MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 317782 | Name: Ertapenem Sodium
Featured New

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 Sodium
Ertapenem Sodium
CAS#153773-82-1 (sodium)

Theoretical Analysis

MedKoo Cat#: 317782

Name: Ertapenem Sodium

CAS#: 153773-82-1 (sodium)

Chemical Formula: C22H24N3NaO7S

Exact Mass: 0.0000

Molecular Weight: 497.50

Elemental Analysis: C, 53.11; H, 4.86; N, 8.45; Na, 4.62; O, 22.51; S, 6.45

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to ship
25mg USD 150.00 Ready to ship
50mg USD 250.00 Ready to ship
100mg USD 450.00 Ready to ship
200mg USD 750.00 Ready to ship
500mg USD 1,350.00 Ready to ship
1g USD 2,650.00 Ready to ship
2g USD 4,850.00 Ready to ship
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
153773-82-1 (sodium) 153832-38-3 (disodium) 153832-46-3 (free acid)
Synonym
Ertapenem Sodium; MK 826; MK-826; MK826; MK-0826; MK 0826; MK0826; L 749345; L749345; L-749345; Invanoz; Invanz;
IUPAC/Chemical Name
sodium;3-[[(2S,4S)-4-[[(4R,5S,6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]sulfanyl]pyrrolidine-2-carbonyl]amino]benzoate
InChi Key
ZXNAQFZBWUNWJM-HRXMHBOMSA-M
InChi Code
InChI=1S/C22H25N3O7S.Na/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);/q;+1/p-1/t9-,10-,13+,14+,15-,16-;/m1./s1
SMILES Code
C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)O)[C@@H](C)O.[Na+]
Appearance
Solid powder
Purity
>95% (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, 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
Biological target:
Ertapenem sodium (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/
Solvent mg/mL mM
Solubility
DMSO 100.0 201.01
Water 81.3 163.32
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 497.50 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.
1: Goutelle S, Valour F, Gagnieu MC, Laurent F, Chidiac C, Ferry T; Lyon Bone and Joint Infection Study Group. Population pharmacokinetics and probability of target attainment of ertapenem administered by subcutaneous or intravenous route in patients with bone and joint infection. J Antimicrob Chemother. 2017 Dec 13. doi: 10.1093/jac/dkx477. [Epub ahead of print] PubMed PMID: 29244077. 2: Oztas E, Akpinar MY, Kaplan M. Letter To The Editor: Ertapenem-Induced Acute Pancreatitis in a Cirrhotic Patient. Ochsner J. 2017 Winter;17(4):305. PubMed PMID: 29230108; PubMed Central PMCID: PMC5718436. 3: Lass J, Tamme K, Kipper K, Starkopf J. Dosing of Ertapenem in an Extreme Obesity: A Case Report of 250 kg Patient. Case Rep Crit Care. 2017;2017:5310768. doi: 10.1155/2017/5310768. Epub 2017 Oct 8. PubMed PMID: 29119027; PubMed Central PMCID: PMC5651098. 4: Aydın A, Barış Aykan M, Sağlam K, Veillette JJ. Seizure Induced by Ertapenem in an Elderly Patient with Dementia. Consult Pharm. 2017 Oct 1;32(10):561-562. doi: 10.4140/TCP.n.2017.561. PubMed PMID: 29076446. 5: Patel UC, Fowler MA. Ertapenem-associated neurotoxicity in the Spinal Cord Injury (SCI) population: a case series. J Spinal Cord Med. 2017 Sep 6:1-10. doi: 10.1080/10790268.2017.1368960. [Epub ahead of print] PubMed PMID: 28874102. 6: Monogue ML, Nicolau DP. Translational Efficacy of Humanized Exposures of Cefepime, Ertapenem, and Levofloxacin against Extended-Spectrum-β-Lactamase-Producing Escherichia coli in a Murine Model of Complicated Urinary Tract Infection. Antimicrob Agents Chemother. 2017 Oct 24;61(11). pii: e01329-17. doi: 10.1128/AAC.01329-17. Print 2017 Nov. PubMed PMID: 28848015; PubMed Central PMCID: PMC5655047. 7: Tanır Basaranoglu S, Ozsurekci Y, Aykac K, Arıkan KO, Buyukcam A, Cengiz AB, Ceyhan M, Kara A. Add-On Therapy with Ertapenem in Infections with Multidrug Resistant Gram-Negative Bacteria: Pediatric Experience. Case Rep Infect Dis. 2017;2017:8096420. doi: 10.1155/2017/8096420. Epub 2017 Jul 26. PubMed PMID: 28815094; PubMed Central PMCID: PMC5549487. 8: Lee YC, Huang YJ, Hung MC, Hung SC, Hsiao CY, Cho HL, Lai LF, Tong SH, Wang JT. Risk factors associated with the development of seizures among adult patients treated with ertapenem: A matched case-control study. PLoS One. 2017 Jul 31;12(7):e0182046. doi: 10.1371/journal.pone.0182046. eCollection 2017. PubMed PMID: 28759588; PubMed Central PMCID: PMC5536326. 9: Somboon K, Niramitranon J, Pongprayoon P. Probing the binding affinities of imipenem and ertapenem for outer membrane carboxylate channel D1 (OccD1) from P. aeruginosa: simulation studies. J Mol Model. 2017 Aug;23(8):227. doi: 10.1007/s00894-017-3400-2. Epub 2017 Jul 17. PubMed PMID: 28717993. 10: van Rijn SP, Srivastava S, Wessels MA, van Soolingen D, Alffenaar JC, Gumbo T. Sterilizing Effect of Ertapenem-Clavulanate in a Hollow-Fiber Model of Tuberculosis and Implications on Clinical Dosing. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: e02039-16. doi: 10.1128/AAC.02039-16. Print 2017 Sep. PubMed PMID: 28696238; PubMed Central PMCID: PMC5571313. 11: Docobo RA, Bukhari S, Qutrio Baloch Z. Ertapenem-Induced Thrombocytosis. Cureus. 2017 May 19;9(5):e1263. doi: 10.7759/cureus.1263. PubMed PMID: 28652947; PubMed Central PMCID: PMC5476495. 12: Kumar MRR, Arunagirinathan N, Vignesh R, Balakrishnan P, Solomon S, Sunil SS. Ertapenem for multiple β-lactamases producing Gram-negative bacteria causing urinary tract infections in HIV patients. J Res Med Sci. 2017 May 30;22:69. doi: 10.4103/jrms.JRMS_884_16. eCollection 2017. PubMed PMID: 28616056; PubMed Central PMCID: PMC5461584. 13: Seo YB, Lee J, Kim YK, Lee SS, Lee JA, Kim HY, Uh Y, Kim HS, Song W. Randomized controlled trial of piperacillin-tazobactam, cefepime and ertapenem for the treatment of urinary tract infection caused by extended-spectrum beta-lactamase-producing Escherichia coli. BMC Infect Dis. 2017 Jun 7;17(1):404. doi: 10.1186/s12879-017-2502-x. PubMed PMID: 28592240; PubMed Central PMCID: PMC5463388. 14: Malaisri C, Phuphuakrat A, Wibulpolprasert A, Santanirand P, Kiertiburanakul S. A randomized controlled trial of sitafloxacin vs. ertapenem as a switch therapy after treatment for acute pyelonephritis caused by extended-spectrum β-lactamase-producing Escherichia coli: A pilot study. J Infect Chemother. 2017 Aug;23(8):556-562. doi: 10.1016/j.jiac.2017.05.005. Epub 2017 Jun 3. PubMed PMID: 28587974. 15: Seitz M, Stief C, Waidelich R, Bader M, Tilki D. Transrectal ultrasound guided prostate biopsy in the era of increasing fluoroquinolone resistance: prophylaxis with single-dose ertapenem. World J Urol. 2017 Nov;35(11):1681-1688. doi: 10.1007/s00345-017-2043-3. Epub 2017 May 3. PubMed PMID: 28470334. 16: Bloomfield MG, Page MJ, McLachlan AG, Studd RC, Blackmore TK. Routine Ertapenem Prophylaxis for Transrectal Ultrasound Guided Prostate Biopsy does Not Select for Carbapenem Resistant Organisms: A Prospective Cohort Study. J Urol. 2017 Aug;198(2):362-368. doi: 10.1016/j.juro.2017.03.077. Epub 2017 Mar 10. PubMed PMID: 28288838. 17: Dupont H, Choinier P, Roche D, Adiba S, Sookdeb M, Branger C, Denamur E, Mammeri H. Structural Alteration of OmpR as a Source of Ertapenem Resistance in a CTX-M-15-Producing Escherichia coli O25b:H4 Sequence Type 131 Clinical Isolate. Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: e00014-17. doi: 10.1128/AAC.00014-17. Print 2017 May. PubMed PMID: 28264855; PubMed Central PMCID: PMC5404536. 18: Rattanaumpawan P, Werarak P, Jitmuang A, Kiratisin P, Thamlikitkul V. Efficacy and safety of de-escalation therapy to ertapenem for treatment of infections caused by extended-spectrum-β-lactamase-producing Enterobacteriaceae: an open-label randomized controlled trial. BMC Infect Dis. 2017 Mar 1;17(1):183. doi: 10.1186/s12879-017-2284-1. PubMed PMID: 28249572; PubMed Central PMCID: PMC5333449. 19: Sutton SS, Jumper M, Cook S, Edun B, Wyatt MD. Ertapenem-Induced Encephalopathy in a Patient With Normal Renal Function. J Investig Med High Impact Case Rep. 2017 Jan 1;5(1):2324709616689376. doi: 10.1177/2324709616689376. eCollection 2017 Jan-Mar. PubMed PMID: 28203577; PubMed Central PMCID: PMC5298517. 20: van Rijn SP, Zuur MA, van Altena R, Akkerman OW, Proost JH, de Lange WC, Kerstjens HA, Touw DJ, van der Werf TS, Kosterink JG, Alffenaar JW. Pharmacokinetic Modeling and Limited Sampling Strategies Based on Healthy Volunteers for Monitoring of Ertapenem in Patients with Multidrug-Resistant Tuberculosis. Antimicrob Agents Chemother. 2017 Mar 24;61(4). pii: e01783-16. doi: 10.1128/AAC.01783-16. Print 2017 Apr. PubMed PMID: 28137814; PubMed Central PMCID: PMC5365678.