Identification

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Name
Imipenem
Accession Number
DB01598
Type
Small Molecule
Groups
Approved
Description

Imipenem is a semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains.Label It is stable to many beta-lactamases. Similar compounds include meropenem, known for having greater activity against Gram negative bacteria, and the newer [ertapenam] which exhibits a longer half-life due to increased binding to plasma proteins.10 Imipenem is commonly used in combination with cilastatin and is now available in a triple-drug product with cilastatin and relebactam which was recently approved by the FDA. Imipenem was first approved by the FDA in November 1985 as the combination product Primaxin marketed by Merck & Co.14

Structure
Thumb
Synonyms
  • (5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
  • (5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure
  • Imipenem
  • Imipenem anhydrous
  • Imipenemum
  • N-formimidoyl thienamycin
  • N-formimidoylthienamycin
Product Ingredients
IngredientUNIICASInChI Key
Imipenem monohydrate71OTZ9ZE0A74431-23-5GSOSVVULSKVSLQ-JJVRHELESA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Imipenem and CilastatinImipenem monohydrate (250 mg/20mL) + Cilastatin sodium (250 mg/20mL)Injection, powder, for solutionIntravenousFresenius Kabi USA, LLC2012-01-03Not applicableUs
Imipenem and CilastatinImipenem monohydrate (500 mg/100mL) + Cilastatin sodium (500 mg/100mL)Injection, powder, for solutionIntravenousHospira, Inc.2011-11-16Not applicableUs
Imipenem and CilastatinImipenem monohydrate (250 mg/100mL) + Cilastatin sodium (250 mg/100mL)Injection, powder, for solutionIntravenousHospira, Inc.2011-11-16Not applicableUs
Imipenem and CilastatinImipenem monohydrate (500 mg/1) + Cilastatin sodium (500 mg/1)Injection, powder, for solutionIntravenousCardinal Health2012-01-032018-07-09Us
Imipenem and CilastatinImipenem monohydrate (500 mg/20mL) + Cilastatin sodium (500 mg/20mL)Injection, powder, for solutionIntravenousFresenius Kabi USA, LLC2012-01-03Not applicableUs
Imipenem and Cilastatin for InjectionImipenem (500 mg) + Cilastatin (500 mg)Powder, for solutionIntravenousPfizer Canada Ulc2011-05-022019-06-28Canada
Imipenem and Cilastatin for InjectionImipenem (250 mg) + Cilastatin (250 mg)Powder, for solutionIntravenousPfizer Canada UlcNot applicableNot applicableCanada
Imipenem and Cilastatin for Injection USPImipenem (500 mg) + Cilastatin (500 mg)Powder, for solutionIntravenousSandoz Canada Incorporated2010-12-21Not applicableCanada
Imipenem and Cilastatin for Injection USPImipenem (250 mg) + Cilastatin (250 mg)Powder, for solutionIntravenousSandoz Canada Incorporated2010-12-21Not applicableCanada
Imipenem and Cilastatin for Injection, USPImipenem (500 mg) + Cilastatin (500 mg)Powder, for solutionIntravenousMethapharm, Inc.Not applicableNot applicableCanada
International/Other Brands
Tienamycin
Categories
UNII
Q20IM7HE75
CAS number
64221-86-9
Weight
Average: 299.346
Monoisotopic: 299.093976737
Chemical Formula
C12H17N3O4S
InChI Key
ZSKVGTPCRGIANV-ZXFLCMHBSA-N
InChI
InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
IUPAC Name
(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
SMILES
[H][C@]12CC(SCC\N=C\N)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

Pharmacology

Indication

Imipenem is indicated, in combination with cilastatin with or without relebactam, for the treatment of bacterial infections including respiratory, skin, bone, gynecologic, urinary tract, and intra-abdominal as well as septicemia and endocarditis.12,13

Associated Conditions
Pharmacodynamics

Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems.12,13 Imipenem is active against aerobic and anaerobic Gram positive as well as Gram negative bacteria including Pseudomonas aeruginosa and the Enterococcus. It exerts a bactericidal effects by disrupting cell wall synthesis.

Mechanism of action

Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria.12,13 This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to penicillin-binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b.9 This inhibition of PBPs prevents the bacterial cell from adding to the peptidoglycan polymer which forms the bacterial cell wall eventually leading to cell death.11

TargetActionsOrganism
APenicillin-binding protein 2
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1B
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1A
inhibitor
Escherichia coli (strain K12)
UPenicillin-binding protein 3
inhibitor
Bacillus subtilis (strain 168)
UPenicillin-binding protein 4Not AvailableStaphylococcus aureus
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally. The bioavailability of the IM injection is 89%. 8

Volume of distribution

The reported volume of distribution for imipenem ranges from 0.23-0.31 L/kg.Label,3,8

Protein binding

Imipenem is 20% bound to plasma proteins. Label,12

Metabolism

Imipenem is metabolized by renal dehydropeptidase.Label,12

Route of elimination

Approximately 70% of imipenem is excreted in the urine as the parent drug.Label,12

Half life

When given via IV injection imipenem has a half-life of 1 h.Label,3,8 The apparent half-life of the IM injection ranges from 1.3-5.1 h, likely due to slower absorption form the injection site.

Clearance

The total clearance of imipenem is 0.2 L/h/kg.8 When used alone, the renal clearance is 0.05 L/h/kg. In combination with cilastatin the renal clearance of imipenem is 0.15 L/h/kg, likely due to the increased concentration of the parent drug.

Toxicity

In case of overdose with the combination product, including relebactam and cilastatin, it is recommended to provide supportive care.13 Imipenem, cilastatin, and relebactam may be removed via hemodialysis.

Affected organisms
  • Pseudomonas aeruginosa
  • Streptococcus agalactiae
  • Haemophilus influenzae
  • Escherichia coli
  • Staphylococcus aureus
  • Enterococcus faecalis
  • Staphylococcus epidermidis
  • Serratia marcescens
  • Proteus vulgaris
  • Providencia rettgeri
  • Morganella morganii
  • Enterobacter cloacae
  • Klebsiella pneumoniae
  • Haemophilus parainfluenzae
  • Citrobacter freundii
  • Bacteroides thetaiotaomicron
  • Klebsiella aerogenes
  • Bacteroides caccae
  • Bacteroides ovatus
  • Bacteroides stercoris
  • Bacteroides uniformis
  • Bacteroides vulgatus
  • Fusobacterium nucleatum
  • Parabacteroides distasonis
  • Acinetobacter spp.
  • Enterobacter spp.
  • Klebsiella spp.
  • Citrobacter spp.
  • Proteus spp.
  • Bifidobacterium spp.
  • Clostridium spp.
  • Eubacterium spp.
  • Peptococcus spp.
  • Peptostreptococcus spp.
  • Propionibacterium spp.
  • Bacteroides spp.
  • Fusobacterium spp.
  • Serratia spp.
  • Gardnerella vaginalis
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
(R)-warfarinThe risk or severity of bleeding can be increased when Imipenem is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Imipenem is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Imipenem is combined with 4-hydroxycoumarin.
7-NitroindazoleThe therapeutic efficacy of 7-Nitroindazole can be decreased when used in combination with Imipenem.
AcenocoumarolThe risk or severity of bleeding can be increased when Imipenem is combined with Acenocoumarol.
AcepromazineImipenem may increase the neurotoxic activities of Acepromazine.
AceprometazineImipenem may increase the neurotoxic activities of Aceprometazine.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Imipenem.
AcetophenazineAcetophenazine may increase the neurotoxic activities of Imipenem.
AlimemazineAlimemazine may increase the neurotoxic activities of Imipenem.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

References

Synthesis Reference

Maurizio Zenoni, "Imipenem production process." U.S. Patent US20020095034, issued July 18, 2002.

US20020095034
General References
  1. Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. doi: 10.1111/j.1469-0691.2008.02101.x. [PubMed:19076841]
  2. Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. [PubMed:3530614]
  3. Buckley MM, Brogden RN, Barradell LB, Goa KL: Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1992 Sep;44(3):408-44. [PubMed:1382937]
  4. Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. [PubMed:9573653]
  5. Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. [PubMed:3859213]
  6. Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. [PubMed:1921491]
  7. Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. [PubMed:6365872]
  8. Balfour JA, Bryson HM, Brogden RN: Imipenem/cilastatin: an update of its antibacterial activity, pharmacokinetics and therapeutic efficacy in the treatment of serious infections. Drugs. 1996 Jan;51(1):99-136. doi: 10.2165/00003495-199651010-00008. [PubMed:8741235]
  9. Nicolau DP: Carbapenems: a potent class of antibiotics. Expert Opin Pharmacother. 2008 Jan;9(1):23-37. [PubMed:18076336]
  10. Zhanel GG, Wiebe R, Dilay L, Thomson K, Rubinstein E, Hoban DJ, Noreddin AM, Karlowsky JA: Comparative review of the carbapenems. Drugs. 2007;67(7):1027-52. [PubMed:17488146]
  11. Brunton LL, Hilal-Dandan R, Knollmann BC. eds (2018). Goodman & Gilman's: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [ISBN:978-1-25-958473-2]
  12. FDA: Primaxin Label [Link]
  13. FDA: Recarbrio Label [Link]
  14. Drugs@FDA: Primaxin [Link]
External Links
Human Metabolome Database
HMDB0015536
KEGG Compound
C06665
PubChem Compound
104838
PubChem Substance
46505744
ChemSpider
94631
BindingDB
50049708
ChEBI
471744
ChEMBL
CHEMBL148
Therapeutic Targets Database
DAP000459
PharmGKB
PA449968
Wikipedia
Imipenem
ATC Codes
J01DH51 — Imipenem and cilastatin
FDA label
Download (616 KB)
MSDS
Download (45 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedTreatmentInfectious Diseases1
1Not Yet RecruitingOtherSepsis1
1RecruitingTreatmentAcinetobacter Baumannii Infection1
2CompletedTreatmentAbdominal Abscess / Bacterial Infections / Pneumonia / Pneumonia, Bacterial / Ventilator-Associated Pneumonia (VAP)1
2CompletedTreatmentAcute Pyelonephritis / Complicated Urinary Tract Infection1
2CompletedTreatmentComplicated Urinary Tract Infection1
2CompletedTreatmentIntra-Abdominal Infections1
2CompletedTreatmentPyelonephritis / Urinary Tract Infection1
2CompletedTreatmentUrinary Tract Infection1
2TerminatedTreatmentPneumonia, Bacterial1
2TerminatedTreatmentUrinary Tract Infection1
3CompletedTreatmentAbscesses / Cellulitis / Skin-structure infections1
3CompletedTreatmentBacterial Infections1
3CompletedTreatmentComplicated Intra-Abdominal Infections / Complicated Urinary Tract Infection1
3CompletedTreatmentPneumonia, Bacterial2
3CompletedTreatmentHospital-acquired bacterial pneumonia1
3RecruitingTreatmentAcinetobacter Baumannii-calcoaceticus Complex / Bacteremia / Colistin Resistant ABC / Hospital-acquired bacterial pneumonia / Ventilator-associated Bacterial Pneumonia1
3RecruitingTreatmentCritical Illness / Resistant Infection / Traumas1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentUrinary Tract Infection1
3TerminatedTreatmentVentilator-Associated Pneumonia (VAP)1
4Active Not RecruitingTreatmentCritically Ill Patients With ECMO1
4CompletedNot AvailableVentilator-Associated Pneumonia (VAP)1
4CompletedPreventionAcute Pancreatitis (AP)1
4CompletedTreatmentHaematological Malignancies / Neutropenia, Febrile1
4CompletedTreatmentInfection NOS1
4CompletedTreatmentInfection NOS / Pneumonia1
4CompletedTreatmentInfective Endocarditis1
4CompletedTreatmentIntra-Abdominal Infections1
4CompletedTreatmentPatients With Febrile Neutropenia1
4CompletedTreatmentVentilator-Associated Pneumonia (VAP)1
4Enrolling by InvitationTreatmentPatients Who Received Imipenem or Meropenem or Piperacillin/Tazobactam or Sulbactam in ICU1
4RecruitingTreatmentCritical Illness / Mechanical Ventilation Complication1
4RecruitingTreatmentSepsis1
4TerminatedTreatmentUrinary Tract Infection1
4Unknown StatusTreatmentDrug Safety1
4Unknown StatusTreatmentLiver Cirrhosis1
4Unknown StatusTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA) / Ventilator-Associated Pneumonia (VAP)1
4Unknown StatusTreatmentVentilator-associated Bacterial Pneumonia1
Not AvailableActive Not RecruitingTreatmentMetagenomic Next Generation Sequencing / Pneumonia1
Not AvailableCompletedTreatmentFebrile / Hematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1
Not AvailableCompletedTreatmentSpontaneous Bacterial Peritonitis (SBP)1
Not AvailableCompletedTreatmentVentilator-associated Bacterial Pneumonia1
Not AvailableRecruitingNot AvailableChildren; Infection / Newborn; Infection1
Not AvailableRecruitingNot AvailableShock, Septic1
Not AvailableRecruitingNot AvailableTuberculosis Infection1
Not AvailableRecruitingTreatmentSepsis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Cardinal Health
  • Merck & Co.
Dosage forms
FormRouteStrength
PowderNot applicable1 kg/1kg
Injection, powder, for solutionIntravenous
Powder, for solutionIntravenous
Injection, powder, for suspensionIntramuscular
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8487093No2009-11-192029-11-19Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility1E+004 mg/LMERCK INDEX (1996)
pKa3.2MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.776 mg/mLALOGPS
logP-0.19ALOGPS
logP-3.9ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)10.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.22 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity75.84 m3·mol-1ChemAxon
Polarizability31.1 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8406
Blood Brain Barrier-0.9711
Caco-2 permeable-0.6608
P-glycoprotein substrateSubstrate0.7111
P-glycoprotein inhibitor INon-inhibitor0.9011
P-glycoprotein inhibitor IINon-inhibitor0.8328
Renal organic cation transporterNon-inhibitor0.5947
CYP450 2C9 substrateNon-substrate0.7648
CYP450 2D6 substrateNon-substrate0.7854
CYP450 3A4 substrateNon-substrate0.5309
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9125
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9583
Ames testNon AMES toxic0.648
CarcinogenicityNon-carcinogens0.9203
BiodegradationNot ready biodegradable0.9309
Rat acute toxicity1.8089 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9852
hERG inhibition (predictor II)Non-inhibitor0.8603
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
Alpha amino acids and derivatives / Pyrroline carboxylic acids / Azepines / Vinylogous thioesters / Tertiary carboxylic acid amides / Thioenol ethers / Secondary alcohols / Azetidines / Sulfenyl compounds / Azacyclic compounds
show 10 more
Substituents
Thienamycin / Alpha-amino acid or derivatives / Pyrroline carboxylic acid / Pyrroline carboxylic acid or derivatives / Azepine / Vinylogous thioester / Pyrroline / Tertiary carboxylic acid amide / Azetidine / Carboxamide group
show 23 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
carbapenems (CHEBI:471744) / carbapenems (C06665)

Targets

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. Nicolau DP: Carbapenems: a potent class of antibiotics. Expert Opin Pharmacother. 2008 Jan;9(1):23-37. [PubMed:18076336]
  2. Zhanel GG, Wiebe R, Dilay L, Thomson K, Rubinstein E, Hoban DJ, Noreddin AM, Karlowsky JA: Comparative review of the carbapenems. Drugs. 2007;67(7):1027-52. [PubMed:17488146]
  3. Neu HC: Carbapenems: special properties contributing to their activity. Am J Med. 1985 Jun 7;78(6A):33-40. [PubMed:3873871]
  4. Luchi M, Morrison DC, Opal S, Yoneda K, Slotman G, Chambers H, Wiesenfeld H, Lemke J, Ryan JL, Horn D: A comparative trial of imipenem versus ceftazidime in the release of endotoxin and cytokine generation in patients with gram-negative urosepsis. Urosepsis Study Group. J Endotoxin Res. 2000;6(1):25-31. [PubMed:11061029]
  5. FDA: Recarbrio Label [Link]
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. Nicolau DP: Carbapenems: a potent class of antibiotics. Expert Opin Pharmacother. 2008 Jan;9(1):23-37. [PubMed:18076336]
  2. Zhanel GG, Wiebe R, Dilay L, Thomson K, Rubinstein E, Hoban DJ, Noreddin AM, Karlowsky JA: Comparative review of the carbapenems. Drugs. 2007;67(7):1027-52. [PubMed:17488146]
  3. FDA: Recarbrio Label [Link]
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. Nicolau DP: Carbapenems: a potent class of antibiotics. Expert Opin Pharmacother. 2008 Jan;9(1):23-37. [PubMed:18076336]
  2. Zhanel GG, Wiebe R, Dilay L, Thomson K, Rubinstein E, Hoban DJ, Noreddin AM, Karlowsky JA: Comparative review of the carbapenems. Drugs. 2007;67(7):1027-52. [PubMed:17488146]
  3. FDA: Recarbrio Label [Link]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
pbpC
Uniprot ID
P42971
Uniprot Name
Penicillin-binding protein 3
Molecular Weight
74405.915 Da
References
  1. Nicolau DP: Carbapenems: a potent class of antibiotics. Expert Opin Pharmacother. 2008 Jan;9(1):23-37. [PubMed:18076336]
  2. Zhanel GG, Wiebe R, Dilay L, Thomson K, Rubinstein E, Hoban DJ, Noreddin AM, Karlowsky JA: Comparative review of the carbapenems. Drugs. 2007;67(7):1027-52. [PubMed:17488146]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not Available
Gene Name
pbp4
Uniprot ID
P72355
Uniprot Name
Penicillin-binding protein 4
Molecular Weight
48237.14 Da
References
  1. FDA: Primaxin Label [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. FDA: Recarbrio Label [Link]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
No
Actions
Substrate
General Function
Beta-lactamase activity
Specific Function
Not Available
Gene Name
bla
Uniprot ID
P0AD63
Uniprot Name
Beta-lactamase SHV-1
Molecular Weight
31223.635 Da
References
  1. FDA: Recarbrio Label [Link]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
No
Actions
Substrate
General Function
TEM-type are the most prevalent beta-lactamases in enterobacteria; they hydrolyze the beta-lactam bond in susceptible beta-lactam antibiotics, thus conferring resistance to penicillins and cephalosporins. TEM-3 and TEM-4 are capable of hydrolyzing cefotaxime and ceftazidime. TEM-5 is capable of hydrolyzing ceftazidime. TEM-6 is capable of hydrolyzing ceftazidime and aztreonam. TEM-8/CAZ-2, TEM-16/CAZ-7 and TEM-24/CAZ-6 are markedly active against ceftazidime. IRT-4 shows resistance to beta-lactamase inhibitors.
Specific Function
Beta-lactamase activity
Gene Name
bla
Uniprot ID
P62593
Uniprot Name
Beta-lactamase TEM
Molecular Weight
31514.865 Da
References
  1. FDA: Recarbrio Label [Link]
Kind
Protein group
Organism
Escherichia coli
Pharmacological action
No
Actions
Substrate
General Function
Not Available
Specific Function
Beta-lactamase activity

Components:
References
  1. FDA: Recarbrio Label [Link]
Kind
Protein
Organism
Klebsiella pneumoniae
Pharmacological action
Yes
Actions
Substrate
General Function
Not Available
Specific Function
Beta-lactamase activity
Gene Name
KPC-2
Uniprot ID
Q93LQ9
Uniprot Name
Beta-lactamase
Molecular Weight
31114.99 Da
References
  1. Bradford PA, Bratu S, Urban C, Visalli M, Mariano N, Landman D, Rahal JJ, Brooks S, Cebular S, Quale J: Emergence of carbapenem-resistant Klebsiella species possessing the class A carbapenem-hydrolyzing KPC-2 and inhibitor-resistant TEM-30 beta-lactamases in New York City. Clin Infect Dis. 2004 Jul 1;39(1):55-60. doi: 10.1086/421495. Epub 2004 Jun 14. [PubMed:15206053]
  2. FDA: Recarbrio Label [Link]

Drug created on August 29, 2007 12:42 / Updated on November 02, 2019 04:39