Meropenem

Identification

Summary

Meropenem is a carbapenem antibiotic used to treat a wide variety of infections in the body.

Brand Names
Merrem, Vabomere
Generic Name
Meropenem
DrugBank Accession Number
DB00760
Background

Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death.

In August 2017, a combination antibacterial therapy under the market name vabomere was approved for treatment of adult patients with complicated urinary tract infections (cUTI). Vabomere consists of meropenem and Vaborbactam and is intravenously admininstered. The treatment aims to resolve infection-related symptoms and achieve negative urine culture, where the infections are proven or strongly suspected to be caused by susceptible bacteria.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 383.463
Monoisotopic: 383.151491615
Chemical Formula
C17H25N3O5S
Synonyms
  • (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • Meropenem
  • Meropenem anhydrous
  • Meropenemum
External IDs
  • Antibiotic SM 7338
  • ICI 194660
  • SM 7338

Pharmacology

Indication

For use as single agent therapy for the treatment of the following infections when caused by susceptible isolates of the designated microorganisms: complicated skin and skin structure infections due to Staphylococcus aureus (b-lactamase and non-b-lactamase producing, methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (excluding vancomycin-resistant isolates), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis and Peptostreptococcus species; complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. Also for use in the treatment of bacterial meningitis caused by Streptococcus pneumoniae, Haemophilus influenzae (b-lactamase and non-b-lactamase-producing isolates), and Neisseria meningitidis.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death.

Mechanism of action

The bactericidal activity of meropenem results from the inhibition of cell wall synthesis. Meropenem readily penetrates the cell wall of most Gram-positive and Gram-negative bacteria to reach penicillin-binding- protein (PBP) targets. Its strongest affinities are toward PBPs 2, 3 and 4 of Escherichia coli and Pseudomonas aeruginosa; and PBPs 1, 2 and 4 of Staphylococcus aureus.

TargetActionsOrganism
AD-alanyl-D-alanine carboxypeptidase DacB
inhibitor
Escherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Approximately 2%.

Metabolism

Primarily excreted unchanged. There is one metabolite which is microbiologically inactive.

Route of elimination

Approximately 70% of the intravenously administered dose is recovered as unchanged meropenem in the urine over 12 hours, after which little further urinary excretion is detectable.

Half-life

Approximately 1 hour in adults and children 2 years of age and older with normal renal function. Approximately 1.5 hours in children 3 months to 2 years of age.

Clearance

Not Available

Adverse Effects
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Toxicity

In mice and rats, large intravenous doses of meropenem (2200-4000 mg/kg) have been associated with ataxia, dyspnea, convulsions, and mortalities.

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
AbacavirMeropenem may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Meropenem which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Meropenem which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Meropenem is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Meropenem which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Meropenem which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Meropenem which could result in a higher serum level.
AclidiniumMeropenem may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineMeropenem may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Meropenem which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Meropenem sodiumNot Available211238-34-5UBQRNADYCUXRBD-NACOAMSHSA-N
Meropenem trihydrateFV9J3JU8B1119478-56-7CTUAQTBUVLKNDJ-OBZXMJSBSA-N
International/Other Brands
Aronem (ACI) / Aropen (Aristopharma) / Carbanem (Sanofi-Aventis) / Erope (Lincoln) / Fulspec (Acme) / I-penam (Incepta) / Merenz (Admac) / Merofit (FHC) / Meronem (AstraZeneca) / Meronis (Neiss) / Meropen (Swiss Parenterals) / Merotec (Zuventus) / Merrem I.V. (AstraZeneca) / Monan (AstraZeneca) / Ropenem (Drug International) / Zeropenem (Sanofi-Aventis)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Meropenem and Sodium ChlorideInjection, solution1 g/50mLIntravenousB. Braun Medical Inc.2015-04-30Not applicableUS flag
Meropenem and Sodium ChlorideInjection, solution500 mg/50mLIntravenousB. Braun Medical Inc.2015-04-30Not applicableUS flag
Meropenem for InjectionPowder, for solution500 mg / vialIntravenousSterimax Inc2021-05-25Not applicableCanada flag
Meropenem for InjectionPowder, for solution1 g / vialIntravenousSandoz Canada Incorporated2012-01-26Not applicableCanada flag
Meropenem for InjectionPowder, for solution1 g / vialIntravenousAuro Pharma Inc2017-10-20Not applicableCanada flag
Meropenem for InjectionPowder, for solution1 g / vialIntravenousSterimax Inc2021-02-22Not applicableCanada flag
Meropenem for InjectionPowder, for solution500 mg / vialIntravenousAuro Pharma Inc2017-10-20Not applicableCanada flag
Meropenem for InjectionPowder, for solution500 mg / vialIntravenousSandoz Canada Incorporated2012-01-26Not applicableCanada flag
Meropenem for Injection SdzPowder, for solution1 g / vialIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Meropenem for Injection SdzPowder, for solution500 mg / vialIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MeropenemInjection, powder, for solution500 mg/1IntravenousAuroMedics Pharma LLC2017-03-27Not applicableUS flag
MeropenemInjection500 mg/20mLIntravenousBluePoint Laboratories2020-08-31Not applicableUS flag
MeropenemInjection, powder, for solution1 g/20mLIntravenousHospira, Inc.2019-10-09Not applicableUS flag
MeropenemInjection500 mg/20mLIntravenousGland Pharma Limited2017-04-28Not applicableUS flag
MeropenemInjection, powder, for solution500 mg/10mLIntravenousCardinal Health2010-06-232017-06-30US flag
MeropenemInjection, powder, for solution1 g/30mLIntravenousDaewoong America Inc.2015-12-182016-10-08US flag
MeropenemInjection, powder, for solution1 g/1IntravenousWG Critical Care, LLC2020-01-09Not applicableUS flag
MeropenemInjection, powder, for solution500 mg/20mLIntravenousAmneal Pharmaceuticals LLC2016-05-09Not applicableUS flag
MeropenemInjection1 g/30mLIntravenousSavior Lifetec Corporation2016-04-19Not applicableUS flag
MeropenemInjection500 mg/20mLIntravenousSandoz Inc2016-08-29Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
VabomereMeropenem trihydrate (1 g/2g) + Vaborbactam (1 g/2g)Injection, powder, for solutionIntravenousThe Medicines Company2017-10-022019-07-31US flag
VabomereMeropenem trihydrate (1 g/2g) + Vaborbactam (1 g/2g)Injection, powder, for solutionIntravenousMelinta Therapeutics, LLC2017-10-02Not applicableUS flag
VaboremMeropenem trihydrate (1 g) + Vaborbactam (1 g)Injection, powder, for solutionIntravenousMenarini International Operations Luxembourg S.A.2020-12-16Not applicableEU flag

Categories

ATC Codes
J01DH02 — MeropenemJ01DH52 — Meropenem and vaborbactam
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
Proline and derivatives / Alpha amino acid amides / Pyrroline carboxylic acids / Pyrrolidinecarboxamides / Azepines / Vinylogous thioesters / Tertiary carboxylic acid amides / Thioenol ethers / Secondary alcohols / Amino acids
show 10 more
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Azacycle / Azepine / Azetidine
show 28 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
pyrrolidinecarboxamide, alpha,beta-unsaturated monocarboxylic acid, carbapenemcarboxylic acid (CHEBI:43968)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
YOP6PX0BAO
CAS number
96036-03-2
InChI Key
DMJNNHOOLUXYBV-PQTSNVLCSA-N
InChI
InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
IUPAC Name
(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)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@]1([C@@H](C)O)C(=O)N2C(C(O)=O)=C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)[C@H](C)[C@]12[H]

References

Synthesis Reference

Yoon Seok Song, Sung Woo Park, Yeon Jung Yoon, Hee Kyoon Yoon, Seong Cheol Moon, Byung Goo Lee, Soo Jin Choi, Sun Ah Jun, "METHOD FOR PREPARING MEROPENEM USING ZINC POWDER." U.S. Patent US20120065392, issued March 15, 2012.

US20120065392
General References
Not Available
Human Metabolome Database
HMDB0014898
KEGG Drug
D02222
PubChem Compound
441130
PubChem Substance
46504928
ChemSpider
389924
BindingDB
50129062
RxNav
1546029
ChEBI
43968
ChEMBL
CHEMBL127
ZINC
ZINC000003808779
Therapeutic Targets Database
DAP000441
PharmGKB
PA164764445
PDBe Ligand
MEM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Meropenem
AHFS Codes
  • 08:12.07.08 — Carbapenems
PDB Entries
4euz
FDA label
Download (276 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentBloodstream Infections1
4CompletedNot AvailableInitial Phase of Severe Sepsis and Septic Shock1
4CompletedNot AvailableVentilator-associated Bacterial Pneumonia / Ventilator-Associated Pneumonia (VAP)1
4CompletedPreventionPancreatitis,Acute Necrotizing1
4CompletedTreatmentBacterial Infections1
4CompletedTreatmentBronchiectasis1
4CompletedTreatmentCentral Nervous System Infections1
4CompletedTreatmentCystic Fibrosis (CF) / Pneumonia / Pseudomonas Aeruginosa Infection1
4CompletedTreatmentFebrile Neutropenia / Haematological Malignancies1
4CompletedTreatmentGram-Negative Bacterial Infections1

Pharmacoeconomics

Manufacturers
  • Hospira inc
  • Astrazeneca uk ltd
Packagers
  • AstraZeneca Inc.
  • Hospira Inc.
  • Zambon Ltd.
  • Zeneca Pharma Inc.
Dosage Forms
FormRouteStrength
Injection, powder, for solutionParenteral
Injection, powder, lyophilized, for solutionIntravenous1000 mg
Injection, powder, for solutionIntravenous500 mg
InjectionIntravenous1 g/30mL
InjectionIntravenous500 mg/20mL
Injection, powder, for solutionIntravenous
Injection, powder, for solutionIntravenous1 g/20mL
Injection, powder, for solutionIntravenous1 g/30mL
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous500 mg/10mL
Injection, powder, for solutionIntravenous500 mg/20mL
Injection, powder, for solutionIntravenous500 mg/1
Injection, powder, for solutionIntravenous0.5 g
Injection, powder, for solutionIntramuscular; Intravenous500 mg
Injection, solutionIntravenous1 g/50mL
Injection, solutionIntravenous500 mg/50mL
Injection, solutionIntravenous
Powder, for solutionIntravenous1 g / vial
Powder, for solutionIntravenous500 mg / vial
Injection, powder, for solutionIntravenous1000 mg
Injection, powder, for solutionIntravenous1 g
InjectionIntravenous
Injection, powder, for solutionIntravenous; Parenteral
Powder, for solutionIntravenous
Powder
Injection, powder, for solution
Injection, powder, lyophilized, for solutionIntravenous1 g
Injection, powder, for solutionIntravenous
Powder500 mg/1vial
Injection, powder, for solution500 mg/1vial
Prices
Unit descriptionCostUnit
Merrem 1 gm Solution Vial81.32USD vial
Merrem iv 1 gm vial78.19USD vial
Merrem 500 mg Solution Vial48.79USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US4943569No1990-07-242010-06-21US flag
CA1322371No1993-09-212010-09-21Canada flag
US9694025No2017-07-042031-08-08US flag
US8680136No2014-03-252031-08-17US flag
US10183034No2019-01-222031-08-08US flag
US10172874No2019-01-082031-08-08US flag
US10561675No2011-08-082031-08-08US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySparinglyNot Available
logP-0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.63 mg/mLALOGPS
logP-0.69ALOGPS
logP-4.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.18 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.89 m3·mol-1ChemAxon
Polarizability39.29 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7086
Blood Brain Barrier-0.9901
Caco-2 permeable-0.6556
P-glycoprotein substrateSubstrate0.8057
P-glycoprotein inhibitor INon-inhibitor0.6779
P-glycoprotein inhibitor IINon-inhibitor0.952
Renal organic cation transporterNon-inhibitor0.9053
CYP450 2C9 substrateNon-substrate0.8286
CYP450 2D6 substrateNon-substrate0.8136
CYP450 3A4 substrateSubstrate0.6007
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9559
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9798
Ames testNon AMES toxic0.68
CarcinogenicityNon-carcinogens0.8623
BiodegradationNot ready biodegradable0.8801
Rat acute toxicity1.9158 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9969
hERG inhibition (predictor II)Non-inhibitor0.8683
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

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

Targets

Drugtargets
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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
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Kanazawa K, Nouda H, Sunagawa M: Structure-activity relationships of carbapenem compounds to anti-Haemophilus influenzae activity and affinity for penicillin-binding proteins. Effect of 1 beta-methyl group and C-2 side chain. J Antibiot (Tokyo). 1997 Feb;50(2):162-8. [Article]
  4. Ubukata K, Shibasaki Y, Yamamoto K, Chiba N, Hasegawa K, Takeuchi Y, Sunakawa K, Inoue M, Konno M: Association of amino acid substitutions in penicillin-binding protein 3 with beta-lactam resistance in beta-lactamase-negative ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2001 Jun;45(6):1693-9. [Article]

Enzymes

Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Unknown
Actions
Substrate
General Function
Penicillin binding
Specific Function
Hydrolyzes both carbenicillin and oxacillin.
Gene Name
bla
Uniprot ID
P14489
Uniprot Name
Beta-lactamase OXA-10
Molecular Weight
29506.575 Da
References
  1. Pryka RD, Haig GM: Meropenem: a new carbapenem antimicrobial. Ann Pharmacother. 1994 Sep;28(9):1045-54. [Article]
  2. Bonfiglio G, Russo G, Nicoletti G: Recent developments in carbapenems. Expert Opin Investig Drugs. 2002 Apr;11(4):529-44. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2021 01:52