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Glutethimide

July 24, 2017
Common Name

Glutethimide Description

Glutethimide is only found in individuals that have used or taken this drug. It is a hypnotic and sedative. Its use has been largely superseded by other drugs. [PubChem]Glutethimide seems to be a GABA agonist which helps induced sedation. It also induces CYP 2D6. When taken with codeine, it enables the body to convert higher amounts of the codeine (higher than the average 5 – 10%) to morphine. The general sedative effect also adds to the power of the combination. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2-Ethyl-2-phenylglutarimideKegg DoridenKegg GlutathimidHMDB GlutethimidHMDB GlutetimidHMDB GlutetimideHMDB GluthetimideHMDB NoxironMeSH

Chemical Formlia

C13H15NO2 Average Molecliar Weight

217.2637 Monoisotopic Molecliar Weight

217.110278729 IUPAC Name

3-ethyl-3-phenylpiperidine-2,6-dione Traditional Name

glutethimide CAS Registry Number

77-21-4 SMILES

CCC1(CCC(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)

InChI Key

JMBQKKAJIKAWKF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Piperidines Direct Parent

Phenylpiperidines Alternative Parents

  • Piperidinediones
  • Delta lactams
  • Benzene and substituted derivatives
  • N-unsubstituted carboxylic acid imides
  • Dicarboximides
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Phenylpiperidine
  • Piperidinedione
  • Delta-lactam
  • Piperidinone
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • piperidines (CHEBI:5439 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Hypnotics and Sedatives

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point84 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3.27e-01 g/LNot Available LogP1.90HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.33 mg/mLALOGPS logP1.89ALOGPS logP2.13ChemAxon logS-2.8ALOGPS pKa (Strongest Acidic)11.69ChemAxon pKa (Strongest Basic)-6.7ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area46.17 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity60.65 m3·mol-1ChemAxon Polarizability23.15 Å3ChemAxon 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

  • 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 DB01437

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01437

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01437 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

    3367 KEGG Compound ID

    C07489 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Glutethimide NuGOwiki Link

    HMDB15505 Metagene Link

    HMDB15505 METLIN ID

    Not Available PubChem Compound

    3487 PDB ID

    Not Available ChEBI ID

    251300

    Product: Acetaminophen

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

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
    Gene Name:
    CYP11A1
    Uniprot ID:
    P05108
    Molecular weight:
    60101.87
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
    Gene Name:
    CYP2D6
    Uniprot ID:
    P10635
    Molecular weight:
    55768.94
    References
    1. Pearson MW, Roberts CJ: Drug induction of hepatic enzymes in the elderly. Age Ageing. 1984 Sep;13(5):313-6. [PubMed:6496244 ]
    2. Petik D, Acs N, Banhidy F, Czeizel AE: A study of the effects of large doses of glutethimide that were used for self-poisoning during pregnancy on human fetuses. Toxicol Ind Health. 2008 Feb-Mar;24(1-2):69-78. doi: 10.1177/0748233708089014. [PubMed:18818183 ]
    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRA1
    Uniprot ID:
    P14867
    Molecular weight:
    51801.4
    References
    1. Skerritt JH, Johnston GA: Interactions of some anaesthetic, convulsant, and anticonvulsant drugs at GABA-benzodiazepine receptor-ionophore complexes in rat brain synaptosomal membranes. Neurochem Res. 1983 Oct;8(10):1351-62. [PubMed:6318143 ]

    PMID: 26669264

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