Imipenem

Identification

Summary

Imipenem is a carbapenem antibiotic normally administered with cilastatin to treat a variety of infections.

Brand Names
Primaxin, Recarbrio
Generic Name
Imipenem
DrugBank Accession Number
DB01598
Background

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 ertapenem 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

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 299.346
Monoisotopic: 299.093976737
Chemical Formula
C12H17N3O4S
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

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatBacterial septicemiaCombination Product in combination with: Cilastatin (DB01597)•••••••••••••••••••••
Used in combination to treatComplicated intra-abdominal infections (ciais) caused by gram-negative bacteriaCombination Product in combination with: Cilastatin (DB01597), Relebactam (DB12377)••••••••••••••••••••••••••
Used in combination to treatComplicated urinary tract infectionCombination Product in combination with: Cilastatin (DB01597)••••••••••••
Used in combination to treatComplicated urinary tract infection caused by gram-negative bacteriaCombination Product in combination with: Relebactam (DB12377), Cilastatin (DB01597)••••••••••••••••••••••••••
Used in combination to treatEndocarditis caused by staphylococcus aureusCombination Product in combination with: Cilastatin (DB01597)•••••••••••••••••••••
Contraindications & Blackbox Warnings
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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
UBeta-lactamase
activator
Proteus vulgaris
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.

Adverse Effects
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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.

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
AcenocoumarolThe risk or severity of bleeding can be increased when Imipenem is combined with Acenocoumarol.
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.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Imipenem is combined with Ambroxol.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Imipenem monohydrate71OTZ9ZE0A74431-23-5GSOSVVULSKVSLQ-JJVRHELESA-N
International/Other Brands
Tienamycin
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BACQURE 500 MGImipenem monohydrate (500 MG/1VIAL) + Cilastatin (500 MG/1VIAL)Injection, powder, for solutionบริษัท แรนแบ็กซี่ (ประเทศไทย) จำกัด2016-11-22Not applicableThailand flag
CILAPEM 500 MG/500 MG IV ENJEKSİYONLUK ÇÖZELTİ HAZIRLAMAK İÇİN TOZ, 1 ADETImipenem (500 mg) + Cilastatin (500 mg)Injection, solutionIntravenousTÜM-EKİP İLAÇ A.Ş.2011-05-06Not applicableTurkey flag
CILAPEM 500 MG/500 MG IV ENJEKSİYONLUK ÇÖZELTİ HAZIRLAMAK İÇİN TOZ, 25 ADETImipenem (500 mg) + Cilastatin (500 mg)Injection, solutionIntravenousTÜM-EKİP İLAÇ A.Ş.2020-08-14Not applicableTurkey flag
IMEPEN 500 MGImipenem monohydrate (500 MG/1VIAL) + Cilastatin (500 MG/1VIAL)Powderบริษัท ฐิติรัตน์สานนท์ จำกัด2013-07-032019-10-21Thailand flag
IMICILA ALVOGENImipenem monohydrate (500 MG/1VIAL) + Cilastatin (500 MG/1VIAL)Injection, powder, for solutionบริษัท อัลโวเจน (ประเทศไทย) จำกัด2016-12-272020-08-20Thailand flag

Categories

ATC Codes
J01DH51 — Imipenem and cilastatinJ01DH56 — Imipenem, cilastatin and relebactam
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
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
Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Amidine / Azacycle / Azepine / Azetidine / Carbonyl group / Carboxamide group / Carboximidamide
show 23 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
carbapenems (CHEBI:471744) / carbapenems (C06665)
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

Chemical Identifiers

UNII
Q20IM7HE75
CAS number
64221-86-9
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

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. [Article]
  2. Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. [Article]
  7. Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. [Article]
  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. [Article]
  9. Nicolau DP: Carbapenems: a potent class of antibiotics. Expert Opin Pharmacother. 2008 Jan;9(1):23-37. [Article]
  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. [Article]
  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 Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [Link]
  14. Drugs@FDA: Primaxin [Link]
Human Metabolome Database
HMDB0015536
KEGG Compound
C06665
PubChem Compound
104838
PubChem Substance
46505744
ChemSpider
94631
BindingDB
50049708
RxNav
1545986
ChEBI
471744
ChEMBL
CHEMBL148
ZINC
ZINC000004097225
Therapeutic Targets Database
DAP000459
PharmGKB
PA449968
Wikipedia
Imipenem
FDA label
Download (616 KB)
MSDS
Download (45 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableVentilator Associated Bacterial Pneumonia (VABP)1
4CompletedPreventionAcute Pancreatitis1
4CompletedTreatmentFebrile Neutropenia1
4CompletedTreatmentFebrile Neutropenia / Hematological Malignancy1
4CompletedTreatmentInfection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Cardinal Health
  • Merck & Co.
Dosage Forms
FormRouteStrength
SolutionParenteral
Injection, solutionIntravenous
SolutionIntravenous
Powder
SolutionIntravenous530.060 mg
PowderNot applicable1 kg/1kg
Injection, powder, for solutionIntravenous250 mg
Injection, powder, for solutionIntravenous500 mg
Powder, for solutionIntravenous
Injection, powder, for solutionParenteral
Injection, powder, for suspensionIntramuscular
Injection, powder, for solutionIntravenous
Injection, powder, for solution
Injection, powder, for suspensionIntravenous
InjectionIntravenous
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8487093No2013-07-162029-11-19US flag

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)3.44Chemaxon
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-MSsplash10-000y-9150000000-462b1a2f1803b594d4d8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-0159000000-582ec7b65277df8d6e44
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f8a-0980000000-de84a98fac10e44ecc6d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-0192000000-02c65a1ca3d9d8d304e7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0920000000-507caa16deacf4fb7eac
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006w-9760000000-d622ae69064d55f317c3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gzc-1940000000-d579527819f7bc33bd7e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.3684058
predicted
DarkChem Lite v0.1.0
[M-H]-174.6214058
predicted
DarkChem Lite v0.1.0
[M-H]-174.24174
predicted
DeepCCS 1.0 (2019)
[M+H]+174.1401058
predicted
DarkChem Lite v0.1.0
[M+H]+173.1885058
predicted
DarkChem Lite v0.1.0
[M+H]+176.59976
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.8322058
predicted
DarkChem Lite v0.1.0
[M+Na]+172.9580058
predicted
DarkChem Lite v0.1.0
[M+Na]+184.55681
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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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. [Article]
  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. [Article]
  3. Neu HC: Carbapenems: special properties contributing to their activity. Am J Med. 1985 Jun 7;78(6A):33-40. [Article]
  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. [Article]
  5. FDA Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [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. [Article]
  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. [Article]
  3. FDA Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [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. [Article]
  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. [Article]
  3. FDA Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [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. [Article]
  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. [Article]
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]
Kind
Protein
Organism
Proteus vulgaris
Pharmacological action
Unknown
Actions
Activator
General Function
Beta-lactamase activity
Specific Function
Hydrolyzes broad-spectrum beta-lactam antibiotics. Active against cephalosporins such as cefuroxime and cefotaxime.
Gene Name
blaB
Uniprot ID
P52664
Uniprot Name
Beta-lactamase
Molecular Weight
32991.385 Da
References
  1. Chen HY, Livermore DM: Comparative in-vitro activity of biapenem against enterobacteria with beta-lactamase-mediated antibiotic resistance. J Antimicrob Chemother. 1994 Mar;33(3):453-64. doi: 10.1093/jac/33.3.453. [Article]

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 Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [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 Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [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 Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [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 Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [Link]
Kind
Protein
Organism
Klebsiella pneumoniae
Pharmacological action
No
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. [Article]
  2. FDA Approved Drug Products: Recarbrio (imipenem, cilastatin, and relebactam) for intravenous injection [Link]

Drug created at August 29, 2007 18:42 / Updated at March 17, 2022 22:24