Cefprozil

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Cefprozil
File:Cefprozil.svg
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
Licence data US FDA:link
Pregnancy
category
  • US: B (No risk in non-human studies)
Legal status
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability 95%
Protein binding 36%
Biological half-life 1.3 hours
Identifiers
CAS Number 92665-29-7 YesY
ATC code J01DC10 (WHO)
PubChem CID: 9887643
DrugBank DB01150 YesY
ChemSpider 8063315 YesY
UNII 1M698F4H4E YesY
KEGG D07651 YesY
ChEBI CHEBI:3506 N
ChEMBL CHEMBL1742 N
Chemical data
Formula C18H19N3O5S
Molecular mass 389.427 g/mol
  • 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 YesY
  • Key:ALYUMNAHLSSTOU-HERYOFLYSA-N YesY
 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.[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

File:Cefprozil synthesis.svg
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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ H. Hoshi et al., DE 3402642 ; eidem, U.S. Patent 4,520,022 (1984, 1985 both to Bristol-Myers).
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ M. A. Kaplan et al., U.S. Patent 4,727,070 (1988 to Bristol-Myers).

External links

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