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Cefprozil

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Cefprozil
Clinical data
Trade namesCefzil
AHFS/Drugs.comMonograph
MedlinePlusa698022
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability95%
Protein binding36%
Elimination half-life1.3 hours
Identifiers
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H19N3O5S
Molar mass389.427 g/mol g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:ALYUMNAHLSSTOU-HERYOFLYSA-N checkY
 ☒NcheckY (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.[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 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).
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