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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014898
Secondary Accession Numbers
  • HMDB14898
Metabolite Identification
Common NameMeropenem
DescriptionMeropenem, also known as merrem I.V. or MEPM, 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. Meropenem is a drug which is used 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. Based on a literature review a significant number of articles have been published on Meropenem.
Structure
Data?1582753233
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 Weight383.463
Monoisotopic Molecular Weight383.151491615
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
CAS Registry Number119478-56-7
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 Identifier
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.63 g/LNot Available
LogP-0.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.6431661259
DarkChem[M-H]-181.31231661259
DeepCCS[M-2H]-221.40130932474
DeepCCS[M+Na]+196.53530932474
AllCCS[M+H]+186.632859911
AllCCS[M+H-H2O]+184.232859911
AllCCS[M+NH4]+188.832859911
AllCCS[M+Na]+189.432859911
AllCCS[M-H]-191.032859911
AllCCS[M+Na-2H]-191.332859911
AllCCS[M+HCOO]-191.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Meropenem[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]4587.7Standard polar33892256
Meropenem[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]2961.2Standard non polar33892256
Meropenem[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]3377.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Meropenem,1TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]122955.5Semi standard non polar33892256
Meropenem,1TMS,isomer #2C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]122934.5Semi standard non polar33892256
Meropenem,1TMS,isomer #3C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]122852.8Semi standard non polar33892256
Meropenem,2TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]122879.5Semi standard non polar33892256
Meropenem,2TMS,isomer #2C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]122824.6Semi standard non polar33892256
Meropenem,2TMS,isomer #3C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]122816.3Semi standard non polar33892256
Meropenem,3TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]122849.4Semi standard non polar33892256
Meropenem,3TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]123256.0Standard non polar33892256
Meropenem,3TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]123776.3Standard polar33892256
Meropenem,1TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]123158.9Semi standard non polar33892256
Meropenem,1TBDMS,isomer #2C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]123164.0Semi standard non polar33892256
Meropenem,1TBDMS,isomer #3C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]123074.9Semi standard non polar33892256
Meropenem,2TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]123316.8Semi standard non polar33892256
Meropenem,2TBDMS,isomer #2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]123236.9Semi standard non polar33892256
Meropenem,2TBDMS,isomer #3C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]123240.9Semi standard non polar33892256
Meropenem,3TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]123456.1Semi standard non polar33892256
Meropenem,3TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]123942.3Standard non polar33892256
Meropenem,3TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]123981.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Meropenem GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g6r-9165000000-bfa50046e33decc913f02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meropenem GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9320210000-71603485baf0ee1f92c62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meropenem GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 10V, Positive-QTOFsplash10-01ox-0936000000-857a771e636fb53260ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 20V, Positive-QTOFsplash10-02tc-1977000000-43d0012adc5dc96ecabd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 40V, Positive-QTOFsplash10-0hfx-9840000000-2ccf21d5dcd32f3989c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 10V, Negative-QTOFsplash10-000i-0229000000-f9d8bdfc2564aeca32ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 20V, Negative-QTOFsplash10-000i-9521000000-83bc2070b161829e83c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 40V, Negative-QTOFsplash10-0002-2900000000-e17d924d7e76927643732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 10V, Positive-QTOFsplash10-001i-0009000000-5e44660aff42cac149bd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 20V, Positive-QTOFsplash10-00lr-0009000000-4dd3b9244a8243c4b20d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 40V, Positive-QTOFsplash10-0udi-4911000000-def7d662e5166c4d5e942021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 10V, Negative-QTOFsplash10-001i-0009000000-d7eed5c18e5f3c6f6f922021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 20V, Negative-QTOFsplash10-017l-1289000000-11238b0e8232b05612fc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meropenem 40V, Negative-QTOFsplash10-08nc-3294000000-363e013578d0e013c8002021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00760 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00760 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00760
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389924
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMeropenem
METLIN IDNot Available
PubChem Compound441130
PDB IDNot Available
ChEBI ID43968
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available