Product Name

Ertapenem Sodium

Name: Ertapenem Sodium
SKU: 153773-82-1

CAS Number

153773-82-1

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Product Name:

Ertapenem Sodium

CAS Number:

153773-82-1

Indication:

For the treatment the following moderate to severe infections caused by susceptible isolates of the designated microorganisms: (1) complicated intra-abdominal infections due to Escherichia coli, Clostridium clostridioforme, Eubacterium lentum, Peptostreptococcus species, Bacteroides fragilis, Bacteroides distasonis, Bacteroides ovatus, Bacteroides thetaiotaomicron, or Bacteroides uniformis, (2) complicated skin and skin structure infections, including diabetic foot infections without osteomyelitis due to Staphylococcus aureus (methicillin susceptible isolates only), Streptococcus agalactiae, Streptococcus pyogenes, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Bacteroides fragilis, Peptostreptococcus species, Porphyromonas asaccharolytica, or Prevotella bivia, (3) community acquired pneumonia due to Streptococcus pneumoniae (penicillin susceptible isolates only) including cases with concurrent bacteremia, Haemophilus influenzae (beta-lactamase negative isolates only), or Moraxella catarrhalis, (4) complicated urinary tract infections including pyelonephritis due to Escherichia coli, including cases with concurrent bacteremia, or Klebsiella pneumoniae, (5) acute pelvic infections including postpartum endomyometritis, septic abortion and post surgical gynecologic infections due to Streptococcus agalactiae, Escherichia coli, Bacteroides fragilis, Porphyromonas asaccharolytica, Peptostreptococcus species, or Prevotella bivia.

Mode of Action:

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.

Pharmacodynamics:

Ertapenem has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria.

Metabolism:

The major metabolite is the inactive ring-opened derivative formed by hydrolysis of the β-lactam ring. Ertapenem did not inhibit metabolism mediated by cytochrome P450 (CYP) isoforms 1A2, 2C9, 2C19, 2D6, 2E1, or 3A4 when evaluated by in vitro studies in human liver microsomes. Ertapenem is neither a substrate nor an inhibitor of P-glycoprotein or cytochrome P450 enzymes; significant drug interactions between ertapenem and drugs handled by these systems are not expected [PMID: 15150180]

IUPAC:

1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S, 5S)-5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-, monosodium salt, (4R, 5S, 6S)- 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-, monosodium salt, (4R-(3(3S*, 5S*), 4alpha, 5beta, 6beta(R*)))-

ATC:

J01DH03

PubChem:

23674512

DrugBank:

DB00303

Formula:

C22-H25-N3-O7-S.Na

Molecular Mass:

497.5016

Synonyms:

Ertapenem monosodium, Ertapenem sodium, Invanz, L 749345, MK 0826, MK 826, UNII-2T90KE67L0

SMILES:

C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H]([NH2+]C3)C(=O)Nc4cccc(c4)C(=O)[O-])C(=O)[O-])[C@@H](C)O.[Na+]

AHFS Code:

08:12.07.08

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

General Reference:

Nix DE, Majumdar AK, DiNubile MJ: Pharmacokinetics and pharmacodynamics of ertapenem: an overview for clinicians. J Antimicrob Chemother. 2004 Jun;53 Suppl 2:ii23-8. [PubMed:15150180

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Ertapenem Sodium

153773-82-1

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