Cefprozil

Last updated
Cefprozil
Cefprozil.svg
Clinical data
Trade names Cefzil, Cefproz, others
Other namesCefproxil
AHFS/Drugs.com Monograph
MedlinePlus a698022
License data
Routes of
administration 		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 95%
Protein binding 36%
Elimination half-life 1.3 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
Formula C18H19N3O5S
Molar mass 389.43 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 Yes check.svgY
  • Key:ALYUMNAHLSSTOU-HERYOFLYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Cefprozil is a second-generation cephalosporin antibiotic. [1] Originally discovered in 1983, and approved in 1992, [2] it was sold under the tradename Cefzil by Bristol Meyers Squibb until 2010 when the brand name version was discontinued. [3] It continues to be available from various companies in its generic form. [4] It is used in the treatment of pharyngitis, tonsillitis, ear infections, acute sinusitis, bacterial exacerbation of chronic bronchitis, and skin and skin structure infections. [5] It is currently available as a tablet and as a liquid suspension.

Contents

Adverse effects

Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, research has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins. [6] The most common side effects were increased hepatic lab values (including AST and ALGT), dizziness, eosinophilia, diaper rash and superinfection, genital pruritus, vaginitis, diarrhea, nausea, vomiting, and abdominal pain. [5]

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. [7]

Synthesis

Cefprozil synthesis: Separation of isomers: Cefprozil synthesis.svg
Cefprozil synthesis: Separation of isomers:

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. [12] [13]

References

  1. ↑ "Cefzil (cefprozil) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Retrieved 2021-05-12.
  2. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN   9783527607495.
  3. ↑ "Determination That CEFZIL (Cefprozil) Tablets, 250 Milligrams and 500 Milligrams, and for Oral Suspension, 125 Milligrams/5 Milliliters and 250 Milligrams/5 Milliliters, Were Not Withdrawn From Sale for Reasons of Safety or Effectiveness". The Federal Register. National Archives. 11 September 2018.
  4. ↑ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 2022-08-03.
  5. 1 2 "Cefzil® (CEFPROZIL) Prescribing Facts" (PDF). U.S. Food and Drug Administration. Bristol Myers Squibb.
  6. ↑ Pichichero ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of Family Practice. 55 (2): 106–112. PMID   16451776. Archived from the original on 2012-09-16. Retrieved 2011-02-26.
  7. ↑ "Cefprozil Susceptibility and Resistance Data" (PDF). Retrieved 23 July 2013.
  8. ↑ DE 3402642,Hoshi H, et al.,issued 1984, assigned to Bristol-Myers
  9. ↑ US 4520022,Hoshi H, et al.,issued 1985, assigned to Bristol-Myers
  10. ↑ Naito T, Hoshi H, Aburaki S, Abe Y, Okumura J, Tomatsu K, Kawaguchi H (July 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.
  11. ↑ US 4727070,Kaplan MA, et al.,issued 1988, assigned to Bristol-Myers
  12. ↑ Tomatsu K, Ando S, Masuyoshi S, Kondo S, Hirano M, Miyaki T, Kawaguchi H (August 1987). "In vitro and in vivo evaluations of BMY-28100, a new oral cephalosporin". The Journal of Antibiotics. 40 (8): 1175–1183. doi: 10.7164/antibiotics.40.1175 . PMID   3500158.
  13. ↑ Albanus L, Björklund NE, Gustafsson B, Jönsson M (1975). "Forty days oral toxicity of 2,6-cis-diphenylhexamethylcyclotetrasiloxane (KABI 1774)in beagle dogs with special reference to effects on the male reproductive system". Acta Pharmacologica et Toxicologica. 36 (Suppl 3): 93–130. doi:10.1111/j.1600-0773.1975.tb03087.x. PMID   1080338.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.