Cefprozil

• CAT Number: R007816
• CAS Number: 92665-29-7
• Molecular Formula: C18H19N3O5S
• Purity: ≥95%
• Storage: Store at -20°C
• InChI: 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
• InChIKey: WDLWHQDACQUCJR-ZAMMOSSLSA-N
• 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

Cefprozil, under the marketed trade name Cefzil, is a second-generation cephalosporin type antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections. It comes as a tablet and as a liquid suspension. Cefprozil/’s effect is dependent on its binding to penicillin-binding proteins (PBPs) located in the bacterial cytoplasmic membrane. Binding results in the inhibition of the transpeptidase enzymes, thereby preventing cross-linking of the pentaglycine bridge with the fourth residue of the pentapeptide and interrupting consequent synthesis of peptidoglycan chains. As a result, cefprozil inhibits bacterial septum and cell wall synthesis formation.

Reference

1:Molecular and Quantum Mechanical Study for the Separation of Cefprozil in the Presence of Its Alkaline Degradation Product Using RP-HPLC with UV Detection. Attia KA, Nassar MW, El-Zeiny MB, Serag A.J AOAC Int. 2017 Mar 1;100(2):392-399. doi: 10.5740/jaoacint.16-0246. Epub 2016 Nov 17. PMID: 28118569 2:Effects of quercetin on pharmacokinetics of cefprozil in Chinese-Han male volunteers. Jia FF, Tan ZR, McLeod HL, Chen Y, Ou-Yang DS, Zhou HH.Xenobiotica. 2016 Oct;46(10):896-900. doi: 10.3109/00498254.2015.1132792. Epub 2016 Feb 29. PMID: 26928207 3:Stability indicating methods for the analysis of cefprozil in the presence of its alkaline induced degradation product. Attia KA, Nassar MW, El-Zeiny MB, Serag A.Spectrochim Acta A Mol Biomol Spectrosc. 2016 Apr 15;159:1-6. doi: 10.1016/j.saa.2016.01.026. Epub 2016 Jan 21. PMID: 26814624 4:In Vitro Activity of Oral Cephalosporins (Cefprozil and Cefixime) Against Ciprofloxacin-Resistant Enterobacteriaceae from Community-Acquired Urinary-Tract Infections. Pistiki A, Tsaganos T, Galani I, Giamarellos-Bourboulis EJ.Infect Dis Ther. 2015 Dec;4(4):425-32. doi: 10.1007/s40121-015-0089-3. Epub 2015 Sep 21. PMID: 26391612 Free PMC Article5:An LC-MS/MS method for simultaneous determination of cefprozil diastereomers in human plasma and its application for the bioequivalence study of two cefprozil tablets in healthy Chinese volunteers. Liu M, Ma JY, Zhang Y, Wang X, Zhao H, Du A, Yang M, Meng L, Deng M, Liu H.Biomed Chromatogr. 2016 Mar;30(3):288-93. doi: 10.1002/bmc.3547. Epub 2015 Aug 27. PMID: 26129932 6:Different approaches in manipulating ratio spectra applied for the analysis of Cefprozil in presence of its alkaline-induced degradation product: a comparative study. Attia KA, Nassar MW, El-Zeiny MB, Serag A.Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jun 15;145:289-94. doi: 10.1016/j.saa.2015.03.038. Epub 2015 Mar 10. PMID: 25791886 7:Synthesis of two thermo-responsive copolymers forming recyclable aqueous two-phase systems and its application in cefprozil partition. Hou D, Cao X.J Chromatogr A. 2014 Jul 4;1349:30-6. doi: 10.1016/j.chroma.2014.04.075. Epub 2014 Apr 28. PMID: 24857035 8:HPLC determination of cefprozil in tablets using monolithic and C18 silica columns. Can NO.J Sep Sci. 2011 Aug;34(16-17):2223-31. doi: 10.1002/jssc.201100170. Epub 2011 May 6. PMID: 21557474 9:Spectrophotometric methods for the determination of cefprozil in bulk and dosage form. Gadkariem EA, Mutasim MM, Ibrahim KE, El-Obeid HA.Int J Biomed Sci. 2009 Sep;5(3):267-74. PMID: 23675147 Free PMC Article10:The stability of cefprozil in oral suspension CEFZIL. Jelińska A, Medenecka B, Zajac M, Knajsiak M.Acta Pol Pharm. 2008 Mar-Apr;65(2):261-5. PMID: 18666435 Free Article