Structure via PubChem · Public domain (PubChem)
(E)-cefprozil
Sign in to saveAlso known as (E)-cefprozil anhydrous, cefprozil anhydrous
Cefprozil is a second-generation cephalosporin antibiotic. Originally discovered in 1983, and approved in 1992, it was sold under the tradename Cefzil by Bristol Meyers Squibb until 2010 when the brand name version was discontinued. It continues to be available from various companies in its generic form. It is used in the treatment of pharyngitis, tonsillitis, ear infections, acute sinusitis, bacterial exacerbation of chronic bronchitis, and skin and skin structure infections. It is currently available as a tablet and as a liquid suspension.
Chemical data
- Formula
- C18H19N3O5S
- Molecular weight
- 389.4 g/mol
- IUPAC name
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(E)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- C/C=C/C1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O
- InChIKey
- WDLWHQDACQUCJR-ZAMMOSSLSA-N
- XLogP
- -1.4
- Polar surface area
- 158 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
1 papers- The stability of cefprozil in oral suspension CEFZIL.Acta poloniae pharmaceutica · 2008
via PubMed
Wikidata facts
- Mass
- 389.104542
Show 4 more facts
- chemical formula
- C₁₈H₁₉N₃O₅S
- isomeric SMILES
- C/C=C/C1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O
- canonical SMILES
- CC=CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O
- defined daily dose
- 1.0
via Wikidata · CC0
~2 min read
Article
5 sectionsContents
- Adverse effects
- Spectrum of bacterial susceptibility and resistance
- Synthesis
- References
- External links
Cefprozil is a second-generation cephalosporin antibiotic. Originally discovered in 1983, and approved in 1992, it was sold under the tradename Cefzil by Bristol Meyers Squibb until 2010 when the brand name version was discontinued. It continues to be available from various companies in its generic form. It is used in the treatment of pharyngitis, tonsillitis, ear infections, acute sinusitis, bacterial exacerbation of chronic bronchitis, and skin and skin structure infections. 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. 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.