Identification

Name
Ertapenem
Accession Number
DB00303  (APRD00952)
Type
Small Molecule
Groups
Approved, Investigational
Description

Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz. It is structurally very similar to meropenem in that it possess a 1-beta-methyl group.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Ertapenem sodium2T90KE67L0153773-82-1ZXNAQFZBWUNWJM-HRXMHBOMSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ErtapenemInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousPar Pharmaceutical Inc.2018-07-26Not applicableUs
InvanzInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousMerck Sharp & Dohme Corp.2001-11-21Not applicableUs
InvanzPowder, for solution1 gIntramuscular; IntravenousMerck Ltd.2003-08-27Not applicableCanada
InvanzInjection, powder, for solution1 gIntravenousMerck Sharp & Dohme B.V.2002-04-18Not applicableEu
InvanzInjection, powder, lyophilized, for solution1 g/1IntravenousMerck Sharp & Dohme Corp.2001-11-212018-07-31Us
InvanzInjection, powder, for solution1 gIntravenousMerck Sharp & Dohme B.V.2002-04-18Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ErtapenemInjection1 g/1Intramuscular; IntravenousAuro Medics Pharma Llc2018-06-25Not applicableUs
Categories
UNII
G32F6EID2H
CAS number
153832-46-3
Weight
Average: 475.515
Monoisotopic: 475.141320859
Chemical Formula
C22H25N3O7S
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

Pharmacology

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.

Associated Conditions
Pharmacodynamics

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

Mechanism 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.

TargetActionsOrganism
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)
APenicillin-binding protein 1A
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1B
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. The bioavailability of a 1 g intramuscular dose approximated 92% in 26 healthy subjects [77% male; median (range) age, 29 (22–41) years]. Plasma concentrations of total ertapenem were similar whether given intramuscularly or intravenously.

Volume of distribution
  • 0.12 liter/kg [adults]
  • 0.2 liter/kg [pediatric, 3 months to 12 years]
  • 0.16 liter/kg [pediatric patients 13 to 17 years]
Protein binding

Ertapenem is highly bound to human plasma proteins, primarily albumin, in a concentration-dependent manner. The protein binding of ertapenem decreases as plasma concentrations increase. At a plasma concentration of <100 µg/mL, approximately 95% of ertapenem is protein bound. Protein binding of ertapenem decreases to approximately 85% at an approximate plasma concentration of 300 µg/mL.

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]

Route of elimination

Of the 80% recovered in urine, approximately 38% is excreted as unchanged drug and approximately 37% as the ring-opened metabolite.

Half life

The mean plasma half-life is approximately 4 hours.

Clearance
  • 1.8 L/h
Toxicity
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Ertapenem is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Ertapenem is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Ertapenem is combined with 4-hydroxycoumarin.
AbacavirErtapenem may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Ertapenem 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.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ertapenem which could result in a higher serum level.
Food Interactions
Not Available

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. [PubMed:15150180]
External Links
Human Metabolome Database
HMDB0014448
KEGG Drug
D07908
PubChem Compound
150610
PubChem Substance
46506508
ChemSpider
132758
ChEBI
404903
ChEMBL
CHEMBL1359
Therapeutic Targets Database
DAP000431
PharmGKB
PA164777032
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ertapenem
ATC Codes
J01DH03 — Ertapenem
AHFS Codes
  • 08:12.07.08 — Carbapenems
FDA label
Download (140 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedHealth Services ResearchHealthy Volunteers1
1TerminatedTreatmentEndometritis1
2CompletedOtherEnd Stage Renal Disease (ESRD)1
2CompletedOtherPK of Ertapenem in TB Patients1
2CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
2CompletedTreatmentComplicated Intra-Abdominal Infections1
2Not Yet RecruitingTreatmentAppendicitis Acute1
2RecruitingTreatmentAcute Pyelonephritis / Infection Due to Escherichia Coli1
2, 3Active Not RecruitingTreatmentAnti-Infective Agents, Urinary / Escherichia Coli Infections / Klebsiella Infections / Transplantation, Kidney / Urinary Tract Infections (UTIs)1
2, 3CompletedPreventionSurgical Site Infections1
3CompletedPreventionInfection NOS / Surgical Site Infections1
3CompletedTreatmentBacterial Infections / Diabetic Foot / Osteomyelitis1
3CompletedTreatmentComplicated Intra-Abdominal Infections1
3CompletedTreatmentComplicated Urinary Tract Infections1
3CompletedTreatmentInfection NOS1
3CompletedTreatmentInfection; Diabetic Foot1
3CompletedTreatmentIntraabdominal Infections1
3CompletedTreatmentUrinary Tract Infections (UTIs)2
3RecruitingTreatmentAntibiotic Resistant Infection / Complicated skin infection bacterial / Complicated Urinary Tract Infections / Urinary Tract Infections (UTIs)1
3RecruitingTreatmentAntibiotic Resistant Infection / Complicated skin infection bacterial / Intra Abdominal Infections1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentGonorrhea1
3RecruitingTreatmentUrinary Tract Infections (UTIs)1
3TerminatedTreatmentUrinary Tract Infections (UTIs)1
3Unknown StatusTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedNot AvailableAcute Renal Failure (ARF)1
4CompletedNot AvailableContinuous ambulatory peritoneal dialysis therapy / End Stage Renal Disease (ESRD)1
4CompletedNot AvailableHealthy Volunteers1
4CompletedNot AvailableInfection NOS1
4CompletedPreventionBenign Prostatic Hyperplasia (BPH) Requiring Surgical Resection1
4CompletedTreatmentBurn Patients1
4CompletedTreatmentColonic Neoplasms / Diverticulosis, Colonic / Rectal Neoplasms1
4CompletedTreatmentIntra-Abdominal Infections1
4CompletedTreatmentLiver Abscess, Pyogenic1
4TerminatedTreatmentTo Assess the Tissular and Plasma Kinetics of Ertapenem1
4Unknown StatusNot AvailableAllergies / IgE-Mediated Hypersensitivity1
4Unknown StatusEducational/Counseling/TrainingAcute Disease / Diverticulitis, Colonic1
4Unknown StatusTreatmentAcute Appendicitis Without Peritonitis1
4Unknown StatusTreatmentDrug Safety1
Not AvailableActive Not RecruitingTreatmentAppendicitis Acute1
Not AvailableCompletedTreatmentPerforated Appendicitis1
Not AvailableEnrolling by InvitationTreatmentAppendicitis Acute1
Not AvailableRecruitingTreatmentAppendicitis Acute1
Not AvailableUnknown StatusNot AvailableUrinary Tract Infections (UTIs)1
Not AvailableWithdrawnTreatmentAmputations1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
  • Merck & Co.
Dosage forms
FormRouteStrength
InjectionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionIntravenous1 g
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Powder, 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)
US5652233No1997-07-292013-02-02Us
CA2106370No2003-11-252013-02-02Canada
US5478820Yes1995-12-262016-05-21Us
US5952323Yes1999-09-142017-11-15Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySoluble as sodium saltNot Available
logP0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.286 mg/mLALOGPS
logP-0.2ALOGPS
logP-3.2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
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

Taxonomy

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
Thienamycin / Acylaminobenzoic acid or derivatives / Proline or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Benzoic acid or derivatives / Benzoic acid / Anilide / Benzoyl / Pyrrolidine carboxylic acid or derivatives
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolidinecarboxamide, carbapenemcarboxylic acid (CHEBI:404903)

Targets

Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Odenholt I: Ertapenem: a new carbapenem. Expert Opin Investig Drugs. 2001 Jun;10(6):1157-66. [PubMed:11772242]
  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. [PubMed:10223931]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:10223931]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10223931]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:10223931]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:10223931]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:10223931]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:10223931]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
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. [PubMed:10223931]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2018 11:04