Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1769)
Drug Name
Glutethimide
Synonyms
Glimid; Glutarimide, 2-ethyl-2-phenyl-; Glutathimid; Glutethimid; Glutethimidum; Glutetimid; Glutetimide; Glutetimide [DCIT]; Glutetimidu; Glutetimidu [Polish]; Gluthetimide; Noxiron; Noxyron; Ondasil; Rigenox; Sarodormin; Alfimid; Doriden; Doriden-sed; Dorimide; Elrodorm; dl-Glutethimide; glutethimide; 2-Ethyl-2-phenylglutarimide; 2-Phenyl-2-ethylglutaric acid imide; 3-Ethyl-3-phenyl-2,6-dioxopiperidine; 3-Ethyl-3-phenyl-2,6-piperidinedione; 3-Phenyl-3-ethyl-2,6-diketopiperidine; 3-Phenyl-3-ethyl-2,6-dioxopiperidine; 77-21-4; Gimid
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 217.26 Topological Polar Surface Area 46.2
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3487
PubChem SID
9692 ; 400159 ; 5047947 ; 7847598 ; 8152215 ; 10535494 ; 15414774 ; 26754495 ; 29215340 ; 29222619 ; 46506283 ; 48416061 ; 49973115 ; 53786842 ; 57321835 ; 78011658 ; 83568923 ; 92714692 ; 103304476 ; 104303656 ; 117423004 ; 124892162 ; 125357548 ; 126623946 ; 126679218 ; 128294734 ; 134338522 ; 134972155 ; 137141503 ; 137259869 ; 141622985 ; 144205194 ; 152037161 ; 160964704 ; 164831491 ; 170465223 ; 178103767 ; 179225784 ; 198993194 ; 223439844 ; 223681168 ; 226486312 ; 249990931 ; 250170659
ChEBI ID
CHEBI:5439
CAS Number
77-21-4
TTD Drug ID
D0Z9NZ
Formula
C13H15NO2
Canonical SMILES
CCC1(CCC(=O)NC1=O)C2=CC=CC=C2
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)
InChIKey
JMBQKKAJIKAWKF-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3-Phenyloxolan-2-one DM002133
23269
Unclear 1 [3]
4-hydroxy-2-ethyl-2-phenylglutarimide DM002132
162086
Oxidation - Hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001145 Glutethimide 4-hydroxy-2-ethyl-2-phenylglutarimide Oxidation - Hydroxylation Unclear [4]
MR001146 Glutethimide 3-Phenyloxolan-2-one Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Myeloperoxidase (MPO) DME0096 Homo sapiens
PERM_HUMAN
1.11.2.2
[2]
References
1 Glutethimide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Proteomic profile of aminoglutethimide-induced apoptosis in HL-60 cells: role of myeloperoxidase and arylamine free radicals. Chem Biol Interact. 2015 Sep 5;239:129-38.
3 Toxicity of alpha-phenyl-gamma-butyrolactone, a metabolite of glutethimide in human urine Res Commun Chem Pathol Pharmacol. 1977 Nov;18(3):439-51.
4 Synthesis of an active hydroxylated glutethimide metabolite and some related analogs with sedative-hypnotic and anticonvulsant properties J Med Chem. 1975 Jul;18(7):736-41. doi: 10.1021/jm00241a019.

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