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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:41 UTC
Secondary Accession Numbers
  • HMDB14448
Metabolite Identification
Common NameErtapenem
DescriptionErtapenem is only found in individuals that have used or taken this drug. It is a carbapenem antibiotic marketed by Merck as Invanz®. It is structurally very similar to meropenem in that it possess a 1-beta-methyl group. [Wikipedia ]The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3. Ertapenem is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Ertapenem is hydrolyzed by metallo-beta-lactamases.
(1R,5S,6S,8R,2's,4's)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acidChEBI
(4R,5S,6S)-3-((3S,5S)-5-((3-Carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acidChEBI
Ertapenem sodiumHMDB
Chemical FormulaC22H25N3O7S
Average Molecular Weight475.515
Monoisotopic Molecular Weight475.141320859
IUPAC Name(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Traditional Nameertapenem
CAS Registry Number153832-46-3
InChI Identifier
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
Sub ClassBeta lactams
Direct ParentThienamycins
Alternative Parents
  • Thienamycin
  • Acylaminobenzoic acid or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Benzoic acid or derivatives
  • Benzoic acid
  • Anilide
  • Benzoyl
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrroline carboxylic acid
  • Pyrroline carboxylic acid or derivatives
  • N-arylamide
  • Azepine
  • Vinylogous thioester
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrroline
  • Pyrrolidine
  • Amino acid
  • Thioenolether
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Azacycle
  • Secondary amine
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.29 g/LNot Available
LogP0.3Not Available
Predicted Properties
Water Solubility0.29 g/LALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)9.03ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area156.27 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity121.8 m³·mol⁻¹ChemAxon
Polarizability48.77 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052s-9534600000-4519573496014739b64dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-1330109000-3e4c64387677650a4868Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0671900000-9c71265b6eb31d52d925Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-2594700000-77fee4b13a6be5eda787Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0i03-7940000000-5180d6afb461bc02edccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0112900000-eb2b3b9bec00b61e40d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9522100000-19d44a1137bf99ec22b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-0910000000-bfbef538a800a2a9369aSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00303 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00303 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00303
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID132758
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkErtapenem
METLIN IDNot Available
PubChem Compound150610
PDB IDNot Available
ChEBI ID404903
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nix DE, Majumdar AK, DiNubile MJ: Pharmacokinetics and pharmacodynamics of ertapenem: an overview for clinicians. J Antimicrob Chemother. 2004 Jun;53 Suppl 2:ii23-8. [PubMed:15150180 ]