Identification
- Generic Name
- Glutethimide
- DrugBank Accession Number
- DB01437
- Background
Glutethimide is a hypnotic and sedative. Its use has been largely superseded by other drugs.
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Glutethimide (DB01437)
- Weight
- Average: 217.2637
Monoisotopic: 217.110278729 - Chemical Formula
- C13H15NO2
- Synonyms
- 2-Ethyl-2-phenylglutarimide
- Glutethimide
- Glutetimida
Pharmacology
- Indication
For the treatment of insomnia.
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Glutethimide, like the barbiturates, is a hypnotic sedative. It was introduced in 1954 as a safer alternative to barbiturates but was soon determined to be just as likely to cause addiction and withdrawal symptoms.
- Mechanism of action
Glutethimide seems to be a GABA agonist which helps induce sedation. It also induces CYP 2D6. When taken with codeine, it enables the body to convert higher amounts of codeine (higher than the average 5 - 10%) to morphine. This combination of effects enhances sedation.
Target Actions Organism AGamma-aminobutyric acid receptor subunit alpha-1 agonistHumans AGABA(A) Receptor positive allosteric modulatorHumans - Absorption
Variable
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic. Glutethimide is almost completely metabolized.
- Route of elimination
glutethimide is inactivated by conjugation and the metabolites are excreted in urine, only 2% of the parent substance is excreted in urine, up to 2% of the dose has been reported to be found in the faeces.
- Half-life
10-12 hours
- Clearance
Not Available
- Adverse Effects
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In adults, death has been reported after 5 g. The usual lethal dose is 10 to 20g, although survival after a dose of 28 g has been reported.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Glutethimide is combined with 1,2-Benzodiazepine. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Glutethimide. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Glutethimide. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Glutethimide. Agomelatine The risk or severity of CNS depression can be increased when Glutethimide is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Glutethimide. Alimemazine The risk or severity of CNS depression can be increased when Alimemazine is combined with Glutethimide. Almotriptan The risk or severity of CNS depression can be increased when Almotriptan is combined with Glutethimide. Alosetron The risk or severity of CNS depression can be increased when Alosetron is combined with Glutethimide. Alprazolam The risk or severity of CNS depression can be increased when Alprazolam is combined with Glutethimide. 
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- Avoid alcohol.
- Take with or without food. The absorption is unaffected by food.
Products
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- Doriden (U.S.V .) / Elrodorm / Glimid (Polfa Pabianice) / Glutethimid (Balkanpharma) / Noxyron
Categories
- ATC Codes
- N05CE01 — Glutethimide
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperidines
- Sub Class
- Phenylpiperidines
- 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 show 1 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-unsubstituted / Delta-lactam / Dicarboximide / Hydrocarbon derivative show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidines (CHEBI:5439)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- C8I4BVN78E
- CAS number
- 77-21-4
- InChI Key
- JMBQKKAJIKAWKF-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 3-ethyl-3-phenylpiperidine-2,6-dione
- SMILES
- CCC1(CCC(=O)NC1=O)C1=CC=CC=C1
References
- Synthesis Reference
Hoffmann, K. and Tagmann, E.; U.S. Patent 2,673,205; March 23, 1954; assigned to Ciba Pharmaceutical Products, Inc.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015505
- KEGG Drug
- D00532
- KEGG Compound
- C07489
- PubChem Compound
- 3487
- PubChem Substance
- 46506283
- ChemSpider
- 3367
- 4903
- ChEBI
- 5439
- ChEMBL
- CHEMBL1102
- Therapeutic Targets Database
- DAP001305
- PharmGKB
- PA164749505
- Wikipedia
- Glutethimide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 78-81 Hoffmann, K. and Tagmann, E.; U.S. Patent 2,673,205; March 23, 1954; assigned to Ciba Pharmaceutical Products, Inc. water solubility 999 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.90 HANSCH,C ET AL. (1995) logS -2.34 ADME Research, USCD pKa 9.2 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.327 mg/mL ALOGPS logP 1.89 ALOGPS logP 2.13 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 11.69 Chemaxon pKa (Strongest Basic) -6.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.17 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 60.65 m3·mol-1 Chemaxon Polarizability 23.15 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9973 Blood Brain Barrier + 0.996 Caco-2 permeable + 0.5931 P-glycoprotein substrate Substrate 0.6677 P-glycoprotein inhibitor I Non-inhibitor 0.5334 P-glycoprotein inhibitor II Non-inhibitor 0.9611 Renal organic cation transporter Non-inhibitor 0.7747 CYP450 2C9 substrate Non-substrate 0.7785 CYP450 2D6 substrate Non-substrate 0.894 CYP450 3A4 substrate Substrate 0.5173 CYP450 1A2 substrate Non-inhibitor 0.8856 CYP450 2C9 inhibitor Non-inhibitor 0.9101 CYP450 2D6 inhibitor Non-inhibitor 0.8664 CYP450 2C19 inhibitor Non-inhibitor 0.8671 CYP450 3A4 inhibitor Non-inhibitor 0.863 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8527 Ames test Non AMES toxic 0.8254 Carcinogenicity Non-carcinogens 0.8911 Biodegradation Not ready biodegradable 0.9927 Rat acute toxicity 2.5276 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9778 hERG inhibition (predictor II) Non-inhibitor 0.7311
Spectra
- Mass Spec (NIST)
- Download (9.43 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - CI-B GC-MS splash10-014i-0090000000-df13dd29711d257fd7b0 GC-MS Spectrum - EI-B GC-MS splash10-014r-4900000000-8d3add816c0b57475d49 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- 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. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- ChEMBL Compound Report Card [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
- Specific Function
- Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
- Gene Name
- CYP11A1
- Uniprot ID
- P05108
- Uniprot Name
- Cholesterol side-chain cleavage enzyme, mitochondrial
- Molecular Weight
- 60101.87 Da
References
- Walther B, Ghersi-Egea JF, Minn A, Siest G: Brain mitochondrial cytochrome P-450scc: spectral and catalytic properties. Arch Biochem Biophys. 1987 May 1;254(2):592-6. doi: 10.1016/0003-9861(87)90142-1. [Article]
Drug created at July 26, 2007 19:33 / Updated at February 21, 2021 18:51