Cefprozil is a second-generation

cephalosporin The cephalosporins (sg. ) are a class of β-lactam antibiotics originally derived from the fungus ''Acremonium'', which was previously known as ''Cephalosporium''. Together with cephamycins, they constitute a subgroup of β-lactam antibiotics ...

antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

. Originally discovered in 1983, and approved in 1992, it was sold under the tradename Cefzil by

Bristol Meyers Squibb The Bristol Myers Squibb Company (BMS) is an American multinational pharmaceutical company. Headquartered in New York City, BMS is one of the world's largest pharmaceutical companies and consistently ranks on the ''Fortune'' 500 list of the lar ...

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 Otitis is a general term for inflammation or infection, inner ear infection, middle ear infection of the ear, in both humans and other animals. When infection is present, it may be viral or bacterial. When inflammation is present due to fluid bui ...

acute sinusitis Sinusitis, also known as rhinosinusitis, is inflammation of the mucous membranes that line the sinuses resulting in symptoms that may include thick nasal mucus, a plugged nose, and facial pain. Other signs and symptoms may include fever, headac ...

, bacterial exacerbation of chronic bronchitis, and

skin and skin structure infection Skin and skin structure infections (SSSIs), also referred to as skin and soft tissue infections (SSTIs), or acute bacterial skin and skin structure infections (ABSSSIs), are infections of skin and associated soft tissues (such as loose connective ti ...

s. 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.

Spectrum of bacterial susceptibility and resistance

Currently, bacteria like '' Enterobacter aerogenes'', ''

Morganella morganii ''Morganella morganii'' is a species of Gram-negative bacteria.eMedicineMorganella infections/ref> It has a commensal relationship within the intestinal tracts of humans, mammals, and reptiles as normal flora. Although ''M. morganii'' has a wide ...

'' and '' Pseudomonas aeruginosa'' are resistant to cefprozil, while '' Salmonella enterica'' serotype Agona and

streptococci ''Streptococcus'' is a genus of gram-positive ' (plural ) or spherical bacteria that belongs to the family Streptococcaceae, within the order Lactobacillales (lactic acid bacteria), in the phylum Bacillota. Cell division in streptococci occurs ...

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.

Synthesis

This is not a direct copy of Lednicer book like at first glance, but is sourced from the primary reference material. Cefprozil synthesis

Displacement of the allylic chloride in intermediate (1) with triphenylphosphine gives the phosphonium salt (2). This functionality is then converted to its

ylide An ylide or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms h ...

; condensation with

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...

then leads to the vinyl derivative (3); deprotection then gives cefprozil. Semisynthetic oral cephalosporin consisting of ~90:10 Z/E isomeric mixture.

References

External links

Cefprozil
MedlinePlus Drug Information Cephalosporin antibiotics Phenols {{antibiotic-stub