Ertapenem
Explore a selection of our essential drug information below, or:
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Severe community-acquired pneumonia (scap) •••••••••••• Prophylaxis of Surgical site infections •••••••••••• ••••• Treatment of Acute gynaecological infection •••••••••••• Treatment of Acute, moderate pelvic infections caused by susceptible bacteria •••••••••••• Treatment of Acute, severe susceptible bacteria pelvic infections •••••••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
Target Actions Organism APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) APenicillin-binding protein 2 inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) APenicillin-binding protein 2 inhibitorEscherichia coli (strain K12) APeptidoglycan synthase FtsI inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) AD-alanyl-D-alanine carboxypeptidase DacB inhibitorEscherichia coli (strain K12) AD-alanyl-D-alanine carboxypeptidase DacC inhibitorEscherichia 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
Hover over products below to view reaction partners
- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Ertapenem may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Ertapenem which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Ertapenem which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Ertapenem is combined with Acenocoumarol. Acetaminophen Ertapenem may decrease the excretion rate of Acetaminophen which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Ertapenem sodium 2T90KE67L0 153773-82-1 ZXNAQFZBWUNWJM-HRXMHBOMSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ertapenem Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous ENDO USA, Inc. 2018-11-01 Not applicable US Ertapenem for Injection Powder, for solution 1 g / vial Intramuscular; Intravenous Eugia Pharma (Malta) Limited 2024-07-23 Not applicable Canada Ertapenem for Injection Powder, for solution 1 g / vial Intramuscular; Intravenous Fresenius Kabi Italia S.R.L. 2021-06-07 Not applicable Canada Ertapenem for Injection Powder, for solution 1 g / vial Intramuscular; Intravenous Mantra Pharma Inc Not applicable Not applicable Canada Ertapenem for Injection Powder, for solution 1 g / vial Intramuscular; Intravenous Dr. Reddy's Laboratories Limited 2021-01-27 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ertapenem Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous Hospira, Inc. 2020-10-19 Not applicable US Ertapenem Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous Fresenius Kabi Italia S.R.L. 2019-10-10 Not applicable US Ertapenem Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous Fosun Pharma USA Inc 2021-11-01 Not applicable US Ertapenem Injection 1 g/1 Intramuscular; Intravenous Eugia US LLC 2018-06-25 Not applicable US Ertapenem Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous WG Critical Care, LLC 2020-01-07 Not applicable US
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
- 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]
- Odenholt I: Ertapenem: a new carbapenem. Expert Opin Investig Drugs. 2001 Jun;10(6):1157-66. [Article]
- Congeni BL: Ertapenem. Expert Opin Pharmacother. 2010 Mar;11(4):669-72. doi: 10.1517/14656561003631397. [Article]
- 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]
- FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
- EMA Approved Drug Products: Ertapenem SUN (ertapenem) Intravenous Infusion [Link]
- Merck: Ertapenem MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0014448
- KEGG Drug
- D07908
- PubChem Compound
- 150610
- PubChem Substance
- 46506508
- ChemSpider
- 132758
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Treatment Appendicitis Acute 2 somestatus stop reason just information to hide Not Available Completed Not Available Bacteremia / Bacterial Infections 1 somestatus stop reason just information to hide Not Available Completed Treatment Appendicitis 1 somestatus stop reason just information to hide Not Available Completed Treatment Perforated Appendicitis 1 somestatus stop reason just information to hide Not Available Enrolling by Invitation Other Appendicitis Acute 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Merck and co inc
- Packagers
- Merck & Co.
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intramuscular; Intravenous 100000 g Injection Intramuscular; Intravenous 1 g/1 Injection Intramuscular; Intravenous 1 g/20mL Injection, powder, lyophilized, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution 1 G Injection, powder, for solution Parenteral 1 g Injection, powder, for solution Intravenous 1 g/vial Injection, powder, for solution Injection, powder, for solution Intravenous Injection, powder, lyophilized, for solution Intravenous drip 1 G/VIAL Injection, powder, lyophilized, for solution Intravenous 1 g Powder Not applicable 1 kg/1kg Injection, powder, for solution Intravenous 1 g Injection, powder, lyophilized, for solution Intramuscular; Intravenous 1 g Solution Intravenous 1.292 g Injection, powder, for solution 1213 mg Injection, powder, for solution Intravenous; Parenteral 1 G Injection, powder, lyophilized, for solution Intravenous 1 g/1 Powder, for solution Intramuscular; Intravenous 1 g / vial Solution Parenteral 1.000 g Injection, powder, for solution Intramuscular; Intravenous 1 g Injection Intramuscular; Intravenous 1 g Solution Intravenous 1.046 g - Prices
Unit description Cost Unit Invanz 1 gm add-vantage vial 72.85USD vial Invanz 1 gm vial 69.4USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5652233 No 1997-07-29 2013-02-02 US CA2106370 No 2003-11-25 2013-02-02 Canada US5478820 Yes 1995-12-26 2016-05-21 US US5952323 Yes 1999-09-14 2017-11-15 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 230-234 https://www.fishersci.com/store/msds?partNumber=AC460640010&productDescription=ERTAPENEM+SODIUM%2C+85%25+1GR&vendorId=VN00032119&countryCode=US&language=en logP 0.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.286 mg/mL ALOGPS logP -0.2 ALOGPS logP -3.2 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 3.22 Chemaxon pKa (Strongest Basic) 9.03 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 156.27 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 121.8 m3·mol-1 Chemaxon Polarizability 48.77 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5982 Blood Brain Barrier - 0.9811 Caco-2 permeable - 0.7052 P-glycoprotein substrate Substrate 0.7716 P-glycoprotein inhibitor I Non-inhibitor 0.917 P-glycoprotein inhibitor II Non-inhibitor 0.9955 Renal organic cation transporter Non-inhibitor 0.9253 CYP450 2C9 substrate Non-substrate 0.7891 CYP450 2D6 substrate Non-substrate 0.8229 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.8677 CYP450 2C9 inhibitor Non-inhibitor 0.867 CYP450 2D6 inhibitor Non-inhibitor 0.8964 CYP450 2C19 inhibitor Non-inhibitor 0.8511 CYP450 3A4 inhibitor Non-inhibitor 0.9658 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9695 Ames test Non AMES toxic 0.6766 Carcinogenicity Non-carcinogens 0.8052 Biodegradation Not ready biodegradable 0.9821 Rat acute toxicity 2.0803 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9947 hERG inhibition (predictor II) Non-inhibitor 0.8848
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-052s-9534600000-4519573496014739b64d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-056r-0000900000-2864d6cec3ebe4d584be Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00e9-0000900000-e05b7fb8579fdad113b8 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0010900000-b8450b0084c0db25d13a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0230-0222900000-77ddaebc83b9be5ac3c5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-054o-1335900000-8a2da621277c2d0cde89 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-1360900000-107d11f99261615da940 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 213.1429424 predictedDarkChem Lite v0.1.0 [M-H]- 215.4829424 predictedDarkChem Lite v0.1.0 [M-H]- 208.22102 predictedDeepCCS 1.0 (2019) [M+H]+ 215.5979424 predictedDarkChem Lite v0.1.0 [M+H]+ 216.2287424 predictedDarkChem Lite v0.1.0 [M+H]+ 210.11644 predictedDeepCCS 1.0 (2019) [M+Na]+ 215.3086424 predictedDarkChem Lite v0.1.0 [M+Na]+ 214.6970424 predictedDarkChem Lite v0.1.0 [M+Na]+ 215.95619 predictedDeepCCS 1.0 (2019)
Targets
- 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
- 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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
- Specific Function
- penicillin binding
- Gene Name
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- 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]
- 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]
- Congeni BL: Ertapenem. Expert Opin Pharmacother. 2010 Mar;11(4):669-72. doi: 10.1517/14656561003631397. [Article]
- 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
- 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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
- Specific Function
- penicillin binding
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- 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]
- Congeni BL: Ertapenem. Expert Opin Pharmacother. 2010 Mar;11(4):669-72. doi: 10.1517/14656561003631397. [Article]
- 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]
- 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
- Catalyzes cross-linking of the peptidoglycan cell wall.
- Specific Function
- penicillin binding
- Gene Name
- mrdA
- Uniprot ID
- P44469
- Uniprot Name
- Penicillin-binding protein 2
- Molecular Weight
- 73812.47 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- Odenholt I: Ertapenem: a new carbapenem. Expert Opin Investig Drugs. 2001 Jun;10(6):1157-66. [Article]
- 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]
- 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
- Catalyzes cross-linking of the peptidoglycan cell wall (PubMed:3009484). Responsible for the determination of the rod shape of the cell (PubMed:1103132). Is probably required for lateral peptidoglycan synthesis and maintenance of the correct diameter during lateral and centripetal growth (PubMed:12519203).
- Specific Function
- penicillin binding
- Gene Name
- mrdA
- Uniprot ID
- P0AD65
- Uniprot Name
- Penicillin-binding protein 2
- Molecular Weight
- 70856.1 Da
References
- 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]
- 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]
- 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
- Catalyzes cross-linking of the peptidoglycan cell wall at the division septum.
- Specific Function
- penicillin binding
- Gene Name
- ftsI
- Uniprot ID
- P45059
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 67165.845 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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]
- 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
- Essential cell division protein that catalyzes cross-linking of the peptidoglycan cell wall at the division septum (PubMed:1103132, PubMed:3531167, PubMed:6450748, PubMed:7030331, PubMed:9614966). Required for localization of FtsN (PubMed:9282742).
- Specific Function
- penicillin binding
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- 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]
- 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]
- 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
- Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
- Specific Function
- carboxypeptidase activity
- Gene Name
- dacB
- Uniprot ID
- P24228
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacB
- Molecular Weight
- 51797.85 Da
References
- 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]
- 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]
- 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
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- carboxypeptidase activity
- Gene Name
- dacC
- Uniprot ID
- P08506
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacC
- Molecular Weight
- 43608.595 Da
References
- 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]
- 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]
- 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
- Hydrolyzes a wide range of dipeptides including the conversion of leukotriene D4 to leukotriene E4 (PubMed:2303490, PubMed:31442408, PubMed:32325220, PubMed:6334084). Hydrolyzes cystinyl-bis-glycine (cys-bis-gly) formed during glutathione degradation (PubMed:32325220). Possesses also beta lactamase activity and can hydrolyze the beta-lactam antibiotic imipenem (PubMed:32325220, PubMed:6334084)
- Specific Function
- beta-lactamase activity
- Gene Name
- DPEP1
- Uniprot ID
- P16444
- Uniprot Name
- Dipeptidase 1
- Molecular Weight
- 45673.48 Da
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- FDA Approved Drug Products: INVANZ (ertapenem) injection, for intravenous or intramuscular use [Link]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 17:59