Identification

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Name
Meropenem
Accession Number
DB00760  (APRD01097, EXPT02153)
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Meropenem trihydrateFV9J3JU8B1119478-56-7CTUAQTBUVLKNDJ-OBZXMJSBSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Meropenem for InjectionPowder, for solutionIntravenousFresenius Kabi2014-06-05Not applicableCanada
Meropenem for InjectionPowder, for solutionIntravenousSterimax IncNot applicableNot applicableCanada
Meropenem for InjectionPowder, for solutionIntravenousAuro Pharma Inc2017-10-20Not applicableCanada
Meropenem for InjectionPowder, for solutionIntravenousSandoz Canada Incorporated2012-01-26Not applicableCanada
Meropenem for InjectionPowder, for solutionIntravenousAuro Pharma Inc2017-10-20Not applicableCanada
Meropenem for InjectionPowder, for solutionIntravenousSandoz Canada Incorporated2012-01-26Not applicableCanada
Meropenem for InjectionPowder, for solutionIntravenousFresenius Kabi2014-10-20Not applicableCanada
Meropenem for InjectionPowder, for solutionIntravenousSterimax IncNot applicableNot applicableCanada
Meropenem for Injection SdzPowder, for solutionIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Meropenem for Injection SdzPowder, for solutionIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MeropenemInjection, powder, for solution500 mg/10mLIntravenousHospira, Inc.2010-06-24Not applicableUs
MeropenemInjection, powder, for solution500 mg/1IntravenousWG Critical Care, LLC2020-01-09Not applicableUs
MeropenemInjection, powder, for solution1 g/30mLIntravenousDaewoong America Inc.2015-12-182016-10-08Us
MeropenemInjection, powder, for solution1 g/1IntravenousAuroMedics Pharma LLC2017-03-27Not applicableUs
MeropenemInjection, powder, for solution500 mg/10mLIntravenousHospira, Inc.2019-10-09Not applicableUs
MeropenemInjection, powder, for solution500 mg/10mLIntravenousCardinal Health2010-06-232018-06-07Us
MeropenemInjection, powder, for solution500 mg/1IntravenousSagent Pharmaceuticals2017-01-152020-06-30Us
MeropenemInjection1 g/30mLIntravenousGland Pharma Limited2017-04-28Not applicableUs
MeropenemInjection, powder, for solution1 g/20mLIntravenousFresenius Kabi USA, LLC2011-10-26Not applicableUs
MeropenemInjection, powder, for solution500 mg/20mLIntravenousDaewoong America Inc.2015-12-182016-10-08Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Meropenem and Sodium ChlorideMeropenem trihydrate (1 g/50mL) + Sodium chloride (0.9 g/50mL)Injection, solutionIntravenousB. Braun Medical Inc.2015-04-30Not applicableUs
Meropenem and Sodium ChlorideMeropenem trihydrate (500 mg/50mL) + Sodium chloride (0.9 g/50mL)Injection, solutionIntravenousB. Braun Medical Inc.2015-04-30Not applicableUs
VabomereMeropenem trihydrate (1 g/2g) + Vaborbactam (1 g/2g)Injection, powder, for solutionIntravenousThe Medicines Company2017-10-02Not applicableUs
VabomereMeropenem trihydrate (1 g/2g) + Vaborbactam (1 g/2g)Injection, powder, for solutionIntravenousMelinta Therapeutics, Inc.2017-10-02Not applicableUs
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)
Categories
UNII
YOP6PX0BAO
CAS number
96036-03-2
Weight
Average: 383.463
Monoisotopic: 383.151491615
Chemical Formula
C17H25N3O5S
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]

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.

Associated Conditions
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)
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
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
Toxicity

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

Affected organisms
  • Enteric bacteria and other eubacteria
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 Meropenem is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Meropenem is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Meropenem is combined with 4-hydroxycoumarin.
AbacavirMeropenem may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Meropenem 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.
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

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
External Links
Human Metabolome Database
HMDB0014898
KEGG Drug
D02222
PubChem Compound
441130
PubChem Substance
46504928
ChemSpider
389924
BindingDB
50129062
ChEBI
43968
ChEMBL
CHEMBL127
Therapeutic Targets Database
DAP000441
PharmGKB
PA164764445
HET
MEM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Meropenem
ATC Codes
J01DH02 — MeropenemJ01DH52 — Meropenem and vaborbactam
AHFS Codes
  • 08:12.07.08 — Carbapenems
PDB Entries
4euz
FDA label
Download (276 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceBMI >30 kg/m2 / Diabetes / Inflammatory Reaction / Osteoporosis1
0RecruitingTreatmentAntibiotic Resistant Infection1
0RecruitingTreatmentOsteomyelitis1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentGram-Negative Bacterial Infections1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentUrinary Tract Infection1
1RecruitingTreatmentBacterial Infections1
1, 2CompletedTreatmentAcute Pancreatitis (AP)1
1, 2CompletedTreatmentIntra-Abdominal Infections / Necrotizing Enterocolitis1
1, 2CompletedTreatmentMeningitis1
2CompletedTreatmentComplicated Intra-Abdominal Infections1
2CompletedTreatmentComplicated Intra-Abdominal Infections / Complicated Intra-Abdominal Infections (cIAIs)1
2CompletedTreatmentCritical Illness / Hospital Acquired Infections / Pneumonia / Pyrexia / Systemic Inflammatory Response Syndrome (SIRS)1
2CompletedTreatmentPulmonary Tuberculosis (TB)1
2RecruitingTreatmentComplicated Intra-Abdominal Infections1
2RecruitingTreatmentComplicated Urinary Tract Infection / Pyelonephritis1
2RecruitingTreatmentOther Infectious Diseases1
2RecruitingTreatmentPulmonary Tuberculosis (TB)1
2TerminatedTreatmentInfections, Intestinal1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
2TerminatedTreatmentOsteomyelitis1
2TerminatedTreatmentPneumonia, Bacterial1
2, 3CompletedTreatmentVentilator-associated Bacterial Pneumonia1
2, 3RecruitingTreatmentAppendicitis Acute1
2, 3RecruitingTreatmentSepsis1
2, 3TerminatedTreatmentAscites / Liver Cirrhosis / Nosocomial Spontaneous Bacterial Peritonitis1
3CompletedTreatmentAbdominal Infection / Acute Pyelonephritis / Bacteremia / Complicated Urinary Tract Infection / Hospital Acquired Bacterial Pneumonia / Intra Abdominal Infections Complicated / Ventilator-associated Bacterial Pneumonia1
3CompletedTreatmentAbscesses / Cellulitis / Skin-structure infections1
3CompletedTreatmentAcute Pyelonephritis (AP) Due to CRE / Bloodstream Infections (BSI) Due to CRE / Complicated Urinary Tract Infection (cUTI) Due to CRE / Hospital-Acquired Bacterial Pneumonia (HABP) Due to CRE / Ventilator-Associated Bacterial Pneumonia (VABP) Due to CRE1
3CompletedTreatmentAcute Pyelonephritis / Complicated Urinary Tract Infection3
3CompletedTreatmentChronic Lung Diseases / Healthcare-Associated Pneumonia / Hospital-acquired bacterial pneumonia / Ventilator-Associated Pneumonia (VAP)1
3CompletedTreatmentComplicated Appendicitis / Complicated Intra-Abdominal Infections1
3CompletedTreatmentComplicated Intra-Abdominal Infections4
3CompletedTreatmentHealthcare-associated Pneumonia (HCAP) / Hospital-acquired bacterial pneumonia / Ventilator-associated Bacterial Pneumonia1
3CompletedTreatmentLate Onset Neonatal Sepsis1
3CompletedTreatmentPneumonia1
3CompletedTreatmentSepsis1
3CompletedTreatmentSevere Sepsis / Shock, Septic1
3CompletedTreatmentHospital-acquired bacterial pneumonia / Ventilator-Associated Pneumonia (VAP)1
3CompletedTreatmentVentilator-associated Bacterial Pneumonia1
3Not Yet RecruitingTreatmentAcute Pyelonephritis / Complicated Urinary Tract Infection1
3RecruitingTreatmentAcute Pyelonephritis / Urinary Tract Infection1
3RecruitingTreatmentBlood Stream Infections / Pneumonia1
3RecruitingTreatmentComplicated Intra-Abdominal Infections1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentInfection Due to ESBL Escherichia Coli / Infection Due to Multidrug-resistant Escherichia Coli1
3RecruitingTreatmentShock, Septic1
3RecruitingTreatmentUrinary Tract Infection1
3TerminatedTreatmentAbdominal Abscess / Abdominal Pain / Abscess, Intra-Abdominal / Acute Abdomen / Appendicitis / Ileus / Infection / Intestinal Perforations / Peritonitis / Rupture1
3TerminatedTreatmentBacterial Infections1
3TerminatedTreatmentUrinary Tract Infection1
3WithdrawnTreatmentHospital-acquired bacterial pneumonia / Pneumonia, Hospital-Acquired / Ventilator-associated Bacterial Pneumonia / Ventilator-Associated Pneumonia (VAP)1
4Active Not RecruitingTreatmentBronchiectasis1
4Active Not RecruitingTreatmentCystic Fibrosis (CF)1
4CompletedNot AvailableInitial Phase of Severe Sepsis and Septic Shock1
4CompletedNot AvailableVentilator-Associated Pneumonia (VAP)1
4CompletedPreventionPancreatitis,Acute Necrotizing1
4CompletedTreatmentBacterial Infections1
4CompletedTreatmentCentral Nervous System Infections1
4CompletedTreatmentCystic Fibrosis (CF) / Pneumonia / Pseudomonas Aeruginosa Infection1
4CompletedTreatmentGram-Negative Bacterial Infections1
4CompletedTreatmentHaematological Malignancies / Neutropenia, Febrile1
4CompletedTreatmentLower Respiratory Tract Infection (LRTI)1
4CompletedTreatmentPancreatitis1
4CompletedTreatmentSepsis1
4Enrolling by InvitationTreatmentPatients Who Received Imipenem or Meropenem or Piperacillin/Tazobactam or Sulbactam in ICU1
4Not Yet RecruitingTreatmentAntibiotic Resistance, Bacterial / Carbapenem / Clinical Trial / Enterobacteriaceae Infections / Infection Due to ESBL Bacteria / Infection Due to Escherichia Coli / Klebsiella Pneumoniae Infection / Urinary Tract Infection1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4RecruitingTreatmentAntibiotic Resistant Infection / Critical Illness1
4RecruitingTreatmentBacteremia / Beta Lactam Resistant Bacterial Infection / Enterobacteriaceae Infections1
4RecruitingTreatmentBloodstream Infections1
4RecruitingTreatmentSalmonella Typhi Infection1
4RecruitingTreatmentSepsis1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentBloodstream Infections1
4Unknown StatusTreatmentCystic Fibrosis (CF)1
4Unknown StatusTreatmentDrug Safety1
4Unknown StatusTreatmentPancreatitis,Acute Necrotizing1
Not AvailableActive Not RecruitingTreatmentMetagenomic Next Generation Sequencing / Pneumonia1
Not AvailableCompletedNot AvailableAllogenic Blood Stem Cell Transplantation / Neutropenia, Febrile1
Not AvailableCompletedNot AvailableCritical Illness1
Not AvailableCompletedBasic ScienceAlcoholic Hepatitis (AH)1
Not AvailableCompletedTreatmentAppendicitis / Children1
Not AvailableCompletedTreatmentCarbapenem / Clinical Outcome / Critical Illness / Morality / Organ Failure, Multiple / Pharmacodynamics / Pharmacokinetics / Sepsis / Shock, Septic1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1
Not AvailableCompletedTreatmentSepsis1
Not AvailableNot Yet RecruitingNot AvailableCerebral Hemorrhage / Subarachnoid Hemorrhage / Therapeutic Drug Monitoring1
Not AvailableNot Yet RecruitingOtherAnti-Bacterial Agents / Bacterial Infections / Drug Monitoring / Infection / Pharmacokinetics / Respiratory Tract Infections (RTI)1
Not AvailableRecruitingNot AvailableAntibiotic Selection Pressure1
Not AvailableRecruitingNot AvailableChildren; Infection / Newborn; Infection1
Not AvailableRecruitingNot AvailableChildren;Infection1
Not AvailableRecruitingNot AvailableCritical Illness / Infection1
Not AvailableRecruitingNot AvailableEarly Onset Neonatal Sepsis1
Not AvailableRecruitingNot AvailableGeneral Surgery1
Not AvailableRecruitingNot AvailableInfection / Renal Failure1
Not AvailableRecruitingNot AvailableLiver Cirrhosis / Peritonitis bacterial1
Not AvailableRecruitingTreatmentSepsis1
Not AvailableSuspendedBasic ScienceCystic Fibrosis (CF)1
Not AvailableTerminatedNot AvailableCystic Fibrosis Pulmonary Exacerbation1
Not AvailableTerminatedTreatmentAcute on Chronic Liver Failure1
Not AvailableUnknown StatusTreatmentBurkholderia pseudomallei infection1
Not AvailableWithdrawnNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1

Pharmacoeconomics

Manufacturers
  • Hospira inc
  • Astrazeneca uk ltd
Packagers
  • AstraZeneca Inc.
  • Hospira Inc.
  • Zambon Ltd.
  • Zeneca Pharma Inc.
Dosage forms
FormRouteStrength
InjectionIntravenous1 g/30mL
InjectionIntravenous500 mg/20mL
Injection, powder, for solutionIntravenous1 g/20mL
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous1 g/30mL
Injection, powder, for solutionIntravenous500 mg/1
Injection, powder, for solutionIntravenous500 mg/20mL
Injection, powder, for solutionIntravenous500 mg/10mL
Injection, solutionIntravenous
Powder, for solutionIntravenous
Injection, powder, for solutionIntravenous
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)
US4943569No1990-07-242010-06-21Us
CA1322371No1993-09-212010-09-21Canada
US9694025No2017-07-042031-08-08Us
US8680136No2014-03-252031-08-17Us
US10183034No2019-01-222031-08-08Us
US10172874No2019-01-082031-08-08Us
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 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

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
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
Thienamycin / Proline or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Pyrroline carboxylic acid / Pyrroline carboxylic acid or derivatives / Azepine / Vinylogous thioester
show 28 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
pyrrolidinecarboxamide, alpha,beta-unsaturated monocarboxylic acid, carbapenemcarboxylic acid (CHEBI:43968)

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
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. [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. 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. [PubMed:9099227]
  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. [PubMed:11353613]

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. [PubMed:7803882]
  2. Bonfiglio G, Russo G, Nicoletti G: Recent developments in carbapenems. Expert Opin Investig Drugs. 2002 Apr;11(4):529-44. [PubMed:11922861]

Drug created on June 13, 2005 07:24 / Updated on January 18, 2020 13:28