Ertapenem Sodium

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Ertapenem Sodium
Category Antibiotics
Catalog number BBF-03993
CAS 153773-82-1
Molecular Weight 497.50
Molecular Formula C22H24N3NaO7S
Purity 95% by HPLC

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BBF-03993 1 g $439 In stock
BBF-03993 5 g $999 In stock

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Description

Ertapenem Sodium is the sodium salt of ertapenem. Ertapenem has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3. Ertapenem is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Ertapenem is hydrolyzed by metallo-beta-lactamases. Ertapenem has been shown to be active against most isolates of the following microorganisms in vitro and in clinical infections.

Specification

Related CAS 153832-38-3 (disodium) 153832-46-3 (free acid)
Synonyms Invanz; Ertapenem sodium salt; MK-0826
Storage Store at -20°C
IUPAC 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
Canonical SMILES CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)O)C(C)O.[Na+]
InChI 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
InChI Key ZXNAQFZBWUNWJM-HRXMHBOMSA-M

Properties

Appearance White to Light Yellow Solid
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 813.9°C at 760 mmHg
Solubility Soluble in DMSO

Reference Reading

1.Stability of Ertapenem 100 mg/mL in Manufacturer's Glass Vials or Syringes at 4°C and 23°C.
Walker SE1, Law S2, Perks W3, Iazzetta J4. Can J Hosp Pharm. 2015 Mar-Apr;68(2):121-6.
in English, FrenchCONTEXTE: Il a été démontré que l’administration prophylactique d’une dose unique de 1 g d’ertapénem par voie intraveineuse réduit les risques de sepsis après une biopsie de la prostate.
2.Stability of ertapenem 100 mg/mL in polypropylene syringes stored at 25, 4, and -20 °C.
Jain JG1, Sutherland C1, Nicolau DP1, Kuti JL2. Am J Health Syst Pharm. 2014 Sep 1;71(17):1480-4. doi: 10.2146/ajhp130664.
PURPOSE: The stability of ertapenem solution in syringes at room, refrigerator, and freezer temperatures was determined to establish options for extended storage.
3.Community-acquired urinary tract infections in children: pathogens, antibiotic susceptibility and seasonal changes.
Yolbaş I1, Tekin R, Kelekci S, Tekin A, Okur MH, Ece A, Gunes A, Sen V. Eur Rev Med Pharmacol Sci. 2013 Apr;17(7):971-6.
AIM: Urinary tract infections (UTIs) are common infections affecting children. The aim of our study is to determine microorganisms that cause community-acquired urinary tract infections and their antibiotic susceptibility in children.
4.A Critical Review of Analytical Methods for Determination of Ertapenem Sodium.
Pedroso TM1, Salgado HR1. Crit Rev Anal Chem. 2016 Jan 2;46(1):15-21. doi: 10.1080/10408347.2014.937850.
Antimicrobials have unquestionable importance in the control of many diseases; however the constant concern with evolution of resistant microorganisms is increasing. Ertapenem sodium is a β-lactam antibiotic of the carbapenem class that has a broader activity spectrum than most other β-lactam antimicrobials and is more resistant to the enzyme β-lactamase, which is the main mechanism of resistance of many bacteria. The progress of microbial resistance to existing antibiotics is alarming. Thus we need to preserve antimicrobials that still have activity against these pathogens. In this context, quality control has a key role to ensure the correct dosage, by contributing preventively to minimize the development of resistant microorganisms. Study of the physico-chemical characteristics of the drug and quantification of the content of the active substance are of fundamental importance for the pharmaceutical industry to ensure the quality of the product sold.

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