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

• ChemBase ID: 1244
• Molecular Formular: C13H15NO2
• Molecular Mass: 217.2637
• Monoisotopic Mass: 217.11027873
• SMILES: O=C1NC(=O)CCC1(CC)c1ccccc1
• Canonical SMILES: CCC1(CCC(=O)NC1=O)c1ccccc1
• 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)
• InChIKey: JMBQKKAJIKAWKF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-3-phenylpiperidine-2,6-dione
• IUPAC Traditional name: glutethimide; 2-ethyl-2-phenylglutarimide
• Brand Name: Sarodormin; Doriden; Elrodorm; Alfimid; Noxiron; Noxyron; Ondasil; Rigenox; Glimid; Gimid
• Synonyms: Glutethimide; Gluthetimide; Glutathimid; Glutethimid; Glutetimid; Glutetimide; Glutethimide; 3-乙基-3-苯基-2,6-哌啶二酮; 格鲁米特

Database IDs

• CAS Number: 77-21-4
• EC Number: 201-012-0
• MDL Number: MFCD00056091
• PubChem SID: 160964704; 46506283
• PubChem CID: 3487
• ATC CODE: N05CE01
• CHEMBL: 1102
• Chemspider ID: 3367
• DrugBank ID: DB01437
• KEGG ID: D00532
• Unique Ingredient Identifier: C8I4BVN78E
• Wikipedia Title: Glutethimide

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.691995
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.12847
• LogD (pH = 7.4): 2.1284485
• Log P: 2.1284704
• Molar Refractivity: 60.6539 cm^3
• Polarizability: 23.766676 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.89
• LOG S: -2.82
• Solubility (Water): 3.27e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.999 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): 1.90 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: MA4725000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: oral
• Bioavailability: Variable
• Excretion: Renal:2% Fecal:2%
• Half Life: 10-12 hours
• Metabolism: Hepatic
• Legal Status: ; Schedule III international; Schedule II (US)
• Pregnancy Category: C: (United States)

DETAILS

DrugBank - DB01437

• Drug Groups: illicit; approved
• Description: A hypnotic and sedative. Its use has been largely superseded by other drugs. [PubChem]
• Indication: For the treatment of insomnia.
• Pharmacology: Glutethimide is a hypnotic sedative that was introduced in 1954 as a safe alternative to barbiturates to treat insomnia. Before long, however, it had become clear that glutethimide was just as likely to cause addiction and caused similarly severe withdrawal symptoms.
• Toxicity: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Glutethimide is almost completely metabolized.
• Absorption: Variable
• Half Life: 10-12 hours
• 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.
• External Links: Wikipedia