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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:47 UTC
HMDB IDHMDB0015536
Secondary Accession Numbers
  • HMDB15536
Metabolite Identification
Common NameImipenem
DescriptionSemisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with cilastatin, a renal dipeptidase inhibitor. [PubChem]
Structure
Data?1582753307
Synonyms
ValueSource
(5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acidChEBI
(5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acidChEBI
(5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeureChEBI
Imipenem anhydrousChEBI
ImipenemumChEBI
N-Formimidoyl thienamycinChEBI
N-FormimidoylthienamycinChEBI
IPMKegg
(5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylateGenerator
(5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylateGenerator
(5R,6S)-3-(2-Formimidoylamino-ethylsulphanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylateGenerator
(5R,6S)-3-(2-Formimidoylamino-ethylsulphanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acidGenerator
ImipemideHMDB
Imipenem, N-formimidoyl thienamycinHMDB
IMPHMDB
Imipenem, anhydrousHMDB
N FormimidoylthienamycinHMDB
Anhydrous imipenemHMDB
Anhydrous, imipenemHMDB
Chemical FormulaC12H17N3O4S
Average Molecular Weight299.346
Monoisotopic Molecular Weight299.093976737
IUPAC Name(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Traditional Namezienam
CAS Registry Number74431-23-5
SMILES
[H][C@]12CC(SCC\N=C\N)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O
InChI Identifier
InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
InChI KeyZSKVGTPCRGIANV-ZXFLCMHBSA-N
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.
KingdomInorganic compounds
Super ClassHomogeneous metal compounds
ClassHomogeneous transition metal compounds
Sub ClassNot Available
Direct ParentHomogeneous transition metal compounds
Alternative ParentsNot Available
Substituents
  • Homogeneous transition metal
Molecular FrameworkNot Available
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.78 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP-0.19ALOGPS
logP-3.9ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)10.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity75.84 m³·mol⁻¹ChemAxon
Polarizability31.1 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-9150000000-462b1a2f1803b594d4d8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9416300000-144f90b8d8b4d5b915f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0h3s-3973000000-885401af8e32fab56277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-3490000000-71a354ac25ef670f7e55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r5-8910000000-6be5fb1963bd187b30b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-3390000000-bdd7825d35f4fa7782d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-9630000000-fc0b37e2773e0385e24fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7o-9700000000-2d93b0c62bb2866f1242Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 DB01598 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01598 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01598
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID94631
KEGG Compound IDC06665
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImipenem
METLIN IDNot Available
PubChem Compound104838
PDB IDNot Available
ChEBI ID471744
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Buckley MM, Brogden RN, Barradell LB, Goa KL: Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1992 Sep;44(3):408-44. [PubMed:1382937 ]
  2. Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. [PubMed:1921491 ]
  3. Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. [PubMed:3530614 ]
  4. Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241. [PubMed:3552595 ]
  5. Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. [PubMed:3859213 ]
  6. Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. [PubMed:6365872 ]
  7. Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. [PubMed:9573653 ]
  8. Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. doi: 10.1111/j.1469-0691.2008.02101.x. [PubMed:19076841 ]