|Trade names||Cefzil, Cefproz, others|
|Other names||Cephprozil, cefproxil|
|Drug class||Antibiotic (2nd-generation cephalosporin)|
|Main uses||Middle ear infections, skin infections, strep throat, pneumonia|
|Side effects||Diarrhea, nausea, liver problems, rash, dizziness, vaginal yeast infections|
|Elimination half-life||1.3 hours|
|Chemical and physical data|
|Molar mass||389.43 g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Common side effects include diarrhea, nausea, liver problems, rash, dizziness, and vaginal yeast infections. Other side effects may include allergic reactions and Clostridioides difficile infection. While there is no evidence of harm in pregnancy, such use has not been well studied. It is in the second-generation cephalosporin family of medications.
Spectrum of activity
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.
In adults it is typically take at a dose of 250 to 500 mg twice per day.
Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, an article has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins.
This is not a direct copy of Lednicer book like at first glance, but is sourced from the primary reference material.
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.
- Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 832. ISBN 978-1-260-45231-0.
- "Cefprozil Monograph for Professionals". Drugs.com. Retrieved 30 December 2021.
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- "Cefprozil". Retrieved 30 December 2021.
- "Cefprozil Susceptibility and Resistance Data" (PDF). Retrieved 23 July 2013.
- Pichichero ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of Family Practice. 55 (2): 106–12. PMID 16451776. Archived from the original on 2012-09-16. Retrieved 2011-02-26.
- DE 3402642, Hoshi H, et al., issued 1984, assigned to Bristol-Myers
- US 4520022, Hoshi H, et al., issued 1985, assigned to Bristol-Myers
- 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.
- US 4727070, Kaplan MA, et al., issued 1988, assigned to Bristol-Myers
- TOMATSU, Kozo; Ando, Shigeyuki; Masuyoshi, Shinji; Kondo, Shoichiro; Hirano, Minoru; Miyaki, Takeo; Kawaguchi, Hiroshi (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. ISSN 0021-8820. PMID 3500158.
- Cefprozil MedlinePlus Drug Information