Meropenem (CED0001306)

Record Information
Version1.0
Creation Date2016-05-22 05:11:43 UTC
Update Date2026-08-19 21:33:43 UTC
Accession NumberCHEM018371
Identification
Common NameMeropenem
ClassSmall Molecule
Description
Meropenem is an organic compound with the formula C17H25N3O5S and an average molecular weight of 383.46 g/mol. Meropenem belongs to the beta lactams, a subclass of lactams within the organic compounds. It is categorized as an organoheterocyclic compound. This substance is found in or released from two recorded sources: pharmaceuticals & veterinary products, specifically antibiotics and beta-lactam antibacterials, and healthcare. Recorded exposure routes for this compound include oral, intravenous, and inhalation. In terms of biological activity, meropenem acts as an inhibitor of the protein target D-alanyl-D-alanine carboxypeptidase DacB (dacB).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylIC ACIDChEBI
(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 acidChEBI
Antibiotic SM 7338ChEBI
MEPMChEBI
Meropenem anhydrousChEBI
MeropenemumChEBI
Merrem i.v.Kegg
MeronemKegg
(1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylateGenerator
(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-carboxylateGenerator
3-(5-Dimethylcarbamoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acidHMDB
MerremHMDB
RonemHMDB
PenemHMDB
Chemical FormulaC17H25N3O5S
Average Molecular Mass383.463 g/mol
Monoisotopic Mass383.151 g/mol
CAS Registry Number96036-03-2
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
Traditional Namemeropenem
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]
InChI IdentifierInChI=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
InChI KeyDMJNNHOOLUXYBV-PQTSNVLCSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentThienamycins
Alternative Parents
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
  • Pyrrolidine
  • Pyrroline
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Amino acid
  • Thioenolether
  • Secondary alcohol
  • Secondary amine
  • Sulfenyl compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.63 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.89 m³·mol⁻¹ChemAxon
Polarizability39.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0g6r-9165000000-bfa50046e33decc913f0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dl-9320210000-71603485baf0ee1f92c6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-0936000000-857a771e636fb53260aeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02tc-1977000000-43d0012adc5dc96ecabdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0hfx-9840000000-2ccf21d5dcd32f3989c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0229000000-f9d8bdfc2564aeca32aeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9521000000-83bc2070b161829e83c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-2900000000-e17d924d7e7692764373Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-5e44660aff42cac149bdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-0009000000-4dd3b9244a8243c4b20dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-4911000000-def7d662e5166c4d5e94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-d7eed5c18e5f3c6f6f92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-017l-1289000000-11238b0e8232b05612fcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08nc-3294000000-363e013578d0e013c800Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5099.0Log mg/kg[2900:9100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Meropenem Drug Metabolism Action Pathway
Meropenem Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamase OXA-48Q6XEC0Klebsiella pneumoniaePredicted (SEA)0.0778492
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)53.8717
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)6975.83
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)7595.2
Click to view 3D structureBeta-lactamase GES-13D1MIX9Pseudomonas aeruginosaPredicted (SEA)5.29375
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)6473.16
Stromelysin-1 structureClick to view 3D structureStromelysin-1P08254HumansPredicted (SEA)6098.63
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)6974.51
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)2024.7
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)1313.47
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)7440.44
Click to view 3D structureHemagglutininP03438Influenza A virus (strain A/X-31 H3N2)Predicted (SEA)57.9198
Lymphocyte activation gene 3 protein structureClick to view 3D structureLymphocyte activation gene 3 proteinP18627HumansPredicted (SEA)159.202
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)7316.81
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)6853.92
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)7737.9
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)24.3668
Disintegrin and metalloproteinase domain-containing protein 17 structureClick to view 3D structureDisintegrin and metalloproteinase domain-containing protein 17P78536HumansPredicted (SEA)6767.51
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)7383.22
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)7001.6
Chromatin remodeling regulator CECR2 structureClick to view 3D structureChromatin remodeling regulator CECR2Q9BXF3HumansPredicted (SEA)4888.23
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)6350.16
Bromodomain-containing protein 4 structureClick to view 3D structureBromodomain-containing protein 4O60885HumansPredicted (SEA)7250.72
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)6851.82
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)6036.97
Concentrations
Not Available
External Links
DrugBank IDDB00760
HMDB IDHMDB0014898
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMeropenem
Chemspider ID389924
ChEBI ID43968
PubChem Compound ID441130
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10776838
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11069213
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18611786
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18645546
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=28343819
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28371721
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=28583381
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=28669829
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28677407
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7588092