Imipenem

Common Name

Imipenem Description

Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many mlitiresistant 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

Synonyms

Value Source (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-Ethylslifanyl)-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 (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-Ethylslifanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylateGenerator (5R,6S)-3-(2-formimidoylamino-Ethylsliphanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylateGenerator (5R,6S)-3-(2-formimidoylamino-Ethylsliphanyl)-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, anhydrousMeSH N FormimidoylthienamycinMeSH Anhydrous imipenemMeSH Anhydrous, imipenemMeSH

Chemical Formlia

C₁₂H₁₇N₃O₄S Average Molecliar Weight

299.346 Monoisotopic Molecliar Weight

299.093976737 IUPAC Name

(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}slifanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Traditional Name

zienam CAS Registry Number

74431-23-5 SMILES

InChI Identifier

InChI Key

ZSKVGTPCRGIANV-ZXFLCMHBSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine slifur atom replaced by carbon, the slifur then becoming the first atom in the side chain. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Lactams Sub Class

Beta lactams Direct Parent

Thienamycins Alternative Parents

Alpha amino acids and derivatives

Pyrroline carboxylic acids

Azepines

Vinylogous thioesters

Tertiary carboxylic acid amides

Thioenol ethers

Secondary alcohols

Azetidines

Slifenyl compounds

Azacyclic compounds

Carboxamidines

Carboximidamides

Carboxylic acids

Monocarboxylic acids and derivatives

Formamidines

Carbonyl compounds

Organopnictogen compounds

Hydrocarbon derivatives

Imines

Organic oxides

Substituents

Thienamycin

Alpha-amino acid or derivatives

Pyrroline carboxylic acid

Pyrroline carboxylic acid or derivatives

Azepine

Vinylogous thioester

Pyrroline

Tertiary carboxylic acid amide

Azetidine

Carboxamide group

Secondary alcohol

Thioenolether

Slifenyl compound

Carboximidamide

Azacycle

Amidine

Formamidine

Carboxylic acid amidine

Carboxylic acid derivative

Carboxylic acid

Monocarboxylic acid or derivatives

Hydrocarbon derivative

Imine

Organonitrogen compound

Organooxygen compound

Organoslifur compound

Carbonyl group

Alcohol

Organic oxygen compound

Organopnictogen compound

Organic oxide

Organic nitrogen compound

Aliphatic heteropolycyclic compound

Molecliar Framework

Aliphatic heteropolycyclic compounds External Descriptors

carbapenems (CHEBI:471744 )

carbapenems (C06665 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Anti-Bacterial Agents

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Extracellliar

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility7.76e-01 g/LNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.78 mg/mLALOGPS 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 Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01598

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01598

21059682

details

Abnormal Concentrations

Not Available Predicted Concentrations

Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01598 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

94631 KEGG Compound ID

C06665 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Imipenem NuGOwiki Link

HMDB15536 Metagene Link

HMDB15536 METLIN ID

Not Available PubChem Compound

104838 PDB ID

Not Available ChEBI ID

471744

Product: Actinomycin D

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. 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 ]
2. 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 ]
3. Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. [PubMed:1921491 ]
4. Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. [PubMed:3530614 ]
5. 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 ]
6. 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 ]
7. 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 ]
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 ]

PMID: 12954047