Ertapenem | CAS#153832-46-3 | parenteral carbapenem

MedKoo Cat#: 562875 | Name: Ertapenem

Description:

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

Ertapenem is a broad-spectrum carbapenem antibiotic that exerts its bactericidal activity by inhibiting bacterial cell wall synthesis through binding to penicillin-binding proteins (PBPs). It shows potent in vitro activity against a wide range of Gram-negative and Gram-positive aerobes and anaerobes, including Escherichia coli (MIC90: 0.03–0.12 µg/mL), Klebsiella pneumoniae (MIC90: 0.06–0.12 µg/mL), Streptococcus pneumoniae (MIC90: 0.03–0.06 µg/mL), and Bacteroides fragilis (MIC90: 0.25–0.5 µg/mL). However, it lacks activity against non-fermenters such as Pseudomonas aeruginosa and Acinetobacter spp. due to poor binding affinity to their PBPs and active efflux. Ertapenem is highly stable to most β-lactamases, including extended-spectrum β-lactamases (ESBLs), making it effective against many multidrug-resistant organisms. It is used clinically for complicated intra-abdominal infections, skin and soft tissue infections, community-acquired pneumonia, and urinary tract infections.

Chemical Structure

Ertapenem

CAS#153832-46-3 (free acid)

Theoretical Analysis

MedKoo Cat#: 562875

Name: Ertapenem

CAS#: 153832-46-3 (free acid)

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
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 1,650.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,250.00	2 Weeks

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Related CAS #

153773-82-1 (sodium) 153832-38-3 (disodium) 153832-46-3 (free acid)

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

More Info

Product Data

Product Data

Instruction

View handling instruction

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.

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:

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.

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. 2: Lother SA, Press N. Once-Daily Treatments for Methicillin-Susceptible Staphylococcus aureus Bacteremia: Are They Good Enough? Curr Infect Dis Rep. 2017 Sep 23;19(11):43. doi: 10.1007/s11908-017-0599-0. Review. PubMed PMID: 28942574. 3: Deshayes S, Coquerel A, Verdon R. Neurological Adverse Effects Attributable to β-Lactam Antibiotics: A Literature Review. Drug Saf. 2017 Dec;40(12):1171-1198. doi: 10.1007/s40264-017-0578-2. Review. PubMed PMID: 28755095. 4: Bos JC, van Hest RM, Prins JM. Pharmacokinetics of Antibiotics in Sub-Saharan African Patient Populations: A Systematic Review. Ther Drug Monit. 2017 Aug;39(4):387-398. doi: 10.1097/FTD.0000000000000418. Review. PubMed PMID: 28703719. 5: Takimoto K, Wang Q, Suzuki D, Katayama M, Hayashi Y. Clinical efficacy of piperacillin/tazobactam in the treatment of complicated skin and soft tissue infections. Expert Opin Pharmacother. 2017 Jul;18(10):1027-1034. doi: 10.1080/14656566.2017.1341491. Epub 2017 Jun 23. Review. PubMed PMID: 28627952. 6: Murray CK. Field Wound Care: Prophylactic Antibiotics. Wilderness Environ Med. 2017 Jun;28(2S):S90-S102. doi: 10.1016/j.wem.2016.12.009. Review. PubMed PMID: 28601215. 7: El-Gamal MI, Brahim I, Hisham N, Aladdin R, Mohammed H, Bahaaeldin A. Recent updates of carbapenem antibiotics. Eur J Med Chem. 2017 May 5;131:185-195. doi: 10.1016/j.ejmech.2017.03.022. Epub 2017 Mar 16. Review. PubMed PMID: 28324783. 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. 16: Markakis K, Bowling FL, Boulton AJ. The diabetic foot in 2015: an overview. Diabetes Metab Res Rev. 2016 Jan;32 Suppl 1:169-78. doi: 10.1002/dmrr.2740. Review. PubMed PMID: 26451519. 17: Selva Olid A, Solà I, Barajas-Nava LA, Gianneo OD, Bonfill Cosp X, Lipsky BA. Systemic antibiotics for treating diabetic foot infections. Cochrane Database Syst Rev. 2015 Sep 4;(9):CD009061. doi: 10.1002/14651858.CD009061.pub2. Review. PubMed PMID: 26337865. 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. 19: Jeon JH, Lee JH, Lee JJ, Park KS, Karim AM, Lee CR, Jeong BC, Lee SH. Structural basis for carbapenem-hydrolyzing mechanisms of carbapenemases conferring antibiotic resistance. Int J Mol Sci. 2015 Apr 29;16(5):9654-92. doi: 10.3390/ijms16059654. Review. PubMed PMID: 25938965; PubMed Central PMCID: PMC4463611. 20: Cantón R, Canut A, Morosini MI, Oliver A. Breakpoints for carbapenemase-producing Enterobacteriaceae: is the problem solved? Enferm Infecc Microbiol Clin. 2014 Dec;32 Suppl 4:33-40. doi: 10.1016/S0213-005X(14)70172-7. Review. PubMed PMID: 25542050.

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MedKoo CAT#: 525260

CAS#: Unknown