Ertapenem
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MedKoo CAT#: 562875

CAS#: 153832-46-3

Description: Ertapenem is a parenteral carbapenem that is highly resistant to inactivation by a wide variety of beta-lactamases and that has a broad spectrum of antimicrobial activity.


Chemical Structure

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Ertapenem
CAS# 153832-46-3

Theoretical Analysis

MedKoo Cat#: 562875
Name: Ertapenem
CAS#: 153832-46-3
Chemical Formula: C22H25N3O7S
Exact Mass: 475.1413
Molecular Weight: 475.51
Elemental Analysis: C, 55.57; H, 5.30; N, 8.84; O, 23.55; S, 6.74

Price and Availability

Size Price Availability Quantity
200.0mg USD 450.0 2 Weeks
500.0mg USD 950.0 2 Weeks
1.0g USD 1650.0 2 Weeks
2.0g USD 2950.0 2 Weeks
5.0g USD 5450.0 2 Weeks
10.0g USD 7950.0 2 Weeks
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Synonym: Ertapenem; Invanz; MK-0826; MK 0826; MK0826;

IUPAC/Chemical Name: (4R,5S,6S)-3-[(3S,5S)-5-[(3-Carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

InChi Key: JUZNIMUFDBIJCM-ANEDZVCMSA-N

InChi Code: InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1

SMILES Code: O=C(C(N12)=C(S[C@@H]3CN[C@H](C(NC4=CC=CC(C(O)=O)=C4)=O)C3)[C@H](C)[C@]2([H])[C@@H]([C@H](O)C)C1=O)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: Soluble in DMSO

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

Product Data:

Biological target: Ertapenem (L-749345), a long-acting Carbapenem, is a β-lactam antibiotic with a broad antibacterial spectrum.
In vitro activity: The pharmacodynamic activity of ertapenem against MDR ESBL-producing E. coli, simulating free serum concentrations, is displayed in Table 2. Ertapenem T.MIC 98% (ertapenem MICs 0.25 mg/L) resulted in bactericidal (3 log10 killing) activity at 6, 12, 24 and 48 h against all six strains. With all six strains, rapid eradication of the organisms from the in vitro model (below the level of detection) occurred by the 2 h mark (data not shown), which was followed by slow regrowth of the majority of the strains (5 of 6) over 12, 24 and 48 h time points (despite re-dosing ertapenem at 24 h) (Table 2). Despite limited regrowth, ertapenem achieved a bactericidal effect against all strains at all tested time points over the 48 h study period (Table 2). The observed MICs for E. coli of ertapenem studied in the in vitro model did not change during the 48 h period, even for strains where minor regrowth occurred (Table 2). Reference: J Antimicrob Chemother. 2008 Mar;61(3):643-6. https://pubmed.ncbi.nlm.nih.gov/18238885/
In vivo activity: No rat died or lost more than 20% of its body weight during the experiment. The adhesion scores of the groups were determined as median 2.5 (range: 1–3) in group 1, 11.4 (range: 6–15) in group 2, 4.67 (range: 1–6) in group 3, and 2.5 (range: 1–3) in group 4. The adhesion scores of the groups are shown in Figure 1. At the end of the antibiotic treatment, the decrease in the adhesion score was statistically significant (p<0.001). All the isolated microorganisms were identified as sensitive to ertapenem. Reference: Ulus Travma Acil Cerrahi Derg. 2019 Sep;25(5):427-432. https://pubmed.ncbi.nlm.nih.gov/31475323/

Preparing Stock Solutions

The following data is based on the product molecular weight 475.51 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: 1. Zhanel GG, Baudry P, Vashisht V, Laing N, Noreddin AM, Hoban DJ. Pharmacodynamic activity of ertapenem versus multidrug-resistant genotypically characterized extended-spectrum beta-lactamase-producing Escherichia coli using an in vitro model. J Antimicrob Chemother. 2008 Mar;61(3):643-6. doi: 10.1093/jac/dkm533. Epub 2008 Jan 31. PMID: 18238885. 2. Borbone S, Cascone C, Santagati M, Mezzatesta ML, Stefani S. Bactericidal activity of ertapenem against major intra-abdominal pathogens. Int J Antimicrob Agents. 2006 Nov;28(5):396-401. doi: 10.1016/j.ijantimicag.2006.07.018. Epub 2006 Oct 11. PMID: 17045463. 3. Göl Serin B, Köse Ş, Yilmaz O, Yildirim M, Akbulut I, Serin Senger S, Akkoçlu G, Diniz G, Serin S. An evaluation of the effect of ertapenem in rats with sepsis created by cecal ligation and puncture. Ulus Travma Acil Cerrahi Derg. 2019 Sep;25(5):427-432. English. doi: 10.5505/tjtes.2018.26050. PMID: 31475323.
In vitro protocol: 1. Zhanel GG, Baudry P, Vashisht V, Laing N, Noreddin AM, Hoban DJ. Pharmacodynamic activity of ertapenem versus multidrug-resistant genotypically characterized extended-spectrum beta-lactamase-producing Escherichia coli using an in vitro model. J Antimicrob Chemother. 2008 Mar;61(3):643-6. doi: 10.1093/jac/dkm533. Epub 2008 Jan 31. PMID: 18238885. 2. Borbone S, Cascone C, Santagati M, Mezzatesta ML, Stefani S. Bactericidal activity of ertapenem against major intra-abdominal pathogens. Int J Antimicrob Agents. 2006 Nov;28(5):396-401. doi: 10.1016/j.ijantimicag.2006.07.018. Epub 2006 Oct 11. PMID: 17045463.
In vivo protocol: 1. Göl Serin B, Köse Ş, Yilmaz O, Yildirim M, Akbulut I, Serin Senger S, Akkoçlu G, Diniz G, Serin S. An evaluation of the effect of ertapenem in rats with sepsis created by cecal ligation and puncture. Ulus Travma Acil Cerrahi Derg. 2019 Sep;25(5):427-432. English. doi: 10.5505/tjtes.2018.26050. PMID: 31475323.

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1: Saunte DML, Jemec GBE. Hidradenitis Suppurativa: Advances in Diagnosis and Treatment. JAMA. 2017 Nov 28;318(20):2019-2032. doi: 10.1001/jama.2017.16691. Review. PubMed PMID: 29183082.

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8: Andersen RK, Jemec GB. Treatments for hidradenitis suppurativa. Clin Dermatol. 2017 Mar - Apr;35(2):218-224. doi: 10.1016/j.clindermatol.2016.10.018. Epub 2016 Oct 27. Review. PubMed PMID: 28274363.

9: Zelyas N, Gee S, Nilsson B, Bennett T, Rennie R. Infections Caused by Actinomyces neuii: A Case Series and Review of an Unusual Bacterium. Can J Infect Dis Med Microbiol. 2016;2016:6017605. doi: 10.1155/2016/6017605. Epub 2016 Feb 29. Review. PubMed PMID: 27366175; PubMed Central PMCID: PMC4904567.

10: Veillette JJ, Van Epps P. Ertapenem-Induced Hallucinations and Delirium in an Elderly Patient. Consult Pharm. 2016 Apr;31(4):207-14. doi: 10.4140/TCP.n.2016.207. Review. PubMed PMID: 27056357.

11: Candel FJ, Julián-Jiménez A, González-Del Castillo J. Current status in outpatient parenteral antimicrobial therapy: a practical view. Rev Esp Quimioter. 2016 Apr;29(2):55-68. Epub 2016 Mar 25. Review. PubMed PMID: 27014770.

12: Sotgiu G, D'Ambrosio L, Centis R, Tiberi S, Esposito S, Dore S, Spanevello A, Migliori GB. Carbapenems to Treat Multidrug and Extensively Drug-Resistant Tuberculosis: A Systematic Review. Int J Mol Sci. 2016 Mar 12;17(3):373. doi: 10.3390/ijms17030373. Review. PubMed PMID: 26985890; PubMed Central PMCID: PMC4813232.

13: Pedroso TM, Salgado HR. A Critical Review of Analytical Methods for Determination of Ertapenem Sodium. Crit Rev Anal Chem. 2016;46(1):15-21. doi: 10.1080/10408347.2014.937850. Review. PubMed PMID: 26857445.

14: Brook I. Spectrum and treatment of anaerobic infections. J Infect Chemother. 2016 Jan;22(1):1-13. doi: 10.1016/j.jiac.2015.10.010. Epub 2015 Nov 24. Review. PubMed PMID: 26620376.

15: Bettoli V, Join-Lambert O, Nassif A. Antibiotic Treatment of Hidradenitis Suppurativa. Dermatol Clin. 2016 Jan;34(1):81-9. doi: 10.1016/j.det.2015.08.013. Review. PubMed PMID: 26617361.

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18: Apodaca K, Baker J, Bin-Bilal H, Raskin Y, Quinn DK. Ertapenem-Induced Delirium: A Case Report and Literature Review. Psychosomatics. 2015 Sep-Oct;56(5):561-6. doi: 10.1016/j.psym.2015.02.002. Epub 2015 Feb 12. Review. PubMed PMID: 26002226.

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Ertapenem

200.0mg / USD 450.0