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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:37:59 UTC
HMDB IDHMDB0014448
Secondary Accession Numbers
  • HMDB14448
Metabolite Identification
Common NameErtapenem
DescriptionErtapenem, also known as invanz or ertapenem sodium, 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. Ertapenem is a drug which is used for the treatment the following moderate to severe infections caused by susceptible isolates of the designated microorganisms: (1) complicated intra-abdominal infections due to escherichia coli, clostridium clostridioforme, eubacterium lentum, peptostreptococcus species, bacteroides fragilis, bacteroides distasonis, bacteroides ovatus, bacteroides thetaiotaomicron, or bacteroides uniformis, (2) complicated skin and skin structure infections, including diabetic foot infections without osteomyelitis due to staphylococcus aureus (methicillin susceptible isolates only), streptococcus agalactiae, streptococcus pyogenes, escherichia coli, klebsiella pneumoniae, proteus mirabilis, bacteroides fragilis, peptostreptococcus species, porphyromonas asaccharolytica, or prevotella bivia, (3) community acquired pneumonia due to streptococcus pneumoniae (penicillin susceptible isolates only) including cases with concurrent bacteremia, haemophilus influenzae (beta-lactamase negative isolates only), or moraxella catarrhalis, (4) complicated urinary tract infections including pyelonephritis due to escherichia coli, including cases with concurrent bacteremia, or klebsiella pneumoniae, (5) acute pelvic infections including postpartum endomyometritis, septic abortion and post surgical gynecologic infections due to streptococcus agalactiae, escherichia coli, bacteroides fragilis, porphyromonas asaccharolytica, peptostreptococcus species, or prevotella bivia. Based on a literature review very few articles have been published on Ertapenem.
Structure
Data?1582753181
Synonyms
ValueSource
(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
InvanzKegg
(1R,5S,6S,8R,2's,4's)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylateGenerator
(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-carboxylateGenerator
InvanozHMDB
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
SMILES
[H][C@]12[C@@H](C)C(S[C@]3([H])CN[C@@]([H])(C3)C(=O)NC3=CC=CC(=C3)C(O)=O)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O
InChI Identifier
InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
InChI KeyJUZNIMUFDBIJCM-ANEDZVCMSA-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
  • 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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.29 g/LNot Available
LogP0.3Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP-0.2ALOGPS
logP-3.2ChemAxon
logS-3.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available208.4531661259
DarkChem[M-H]-PredictedNot Available198.12831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Ertapenem,1TMS,#13977.5347https://arxiv.org/abs/1905.12712
Ertapenem,1TMS,#23987.7244https://arxiv.org/abs/1905.12712
Ertapenem,1TMS,#33977.0947https://arxiv.org/abs/1905.12712
Ertapenem,1TMS,#43936.8242https://arxiv.org/abs/1905.12712
Ertapenem,1TMS,#53822.926https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#13867.26https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#23850.0986https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#33825.4976https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#43707.8774https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#53851.9128https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#63852.3489https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#73738.879https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#83830.9043https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#93732.0457https://arxiv.org/abs/1905.12712
Ertapenem,2TMS,#103687.368https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#13773.7769https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#23774.7498https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#33664.0264https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#43774.5398https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#53643.0183https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#63635.6646https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#73790.7073https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#83686.5247https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#93673.4749https://arxiv.org/abs/1905.12712
Ertapenem,3TMS,#103678.0085https://arxiv.org/abs/1905.12712
Ertapenem,1TBDMS,#14215.0425https://arxiv.org/abs/1905.12712
Ertapenem,1TBDMS,#24185.0137https://arxiv.org/abs/1905.12712
Ertapenem,1TBDMS,#34205.4644https://arxiv.org/abs/1905.12712
Ertapenem,1TBDMS,#44128.474https://arxiv.org/abs/1905.12712
Ertapenem,1TBDMS,#54074.0059https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#14284.4287https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#24304.724https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#34227.0093https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#44158.3115https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#54280.1406https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#64222.78https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#74173.902https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#84235.206https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#94187.224https://arxiv.org/abs/1905.12712
Ertapenem,2TBDMS,#104144.294https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#14386.9775https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#24351.876https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#34267.8677https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#44361.823https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#54273.238https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#64275.132https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#74357.4355https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#84283.8423https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#94296.248https://arxiv.org/abs/1905.12712
Ertapenem,3TBDMS,#104304.83https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052s-9534600000-4519573496014739b64d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-1330109000-3e4c64387677650a48682017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0671900000-9c71265b6eb31d52d9252016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-2594700000-77fee4b13a6be5eda7872016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0i03-7940000000-5180d6afb461bc02edcc2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0112900000-eb2b3b9bec00b61e40d82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9522100000-19d44a1137bf99ec22b42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-0910000000-bfbef538a800a2a9369a2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
References
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 ]