Cefprozil

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.

Cefprozil

Clinical data
Trade names	Cefzil, Cefproz, others
Other names	Cefproxil
AHFS/Drugs.com	Monograph
MedlinePlus	a698022
License data	US FDA: Cefprozil
Routes of administration	Oral
ATC code	J01DC10 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	95%
Protein binding	36%
Elimination half-life	1.3 hours
Identifiers
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
CAS Number	92665-29-7 Y
PubChem CID	9887643
DrugBank	DB01150 Y
ChemSpider	8063315 Y
UNII	1M698F4H4E
KEGG	D07651 Y
ChEBI	CHEBI:3506 N
ChEMBL	ChEMBL1742 N
CompTox Dashboard (EPA)	DTXSID10873545
Chemical and physical data
Formula	C18H19N3O5S
Molar mass	389.43 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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
NY (what is this?)  (verify)

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]