Chemical compound
Pharmaceutical compound
Cefprozil Trade names Cefzil, Cefproz, others Other names Cefproxil AHFS /Drugs.com Monograph MedlinePlus a698022 License data
Routes of administration Oral ATC code Legal status
Bioavailability 95% Protein binding 36% Elimination half-life 1.3 hours
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 ) Formula C 18 H 19 N 3 O 5 S 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
Y Key:ALYUMNAHLSSTOU-HERYOFLYSA-N
Y
N Y (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 .
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:[ 8] [ 9] [ 10] Separation of isomers:[ 11]
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
^ "Cefzil (cefprozil) dosing, indications, interactions, adverse effects, and more" . reference.medscape.com . Retrieved 2021-05-12 .
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery . John Wiley & Sons. p. 496. ISBN 9783527607495 .
^ "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.
^ "Drugs@FDA: FDA-Approved Drugs" . www.accessdata.fda.gov . Retrieved 2022-08-03 .
^ a b "Cefzil® (CEFPROZIL) Prescribing Facts" (PDF) . U.S. Food and Drug Administration . Bristol Myers Squibb.
^ 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 .
^ "Cefprozil Susceptibility and Resistance Data" (PDF) . Retrieved 23 July 2013 .
^ 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 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 .
^ 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 .
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