A cephalosporin antibiotic
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Labeled Version(s)
33639Cefprozil-d4
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Cefprozil

Item No. 23840

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(1-propen-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
92665-29-7
Synonyms
  • BMY-28100
Molecular Formula
C18H19N3O5S
Formula Weight
389.4
Purity
≥95% (mixture of cis and trans)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.3 mg/mlDMSO: 2.5 mg/mlPBS (pH 7.2): 1.25 mg/ml
λmax
232, 283 nm
SMILES
O=C(O)C1=C(/C=C/C)CS[C@@]([C@@H]2NC([C@H](N)C3=CC=C(O)C=C3)=O)([H])N1C2=O
InChi Code
InChI=1S/C18H19N3O5S/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)/b3-2+/t12-,13-,17-/m1/s1
InChi Key
WDLWHQDACQUCJR-ZAMMOSSLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Cefprozil is an orally bioavailable, second generation, broad-spectrum cephalosporin antibiotic that inhibits the growth of both Gram-positive and Gram-negative bacteria.1,2 It inhibits the growth of E. coli, E. faecalis, E. faecium, N. gonorrhoeae, N. meningitidis, P. mirabilis, S. aureus, S. pyogenes, and S. pneumoniae strains (MICs = 0.013-25 μg/ml) and clinical isolates of penicillin-susceptible, -intermediate, and -resistant S. pneumoniae and methicillin-sensitive S. aureus (MIC90s = 0.12-16 μg/ml). In vivo, cefprozil protects mice challenged with E. coli, S. aureus, S. pyogenes, and P. mirabilis strains with protective doses (PD50s) ranging from 0.07 to 1.3 mg/kg.1 Cefprozil binds to penicillin-binding proteins (PBPs), which disrupts their ability to cross-link peptidoglycan and leads to weakened bacterial cell walls.3 Formulations containing cefprozil have been used in the treatment of respiratory tract, skin, and other bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tomatsu, K., Ando, S., Masuyoshi, S., et al. In vitro and in vivo evaluations of BMY-28100, a new oral cephalosporin. J. Antibiot. (Tokyo) 40(8), 1175-1183 (1987).

    2. Peric, M., Browne, F.A., Jacobs, M.R., et al. Activity of nine oral agents against gram-positive and gram-negative bacteria encountered in community-acquired infections: Use of pharmacokinetic/pharmacodynamic breakpoints in the comparative assessment of beta-lactam and macrolide antimicrobial agents. Clin. Ther. 25(1), 169-177 (2003).

    3. Nagai, K., Davies, T.A., Jacobs, M.R., et al. Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob. Agents Chemother. 46(5), 1273-1280 (2002).