Identification

Summary

Ertapenem is a carbapenem antibiotic used for the treatment of moderate to severe infections caused by susceptible bacteria.

Brand Names
Invanz
Generic Name
Ertapenem
DrugBank Accession Number
DB00303
Background

Ertapenem is a 1-β methyl-carbapenem that is structurally related to beta-lactam antibiotics.5 It was first authorized for use in the US in November 2001 and in Europe in April 2002.1 Shown to be effective against a wide range of Gram-positive and Gram-negative aerobic and anaerobic bacteria, ertapenem is used to treat various bacterial infections.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 475.515
Monoisotopic: 475.141320859
Chemical Formula
C22H25N3O7S
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

Pharmacology

Indication

Ertapenem is indicated to treat the following moderate to severe infections caused by susceptible bacteria in adult and pediatric patients (three months of age and older):5,6

  • Complicated intra-abdominal infections.5,6
  • Complicated skin and skin structure infections, including diabetic foot infections without osteomyelitis.5,6
  • Community-acquired pneumonia.5,6
  • Complicated urinary tract infections, including pyelonephritis.5
  • Acute pelvic infections, including postpartum endomyometritis, septic abortion and post-surgical gynecologic infections.5
  • Acute gynecological infections.6

Ertapenem is also used in adults for the prophylaxis of surgical site infection following elective colorectal surgery.5,6

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ertapenem is a carbapenem antibiotic with time-dependent bactericidal activity.3,4 Its optimal bactericidal activity is achieved when drug concentrations exceed the minimal inhibitory concentrations (MIC) for a specified portion of the dosing interval.2,3,4

It works against Gram-positive and Gram-negative aerobic and anaerobic bacteria. It is stable against hydrolysis by various beta-lactamases, including penicillinases, cephalosporinases, and extended-spectrum beta-lactamases, but not metallo-beta-lactamases.5,6

Mechanism of action

Ertapenem exhibits a bactericidal mode of action.2 It works by binding to and inhibiting bacterial penicillin-binding proteins (PBPs).5 In Escherichia coli, it has a strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preferential binding to PBPs 2 and 3.5 Upon binding to PBPs, ertapenem inhibits bacterial cell wall synthesis by interfering with the lengthening and strengthening of the peptidoglycan portion of the cell wall, thereby inhibiting cell wall synthesis.3

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1B
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 2
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
APenicillin-binding protein 2
inhibitor
Escherichia coli (strain K12)
APeptidoglycan synthase FtsI
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
APeptidoglycan synthase FtsI
inhibitor
Escherichia coli (strain K12)
AD-alanyl-D-alanine carboxypeptidase DacB
inhibitor
Escherichia coli (strain K12)
AD-alanyl-D-alanine carboxypeptidase DacC
inhibitor
Escherichia coli (strain K12)
Absorption

Ertapenem is almost completely absorbed following intramuscular administration, with a mean bioavailability of approximately 90%.5

Plasma concentrations of ertapenem are similar whether given intramuscularly or intravenously; however, the peak concentrations are lower when given via the intramuscular route. The time to reach the Cmax (Tmax) is slightly longer when given via the intramuscular route.1 Following daily intramuscular administration of one gram of ertapenem, the Tmax was approximately 2.3 hours.5 In healthy young adults who received a single 30-minute intravenous infusion of one gram of ertapenem, the Cmax was 155 µG/mL at 0.5 hours postdose.6

Volume of distribution

The apparent volume of distribution at steady state (Vss) of ertapenem is approximately 0.12 L/kg in adults, 0.2 L/kg in children three months to 12 years of age, and 0.16 L/kg in adolescents 13 to 17 years of age. Ertapenem does not accumulate.5

Protein binding

Ertapenem binds to plasma proteins in a concentration-dependent manner. It is highly bound to human plasma proteins, primarily to albumin.5 Protein binding is saturable at higher doses, at which the unbound fraction of the drug increases disproportionately.3 In healthy young adults, the protein binding of ertapenem decreased as drug plasma concentrations increased. At an approximate plasma concentration of <100 micrograms (mcg)/mL, ertapenem was 95% bound, and this percentage dropped to 85% when the plasma concentration increased to 300 mcg/mL.5

Metabolism

In healthy young adults, unchanged ertapenem accounted for most plasma radioactivity.5 The major metabolite of ertapenem is the ring-opened derivative formed by dehydropeptidase I-mediated hydrolysis of the beta-lactam ring.4,6 This metabolite is pharmacologically inactive.5 Dehydropeptidase I (DHP-I) is found predominantly in the kidneys.1 Hepatic metabolism is negligible.3

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Route of elimination

Ertapenem predominantly undergoes renal elimination, where it undergoes glomerular filtration and net tubular secretion.1 In healthy young adults who received one gram of IV radiolabeled ertapenem, approximately 80% of the radioactivity was recovered in urine and 10% of the radioactivity was recovered in feces. The mean percentage of the administered dose excreted in urine was 17.4% during 0-2 hours postdose, 5.4% during 4-6 hours postdose, and 2.4% during 12-24 hours postdose.5

Of the 80% radioactivity in urine, about 38% accounted for unchanged ertapenem and 37% accounted for its ring-opened metabolite.5

Half-life

The mean plasma half-life was approximately four hours in healthy young adults and adolescents and approximately 2.5 hours in children three to 12 years of age.5 The long half-life of ertapenem can be explained by its high protein binding.2

Clearance

The mean plasma clearance in healthy young adults was approximately 1.8 L/hour.5 The mean renal clearance of intact ertapenem was 12.8 mL/min compared with a total clearance of 28.4 mL/min.1

Adverse Effects
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Toxicity

The oral median lethal dose (LD50) in mouse is >500 mg/kg.7

Intravenous administration of ertapenem at a dose of 2 g over 30 min or 3 g over 1-2 hours in healthy adults resulted in increased incidence of nausea. In clinical trials in adults, inadvertent administration of three 1 g doses of ertapenem in a 24 hour period resulted in diarrhea and transient dizziness in one patient. As there is no known antidote for ertapenem overdose, the drug should be discontinued with the initiation of general supportive treatment until renal elimination takes place. Ertapenem can be removed by hemodialysis to some extent: the plasma clearance of the total fraction of ertapenem was increased by 30% in subjects with end-stage renal disease when hemodialysis was performed immediately following administration. However, no information is available on the use of hemodialysis to treat ertapenem overdosage.5

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirErtapenem may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ertapenem which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ertapenem which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Ertapenem is combined with Acenocoumarol.
AcetaminophenErtapenem may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Ertapenem which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ertapenem which could result in a higher serum level.
AclidiniumErtapenem may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineErtapenem may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Ertapenem which could result in a higher serum level.
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ertapenem sodium2T90KE67L0153773-82-1ZXNAQFZBWUNWJM-HRXMHBOMSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ErtapenemInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousPar Pharmaceutical Inc.2018-11-01Not applicableUS flag
Ertapenem for InjectionPowder, for solution1 g / vialIntramuscular; IntravenousFresenius Kabi2021-06-07Not applicableCanada flag
Ertapenem for InjectionPowder, for solution1 g / vialIntramuscular; IntravenousAuro Pharma Inc2021-10-08Not applicableCanada flag
Ertapenem for InjectionPowder, for solution1 g / vialIntramuscular; IntravenousHikma Canada LimitedNot applicableNot applicableCanada flag
Ertapenem for InjectionPowder, for solution1 g / vialIntramuscular; IntravenousDr Reddy's Laboratories Ltd2021-01-27Not applicableCanada flag
Ertapenem for InjectionPowder, for solution1 g / vialIntramuscular; IntravenousJuno Pharmaceuticals Corp.2020-02-10Not applicableCanada flag
Ertapenem SunInjection, powder, for solution1 gIntravenousSun Pharmaceutical Industries (Europe) B.V.2022-12-02Not applicableEU flag
Ertapenem SunInjection, powder, for solution1 gIntravenousSun Pharmaceutical Industries (Europe) B.V.2022-12-02Not applicableEU flag
InvanzInjection, powder, for solution1 gIntravenousMerck Sharp & Dohme B.V.2016-09-08Not applicableEU flag
InvanzInjection, powder, lyophilized, for solution1 g/1IntravenousMerck Sharp & Dohme Llc2001-11-212018-07-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ErtapenemInjection1 g/20mLIntramuscular; IntravenousApotex Corp2019-04-02Not applicableUS flag
ErtapenemInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousHospira, Inc.2020-10-19Not applicableUS flag
ErtapenemInjection1 g/20mLIntramuscular; IntravenousSavior Lifetec Corporation2019-03-19Not applicableUS flag
ErtapenemInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousWG Critical Care, LLC2020-01-07Not applicableUS flag
ErtapenemInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousFosun Pharma USA Inc2021-11-01Not applicableUS flag
ErtapenemInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousFresenius Kabi USA, LLC2019-10-10Not applicableUS flag
ErtapenemInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousGland Pharma Limited2021-03-26Not applicableUS flag
ErtapenemInjection1 g/1Intramuscular; IntravenousAuroMedics Pharma LLC2018-06-25Not applicableUS flag
ErtapenemInjection1 g/20mLIntramuscular; IntravenousBluePoint Laboratories2019-08-29Not applicableUS flag
Ertapenem SodiumInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousHikma Pharmaceuticals USA, Inc.2021-08-02Not applicableUS flag

Categories

ATC Codes
J01DH03 — Ertapenem
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Thienamycins
Alternative Parents
Acylaminobenzoic acid and derivatives / Proline and derivatives / Alpha amino acid amides / Anilides / Benzoic acids / Pyrroline carboxylic acids / Pyrrolidinecarboxamides / Benzoyl derivatives / N-arylamides / Azepines
show 16 more
Substituents
Acylaminobenzoic acid or derivatives / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Anilide / Aromatic heteropolycyclic compound / Azacycle
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolidinecarboxamide, carbapenemcarboxylic acid (CHEBI:404903)
Affected organisms
  • Enteric bacteria and other eubacteria
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Streptococcus agalactiae
  • Haemophilus influenzae
  • Escherichia coli
  • Staphylococcus aureus
  • Moraxella catarrhalis
  • Proteus mirabilis
  • Bacteroides fragilis
  • Peptostreptococcus
  • Klebsiella pneumoniae
  • Bacteroides thetaiotaomicron
  • Bacteroides ovatus
  • Bacteroides uniformis
  • Parabacteroides distasonis
  • Eubacterium spp.
  • Clostridium clostridioforme
  • Prevotella bivia
  • Porphyromonas asaccharolytica

Chemical Identifiers

UNII
G32F6EID2H
CAS number
153832-46-3
InChI Key
JUZNIMUFDBIJCM-ANEDZVCMSA-N
InChI
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
IUPAC 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
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

References

Synthesis Reference

Ying Shi, Kun Li, Zan Xie, Xuebin Zhao, Jian Lv, Xiuqin Yu, "INTERMEDIATE OF ERTAPENEM, A COMPOSITION COMPRISING THE SAME AND PREPARATION METHODS THEREOF." U.S. Patent US20120095209, issued April 19, 2012.

US20120095209
General References
  1. 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. [Article]
  2. Odenholt I: Ertapenem: a new carbapenem. Expert Opin Investig Drugs. 2001 Jun;10(6):1157-66. [Article]
  3. Congeni BL: Ertapenem. Expert Opin Pharmacother. 2010 Mar;11(4):669-72. doi: 10.1517/14656561003631397. [Article]
  4. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  5. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
  6. EMA Approved Drug Products: Ertapenem SUN (ertapenem) Intravenous Infusion [Link]
  7. Merck: Ertapenem MSDS [Link]
Human Metabolome Database
HMDB0014448
KEGG Drug
D07908
PubChem Compound
150610
PubChem Substance
46506508
ChemSpider
132758
RxNav
325642
ChEBI
404903
ChEMBL
CHEMBL1359
ZINC
ZINC000003918453
Therapeutic Targets Database
DAP000431
PharmGKB
PA164777032
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ertapenem

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAcute Renal Failure (ARF)1
4CompletedNot AvailableContinuous ambulatory peritoneal dialysis therapy / End Stage Renal Disease (ESRD)1
4CompletedNot AvailableHealthy Subjects (HS)1
4CompletedNot AvailableInfection1
4CompletedPreventionBenign Prostatic Hyperplasia (BPH) Requiring Surgical Resection1
4CompletedTreatmentBurn Patients1
4CompletedTreatmentComplicated Intra-Abdominal Infections (cIAIs)1
4CompletedTreatmentDiverticulosis, Colonic / Neoplasms, Colonic / Rectal Neoplasms1
4CompletedTreatmentIntraabdominal Infections1
4CompletedTreatmentLiver Abscess, Pyogenic1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
  • Merck & Co.
Dosage Forms
FormRouteStrength
InjectionIntramuscular; Intravenous1 g/20mL
InjectionIntramuscular; Intravenous1 g/1
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionParenteral
Injection, powder, for solutionIntravenous1 g/vial
Injection, powder, for solution
Injection, powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous drip1 G/VIAL
Injection, powder, lyophilized, for solutionIntravenous1 g
PowderNot applicable1 kg/1kg
Injection, powder, for solution1213 mg
Injection, powder, for solutionIntravenous1 g
Injection, powder, for solutionIntravenous; Parenteral1 G
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Powder, for solutionIntramuscular; Intravenous1 g / vial
Injection, powder, for solutionIntramuscular; Intravenous1 g
InjectionIntramuscular; Intravenous1 g
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous1 g
Prices
Unit descriptionCostUnit
Invanz 1 gm add-vantage vial72.85USD vial
Invanz 1 gm vial69.4USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5652233No1997-07-292013-02-02US flag
CA2106370No2003-11-252013-02-02Canada flag
US5478820Yes1995-12-262016-05-21US flag
US5952323Yes1999-09-142017-11-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)230-234https://www.fishersci.com/store/msds?partNumber=AC460640010&productDescription=ERTAPENEM+SODIUM%2C+85%25+1GR&vendorId=VN00032119&countryCode=US&language=en
logP0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.286 mg/mLALOGPS
logP-0.2ALOGPS
logP-3.2Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.22Chemaxon
pKa (Strongest Basic)9.03Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area156.27 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity121.8 m3·mol-1Chemaxon
Polarizability48.77 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5982
Blood Brain Barrier-0.9811
Caco-2 permeable-0.7052
P-glycoprotein substrateSubstrate0.7716
P-glycoprotein inhibitor INon-inhibitor0.917
P-glycoprotein inhibitor IINon-inhibitor0.9955
Renal organic cation transporterNon-inhibitor0.9253
CYP450 2C9 substrateNon-substrate0.7891
CYP450 2D6 substrateNon-substrate0.8229
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8677
CYP450 2C9 inhibitorNon-inhibitor0.867
CYP450 2D6 inhibitorNon-inhibitor0.8964
CYP450 2C19 inhibitorNon-inhibitor0.8511
CYP450 3A4 inhibitorNon-inhibitor0.9658
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9695
Ames testNon AMES toxic0.6766
CarcinogenicityNon-carcinogens0.8052
BiodegradationNot ready biodegradable0.9821
Rat acute toxicity2.0803 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9947
hERG inhibition (predictor II)Non-inhibitor0.8848
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
mrcA
Uniprot ID
P02918
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
93635.545 Da
References
  1. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  2. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  3. Congeni BL: Ertapenem. Expert Opin Pharmacother. 2010 Mar;11(4):669-72. doi: 10.1517/14656561003631397. [Article]
  4. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
mrcB
Uniprot ID
P02919
Uniprot Name
Penicillin-binding protein 1B
Molecular Weight
94291.875 Da
References
  1. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  2. Congeni BL: Ertapenem. Expert Opin Pharmacother. 2010 Mar;11(4):669-72. doi: 10.1517/14656561003631397. [Article]
  3. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  4. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Penicillin binding
Specific Function
Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. Its synthesize cross-linked peptidoglycan from the lipid intermediates (By similarity).
Gene Name
mrdA
Uniprot ID
P44469
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
73812.47 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Odenholt I: Ertapenem: a new carbapenem. Expert Opin Investig Drugs. 2001 Jun;10(6):1157-66. [Article]
  4. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  5. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. It synthesizes cross-linked peptidoglycan from lipid intermediates.
Gene Name
mrdA
Uniprot ID
P0AD65
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
70856.1 Da
References
  1. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  2. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  3. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum. Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors.
Gene Name
ftsI
Uniprot ID
P45059
Uniprot Name
Peptidoglycan synthase FtsI
Molecular Weight
67165.845 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  4. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  5. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan fr...
Gene Name
ftsI
Uniprot ID
P0AD68
Uniprot Name
Peptidoglycan synthase FtsI
Molecular Weight
63876.925 Da
References
  1. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  2. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  3. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Gene Name
dacB
Uniprot ID
P24228
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacB
Molecular Weight
51797.85 Da
References
  1. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  2. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  3. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name
dacC
Uniprot ID
P08506
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacC
Molecular Weight
43608.595 Da
References
  1. Kohler J, Dorso KL, Young K, Hammond GG, Rosen H, Kropp H, Silver LL: In vitro activities of the potent, broad-spectrum carbapenem MK-0826 (L-749,345) against broad-spectrum beta-lactamase-and extended-spectrum beta-lactamase-producing Klebsiella pneumoniae and Escherichia coli clinical isolates. Antimicrob Agents Chemother. 1999 May;43(5):1170-6. [Article]
  2. Curran M, Simpson D, Perry C: Ertapenem: a review of its use in the management of bacterial infections. Drugs. 2003;63(17):1855-78. doi: 10.2165/00003495-200363170-00006. [Article]
  3. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Zinc ion binding
Specific Function
Hydrolyzes a wide range of dipeptides. Implicated in the renal metabolism of glutathione and its conjugates. Converts leukotriene D4 to leukotriene E4; it may play an important role in the regulati...
Gene Name
DPEP1
Uniprot ID
P16444
Uniprot Name
Dipeptidase 1
Molecular Weight
45673.48 Da
References
  1. 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. [Article]
  2. EMA Approved Drug Products: Ertapenem SUN (ertapenem) Intravenous Infusion [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]

Drug created at June 13, 2005 13:24 / Updated at February 04, 2023 13:36