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MedKoo Cat#: 317399 | Name: Cefprozil
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Cefprozil
CAS# 92665-29-7 (free)

Theoretical Analysis

MedKoo Cat#: 317399

Name: Cefprozil

CAS#: 92665-29-7 (free)

Chemical Formula: C18H19N3O5S

Exact Mass: 389.1045

Molecular Weight: 389.43

Elemental Analysis: C, 55.52; H, 4.92; N, 10.79; O, 20.54; S, 8.23

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 750.00 2 Weeks
50mg USD 1,250.00 2 Weeks
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Related CAS #
92665-29-7 (free) 121123-17-9 (hydrate) 1426173-48-9 (deuterated forms)
Synonym
Cefprozil; Cefprozil anhydrous; Brisoral; Cefzil; Cefprozilo; Cefprozilum; Procef; cefprozil monohydrate; Arzimol; BMY 28100; BMY-28100; Brisoral;
IUPAC/Chemical 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
InChi Key
WDLWHQDACQUCJR-ZAMMOSSLSA-N
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
SMILES Code
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
Appearance
Solid powder
Purity
≥95% (mixture of cis and trans)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cefprozil is a semi-synthetic broad-spectrum cephalosporin antibiotic, used to treat certain infections caused by bacteria, such as bronchitis and infections of the ears, throat, sinuses, and skin.
In vitro activity:
Cefprozil is an orally active cephalosporin which has demonstrated activity against a wide range of organisms in vitro. It is particularly active against the Gram-positive organisms Streptococcus pyogenes, pneumoniae and agalactiae and against methicillin-susceptible Staphylococcus aureus. Strains of methicillin-resistant S. aureus are not susceptible to cefprozil. Cefprozil is also moderately active against Haemophilus influenzae, Moraxella catarrhalis, Neisseria gonorrhoeae, many Enterobacteriaceae and certain anaerobic organisms, and is relatively stable to hydrolysis by a number of beta-lactamases. Reference: Drugs. 1993 Feb;45(2):295-317. https://dx.doi.org/10.2165/00003495-199345020-00008
In vivo activity:
To simulate the pharmacokinetic profile of cefprozil in children, the renal function of mice was impaired with uranyl nitrate, and a commercially available cefprozil suspension (6 mg/kg of body weight) was administered orally every 12 h. Mice were infected with 10(6) to 10(7) CFU per thigh, and therapy was initiated 2 h later. At 0 and 24 h postinfection, thighs were harvested to determine bacterial density. Survival was assessed during 96 h of therapy. The magnitude of bacterial kill ranged from 0.5 to 4.4 log(10) CFU per thigh over 24 h, and the extent of microbial eradication was dependent on the MIC. Killing of more than 2.6 log(10) CFU per thigh was observed with MICs of < or =3 microg/ml, while either minimal killing or growth was detected with MICs of > or =4 microg/ml. Mortality in untreated control animals was 100%. Animals infected with strains for which the MICs were < or =2 microg/ml survived the infection, whereas MICs exceeding 2 microg/ml resulted in substantial mortality. These studies demonstrate the effectiveness of cefprozil against isolates of the pneumococcus for which the MICs are < or =2 microg/ml using a drug exposure typically observed in children. These data support a susceptibility breakpoint of < or =2 microg/ml for cefprozil. Reference: Antimicrob Agents Chemother. 2000 May;44(5):1291-5. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/10770764/

Preparing Stock Solutions

The following data is based on the product molecular weight 389.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Wiseman LR, Benfield P. Cefprozil. A review of its antibacterial activity, pharmacokinetic properties, and therapeutic potential. Drugs. 1993 Feb;45(2):295-317. doi: 10.2165/00003495-199345020-00008. PMID: 7681376. 2. Thornsberry C. Review of the in vitro antibacterial activity of cefprozil, a new oral cephalosporin. Clin Infect Dis. 1992 Jun;14 Suppl 2:S189-94; discussion S195-6. doi: 10.1093/clinids/14.supplement_2.s189. PMID: 1617037.
In vivo protocol:
1. Nicolau DP, Onyeji CO, Zhong M, Tessier PR, Banevicius MA, Nightingale CH. Pharmacodynamic assessment of cefprozil against Streptococcus pneumoniae: implications for breakpoint determinations. Antimicrob Agents Chemother. 2000 May;44(5):1291-5. doi: 10.1128/AAC.44.5.1291-1295.2000. PMID: 10770764; PMCID: PMC89857.
1: Liu M, Ma JY, Zhang Y, Wang X, Zhao H, Du A, Yang M, Meng L, Deng M, Liu H. 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. Biomed Chromatogr. 2016 Mar;30(3):288-93. doi: 10.1002/bmc.3547. Epub 2015 Aug 27. PubMed PMID: 26129932. 2: Attia KA, Nassar MW, El-Zeiny MB, Serag A. Stability indicating methods for the analysis of cefprozil in the presence of its alkaline induced degradation product. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jan 21;159:1-6. doi: 10.1016/j.saa.2016.01.026. [Epub ahead of print] PubMed PMID: 26814624. 3: Pistiki A, Tsaganos T, Galani I, Giamarellos-Bourboulis EJ. In Vitro Activity of Oral Cephalosporins (Cefprozil and Cefixime) Against Ciprofloxacin-Resistant Enterobacteriaceae from Community-Acquired Urinary-Tract Infections. Infect Dis Ther. 2015 Dec;4(4):425-32. doi: 10.1007/s40121-015-0089-3. Epub 2015 Sep 21. PubMed PMID: 26391612; PubMed Central PMCID: PMC4675762. 4: Attia KA, Nassar MW, El-Zeiny MB, Serag A. Different approaches in manipulating ratio spectra applied for the analysis of Cefprozil in presence of its alkaline-induced degradation product: a comparative study. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jun 15;145:289-94. doi: 10.1016/j.saa.2015.03.038. Epub 2015 Mar 10. PubMed PMID: 25791886. 5: Hou D, Cao X. Synthesis of two thermo-responsive copolymers forming recyclable aqueous two-phase systems and its application in cefprozil partition. J Chromatogr A. 2014 Jul 4;1349:30-6. doi: 10.1016/j.chroma.2014.04.075. Epub 2014 Apr 28. PubMed PMID: 24857035. 6: Can NO. HPLC determination of cefprozil in tablets using monolithic and C18 silica columns. J Sep Sci. 2011 Aug;34(16-17):2223-31. doi: 10.1002/jssc.201100170. Epub 2011 May 6. PubMed PMID: 21557474. 7: Gadkariem EA, Mutasim MM, Ibrahim KE, El-Obeid HA. Spectrophotometric methods for the determination of cefprozil in bulk and dosage form. Int J Biomed Sci. 2009 Sep;5(3):267-74. PubMed PMID: 23675147; PubMed Central PMCID: PMC3614783. 8: Jerath N, Shetty G. Redefining the management of pediatric tonsillopharyngitis with cefprozil. Indian J Pediatr. 2007 Dec;74(12):1105-8. Review. PubMed PMID: 18174646. 9: Bilici A, Karaduman M, Cankir Z. A rare case of hepatitis associated with cefprozil therapy. Scand J Infect Dis. 2007;39(2):190-2. PubMed PMID: 17366046. 10: Smith PF, Tsuji B, Booker BM, Forrest A, Bajic S, Kelchlin P, Bhavnani SM, Jones RN, Ambrose PG. Pharmacodynamics of cefprozil against Haemophilus influenzae in an in vitro pharmacodynamic model. Diagn Microbiol Infect Dis. 2006 Dec;56(4):379-86. Epub 2006 Aug 23. PubMed PMID: 16930921. 11: Alarfaj NA, Abd El-Razeq SA. Flow-injection chemiluminescent determination of cefprozil using Tris (2,2'-bipyridyl) ruthenium (II)-permanganate system. J Pharm Biomed Anal. 2006 Jun 16;41(4):1423-7. Epub 2006 May 6. PubMed PMID: 16682164. 12: Starostecka B. [Assessment of therapeutic effectiveness of Cefprozil in a short 5-day course of empirical antibiotic therapy in ambulatory patients with bacterial infections of the upper respiratory tract and otitis media]. Otolaryngol Pol. 2005;59(1):147-8. Polish. PubMed PMID: 15973798. 13: Baciewicz AM, Chandra R. Cefprozil-induced rash in infectious mononucleosis. Ann Pharmacother. 2005 May;39(5):974-5. Epub 2005 Apr 12. PubMed PMID: 15827073. 14: Park TH, Kim JK, Jee JP, Park JS, Kim CK. HPLC method for simultaneous determination of cefprozil diastereomers in human plasma. J Pharm Biomed Anal. 2004 Sep 21;36(1):243-8. PubMed PMID: 15351073. 15: Carvalho ES, Campos SO, Pignatari SN, Weckx LL. [Efficacy and safety of cefprozil versus cefaclor in the treatment of acute otitis media in pediatric patients]. J Pediatr (Rio J). 1998 Nov-Dec;74(6):461-6. Portuguese. PubMed PMID: 14685589. 16: Jang CH, Park SY. Penetration of cefprozil to middle ear effusion in children with chronic otitis media with effusion. Int J Pediatr Otorhinolaryngol. 2003 Sep;67(9):965-8. PubMed PMID: 12907051. 17: Clark C, Bozdogan B, Peric M, Dewasse B, Jacobs MR, Appelbaum PC. In vitro selection of resistance in Haemophilus influenzae by amoxicillin-clavulanate, cefpodoxime, cefprozil, azithromycin, and clarithromycin. Antimicrob Agents Chemother. 2002 Sep;46(9):2956-62. PubMed PMID: 12183253; PubMed Central PMCID: PMC127454. 18: Nagai K, Davies TA, Jacobs MR, Appelbaum PC. 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. 2002 May;46(5):1273-80. PubMed PMID: 11959556; PubMed Central PMCID: PMC127189. 19: McCarty JM, Pierce PF. Five days of cefprozil versus 10 days of clarithromycin in the treatment of an acute exacerbation of chronic bronchitis. Ann Allergy Asthma Immunol. 2001 Oct;87(4):327-34. PubMed PMID: 11686426. 20: Block SL, Kratzer J, Nemeth MA, Tack KJ. Five-day cefdinir course vs. ten-day cefprozil course for treatment of acute otitis media. Pediatr Infect Dis J. 2000 Dec;19(12 Suppl):S147-52. PubMed PMID: 11144396.

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