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MedKoo Cat#: 464265 | Name: Cefprozil-d4
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Description:

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

Cefprozil-d4 is intended for use as an internal standard for the quantification of cefprozil by GC- or LC-MS. Cefprozil is an orally bioavailable, second generation, broad-spectrum cephalosporin antibiotic that inhibits the growth of both Gram-positive and Gram-negative bacteria. 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. Cefprozil binds to penicillin-binding proteins (PBPs), which disrupts their ability to cross-link peptidoglycan and leads to weakened bacterial cell walls. Formulations containing cefprozil have been used in the treatment of respiratory tract, skin, and other bacterial infections.

Chemical Structure

Cefprozil-d4
CAS#1426173-48-9 (deuterated forms)

Theoretical Analysis

MedKoo Cat#: 464265

Name: Cefprozil-d4

CAS#: 1426173-48-9 (deuterated forms)

Chemical Formula: C18H15D4N3O5S

Exact Mass: 393.1296

Molecular Weight: 393.45

Elemental Analysis: C, 54.95; H, 5.89; N, 10.68; O, 20.33; S, 8.15

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
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Related CAS #
92665-29-7 (free) 121123-17-9 (hydrate) 1426173-48-9 (deuterated forms)
Synonym
Cefprozil-d4; Cefprozil d4;
IUPAC/Chemical Name
(6R,7R)-7-((R)-2-amino-2-(4-hydroxyphenyl-2,3,5,6-d4)acetamido)-8-oxo-3-((E)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
WDLWHQDACQUCJR-BMKVJPEASA-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/i4D,5D,6D,7D
SMILES Code
O=C(C1=C(CS[C@@]([H])(N1C2=O)[C@@H]2NC([C@@H](C3=C(C([2H])=C(C([2H])=C3[2H])O)[2H])N)=O)/C=C/C)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 393.45 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
1: Yang L, Zhou G, Liu J, Song J, Zhang Z, Huang Q, Wei F. Tanshinone I and Tanshinone IIA/B attenuate LPS-induced mastitis via regulating the NF-κB. Biomed Pharmacother. 2021 Feb 9;137:111353. doi: 10.1016/j.biopha.2021.111353. Epub ahead of print. PMID: 33578236. 2: Lin PP, Wang CJ, Liu YP, Li T, Gao XM, Ma YP, Shi P, Li X, Wang LX, Cao Y. Pharmacokinetics and Bioequivalence of Cefprozil for Suspension and Granule Formulation in Healthy Chinese Volunteers: Two Single-Dose Crossover Studies. Adv Ther. 2021 Feb;38(2):1130-1142. doi: 10.1007/s12325-020-01593-7. Epub 2020 Dec 19. PMID: 33340343. 3: Doshi K, Pandya N, Datt M. In silico assessment of natural products and approved drugs as potential inhibitory scaffolds targeting aminoacyl-tRNA synthetases from Plasmodium. 3 Biotech. 2020 Nov;10(11):470. doi: 10.1007/s13205-020-02460-6. Epub 2020 Oct 12. PMID: 33088666; PMCID: PMC7550503. 4: Jarmusch AK, Vrbanac A, Momper JD, Ma JD, Alhaja M, Liyanage M, Knight R, Dorrestein PC, Tsunoda SM. Enhanced Characterization of Drug Metabolism and the Influence of the Intestinal Microbiome: A Pharmacokinetic, Microbiome, and Untargeted Metabolomics Study. Clin Transl Sci. 2020 Sep;13(5):972-984. doi: 10.1111/cts.12785. Epub 2020 Apr 13. PMID: 32216086; PMCID: PMC7485946. 5: Koo H, Hakim JA, Crossman DK, Kumar R, Lefkowitz EJ, Morrow CD. Individualized recovery of gut microbial strains post antibiotics. NPJ Biofilms Microbiomes. 2019 Oct 11;5(1):30. doi: 10.1038/s41522-019-0103-8. PMID: 31632686; PMCID: PMC6789009. 6: Jang JH, Jeong SH, Cho HY, Lee YB. Population Pharmacokinetics of Cis-, Trans-, and Total Cefprozil in Healthy Male Koreans. Pharmaceutics. 2019 Oct 14;11(10):531. doi: 10.3390/pharmaceutics11100531. PMID: 31614996; PMCID: PMC6836086. 7: Yehia AM, Elbalkiny HT, Riad SM, Elsaharty YS. Chemometrics for resolving spectral data of cephalosporines and tracing their residue in waste water samples. Spectrochim Acta A Mol Biomol Spectrosc. 2019 Aug 5;219:436-443. doi: 10.1016/j.saa.2019.04.081. Epub 2019 Apr 30. PMID: 31063958. 8: Fotoulaki M, Giza S, Jirsa M, Grammatikopoulos T, Miquel R, Hytiroglou P, Tsitouridis I, Knisely AS. Beyond an Obvious Cause of Cholestasis in a Toddler: Compound Heterozygosity for ABCB11 Mutations. Pediatrics. 2019 May;143(5):e20182146. doi: 10.1542/peds.2018-2146. PMID: 31015375. 9: Bathini L, Jandoc R, Kuwornu P, McArthur E, Weir MA, Sood MM, Battistella M, Muanda FT, Liu A, Jain AK, Garg AX. Clinical Outcomes of Failing to Dose-Reduce Cephalosporin Antibiotics in Older Adults with CKD. Clin J Am Soc Nephrol. 2019 Feb 7;14(2):197-205. doi: 10.2215/CJN.10710918. Epub 2019 Jan 10. PMID: 30630861; PMCID: PMC6390923. 10: Eser Simsek I, Tuba Cogurlu M, Aydogan M. Suspected Reaction with Cephalosporin May Be a Predictive Factor for β-Lactam Allergy in Children. Int Arch Allergy Immunol. 2019;178(3):248-254. doi: 10.1159/000494506. Epub 2018 Dec 5. PMID: 30517941. 11: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Cefprozil. 2018 Oct 31. PMID: 30000469. 12: He G, Mai L, Wang X. Development and Validation of an HPLC-MS/MS Method for Rapid Simultaneous Determination of Cefprozil Diastereomers in Human Plasma. Int J Anal Chem. 2018 Sep 13;2018:6959761. doi: 10.1155/2018/6959761. PMID: 30302091; PMCID: PMC6158942. 13: Leung AKC, Wong AHC, Hon KL. Community-Acquired Pneumonia in Children. Recent Pat Inflamm Allergy Drug Discov. 2018;12(2):136-144. doi: 10.2174/1872213X12666180621163821. PMID: 29932038. 14: Chen J, Ding Z, Pan H, Cao X. Development of pH-responsive polymer and citrate aqueous two-phase system for extractive bioconversion of cefprozil. Talanta. 2017 Nov 1;174:256-264. doi: 10.1016/j.talanta.2017.05.027. Epub 2017 May 12. PMID: 28738576. 15: Attia KA, Nassar MW, El-Zeiny MB, Serag A. Molecular and Quantum Mechanical Study for the Separation of Cefprozil in the Presence of Its Alkaline Degradation Product Using RP-HPLC with UV Detection. J AOAC Int. 2017 Mar 1;100(2):392-399. doi: 10.5740/jaoacint.16-0246. Epub 2016 Nov 17. PMID: 28118569. 16: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Cephalosporins. 2017 Jan 9. PMID: 31643977. 17: Raymond F, Déraspe M, Boissinot M, Bergeron MG, Corbeil J. Partial recovery of microbiomes after antibiotic treatment. Gut Microbes. 2016 Sep 2;7(5):428-34. doi: 10.1080/19490976.2016.1216747. Epub 2016 Aug 5. Erratum for: doi: 10.1038/ismej.2015.148. PMID: 27494088; PMCID: PMC5154369. 18: Jia FF, Tan ZR, McLeod HL, Chen Y, Ou-Yang DS, Zhou HH. Effects of quercetin on pharmacokinetics of cefprozil in Chinese-Han male volunteers. Xenobiotica. 2016 Oct;46(10):896-900. doi: 10.3109/00498254.2015.1132792. Epub 2016 Feb 29. PMID: 26928207. 19: 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 Apr 15;159:1-6. doi: 10.1016/j.saa.2016.01.026. Epub 2016 Jan 21. PMID: 26814624. 20: 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. PMID: 26391612; PMCID: PMC4675762.

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