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Details

Stereochemistry RACEMIC
Molecular Formula C13H15NO2
Molecular Weight 217.2642
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUTETHIMIDE

SMILES

CCC1(CCC(=NC1=O)O)c2ccccc2

InChI

InChIKey=JMBQKKAJIKAWKF-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.drugbank.ca/drugs/DB01437 | https://www.ncbi.nlm.nih.gov/pubmed/2549762 | https://www.ncbi.nlm.nih.gov/pubmed/14193389

Glutethimide is a GABA agonist that was introduced by Ciba 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. Glutethimide was discontinued in the US by manufacturers in 1993. Current production levels in the United States point to it only being used in small-scale research.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GLUTETHIMIDE

Approved Use

Unknown

Launch Date

2.15308796E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.34 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTETHIMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
5 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTETHIMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
6.5 μg/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTETHIMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
33.51 μg × h/mL
500 mg 3 times / day multiple, oral
dose: 500 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GLUTETHIMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.6 h
GLUTETHIMIDE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
45.8%
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLUTETHIMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
4 g multiple, oral (max)
Overdose
Dose: 4 g
Route: oral
Route: multiple
Dose: 4 g
Sources: Page: p.561
unhealthy, 42
n = 1
Health Status: unhealthy
Condition: alcohol addiction
Age Group: 42
Sex: F
Population Size: 1
Sources: Page: p.561
Disc. AE: Cerebellar ataxia...
AEs leading to
discontinuation/dose reduction:
Cerebellar ataxia (severe)
Sources: Page: p.561
10 g single, oral (min)
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown
Health Status: unknown
Sources:
Disc. AE: Coma...
AEs leading to
discontinuation/dose reduction:
Coma (grade 4-5)
Sources:
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources: Page: p.72, 74
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources: Page: p.72, 74
Disc. AE: Unconsciousness, Uremia...
AEs leading to
discontinuation/dose reduction:
Unconsciousness (grade 4)
Uremia (severe)
Multiorgan failure (severe)
Multiple congenital abnormalities (severe)
Sources: Page: p.72, 74
AEs

AEs

AESignificanceDosePopulation
Cerebellar ataxia severe
Disc. AE
4 g multiple, oral (max)
Overdose
Dose: 4 g
Route: oral
Route: multiple
Dose: 4 g
Sources: Page: p.561
unhealthy, 42
n = 1
Health Status: unhealthy
Condition: alcohol addiction
Age Group: 42
Sex: F
Population Size: 1
Sources: Page: p.561
Coma grade 4-5
Disc. AE
10 g single, oral (min)
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown
Health Status: unknown
Sources:
Unconsciousness grade 4
Disc. AE
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources: Page: p.72, 74
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources: Page: p.72, 74
Multiorgan failure severe
Disc. AE
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources: Page: p.72, 74
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources: Page: p.72, 74
Multiple congenital abnormalities severe
Disc. AE
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources: Page: p.72, 74
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources: Page: p.72, 74
Uremia severe
Disc. AE
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources: Page: p.72, 74
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources: Page: p.72, 74
PubMed

PubMed

TitleDatePubMed
Neurological effects of glutethimide.
1968 Dec
[Hypocalcemic seizures after misuse of glutethimide (Doriden)].
1976 May 10
Anti-convulsant effect of phthalazino-2,3b-phthalazine-5(14H),12(7h)-dione (L-5418). I. Behavioral effect.
1978 Feb
Catatonia associated with glutethimide withdrawal.
1983 Jan
Lack of correlation between plasma 4-hydroxyglutethimide and severity of coma in acute glutethimide poisoning. A case report and brief review of the literature.
1987 Jul-Aug
Patents

Sample Use Guides

Usual adult dose: 500 mg at bedtime; dose may be repeated if necessary, but not less than four hours before patient arises
Route of Administration: Oral
Chick embryo liver cells (CELCs) and chicken hepatoma cell line (LMH) were used to evaluate 5-Aminolevulinic acid synthase (ALA synthase) activity. CELCs and LMH cells were treated with Glutethimide (50mkM) or Glutethimide (50mkM)+ 4,6-dioxoheptanoic acid (0-500mkM)) and maintained for 18 h, after which cells were harvested, sonicates prepared and used to measure ALA synthase activity. The combination of glutethimide and DHA synergistically increased ALA synthase activity in both CELCs and LMH cells
Name Type Language
GLUTETHIMIDE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
GLUTETHIMIDE [MART.]
Common Name English
GLUTETHIMIDE [VANDF]
Common Name English
GLUTETHIMIDE [MI]
Common Name English
2-ETHYL-2-PHENYLGLUTARIMIDE
Systematic Name English
DORIDEN
Brand Name English
2,6-PIPERIDINEDIONE, 3-ETHYL-3-PHENYL-
Systematic Name English
ELRODORM
Common Name English
NOXYRON
Common Name English
GLUTETHIMIDE [INN]
Common Name English
GLUTETHIMIDE [JAN]
Common Name English
NSC-95239
Code English
GLUTETHIMIDE [ORANGE BOOK]
Common Name English
RIGENOX
Common Name English
GLUTETHIMIDE [HSDB]
Common Name English
SARODORMIN
Common Name English
GLUTETHIMIDE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29756
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
DEA NO. 2550
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
WHO-VATC QN05CE01
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
WHO-ATC N05CE01
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
Code System Code Type Description
MESH
D005984
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-012-0
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
DRUG CENTRAL
1313
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
INN
484
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
RXCUI
4903
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY RxNorm
PUBCHEM
3487
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
HSDB
3088
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL1102
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
MERCK INDEX
M5783
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY Merck Index
FDA UNII
C8I4BVN78E
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
IUPHAR
7192
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
WIKIPEDIA
GLUTETHIMIDE
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
NCI_THESAURUS
C65807
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
EVMPD
SUB07945MIG
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
CAS
77-21-4
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
DRUG BANK
DB01437
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY
EPA CompTox
77-21-4
Created by admin on Sat Jun 26 10:20:21 UTC 2021 , Edited by admin on Sat Jun 26 10:20:21 UTC 2021
PRIMARY