| Candidate ID: | R0109 |
| Source ID: | DB00303 |
| Source Type: | approved; investigational |
| Compound Type: |
small molecule
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| Compound Name: |
Ertapenem
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| Synonyms: |
(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid; (4R,5S,6S)-3-((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid; Ertapenem
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| Molecular Formula: |
C22H25N3O7S
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| SMILES: |
[H][C@]12[C@@H](C)C(S[C@]3([H])CN[C@@]([H])(C3)C(=O)NC3=CC=CC(=C3)C(O)=O)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O
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| Structure: |
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| DrugBank Description: |
Ertapenem is a carbapenem antibiotic drug that is marketed under the trade name Invanz by Merck & Co. pharmaceutical company. It is structurally similar to and possesses a 1-beta-methyl group.
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| CAS Number: |
153832-46-3
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| Molecular Weight: |
475.515
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| DrugBank 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 <i>Escherichia coli</i>, <i>Clostridium clostridioforme</i>, <i>Eubacterium lentum</i>, <i>Peptostreptococcus</i> species, <i>Bacteroides fragilis</i>, <i>Bacteroides distasonis</i>, <i>Bacteroides ovatus</i>, <i>Bacteroides thetaiotaomicron</i>, or <i>Bacteroides uniformis</i>, (2) complicated skin and skin structure infections, including diabetic foot infections without osteomyelitis due to <i>Staphylococcus aureus</i> (methicillin susceptible isolates only), <i>Streptococcus agalactiae</i>, <i>Streptococcus pyogenes</i>, <i>Escherichia coli</i>, <i>Klebsiella pneumoniae</i>, <i>Proteus mirabilis</i>, <i>Bacteroides fragilis</i>, <i>Peptostreptococcus</i> species, <i>Porphyromonas asaccharolytica</i>, or <i>Prevotella bivia</i>, (3) community acquired pneumonia due to <i>Streptococcus pneumoniae</i> (penicillin susceptible isolates only) including cases with concurrent bacteremia, <i>Haemophilus influenzae</i> (beta-lactamase negative isolates only), or <i>Moraxella catarrhalis</i>, (4) complicated urinary tract infections including pyelonephritis due to <i>Escherichia coli</i>, including cases with concurrent bacteremia, or <i>Klebsiella pneumoniae</i>, (5) acute pelvic infections including postpartum endomyometritis, septic abortion and post surgical gynecologic infections due to <i>Streptococcus agalactiae</i>, <i>Escherichia coli</i>, <i>Bacteroides fragilis</i>, <i>Porphyromonas asaccharolytica</i>, <i>Peptostreptococcus</i> species, or <i>Prevotella bivia</i>.
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| DrugBank Pharmacology: |
Ertapenem has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria.
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| DrugBank MoA: |
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 <i>Escherichia coli</i>, 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.
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| Targets: |
Penicillin-binding protein 2 inhibitor; Penicillin-binding protein 2 inhibitor; Peptidoglycan synthase FtsI inhibitor; Peptidoglycan synthase FtsI inhibitor; D-alanyl-D-alanine carboxypeptidase DacB inhibitor; Penicillin-binding protein 1A inhibitor; Penicillin-binding protein 1B inhibitor; D-alanyl-D-alanine carboxypeptidase DacC inhibitor
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| Inclusion Criteria: |
Indication associated
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