cefprozil synthesis:^[3][4] Separation of isomers:^[5]

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

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. PMID 3624077.
5. M. A. Kaplan et al., U.S. Patent 4,727,070 (1988 to Bristol-Myers).

External links

• Cefprozil MedlinePlus Drug Information