Cefprozil

Cefprozil
Clinical data
Trade names Cefzil
AHFS/Drugs.com Monograph
MedlinePlus a698022
License data
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration		 Oral
ATC code J01DC10 (WHO)
Legal status
Legal status
Pharmacokinetic data
Bioavailability 95%
Protein binding 36%
Biological half-life 1.3 hours
Identifiers
CAS Number 92665-29-7 YesY
PubChem (CID) 9887643
DrugBank DB01150 YesY
ChemSpider 8063315 YesY
UNII 1M698F4H4E YesY
KEGG D07651 YesY
ChEBI CHEBI:3506 N
ChEMBL CHEMBL1742 N
ECHA InfoCard 100.110.585
Chemical and physical data
Formula C18H19N3O5S
Molar mass 389.427 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

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 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

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. 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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