GLUTETHIMIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H15NO2
Molecular Weight	217.2637
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCC1(CCC(=O)NC1=O)C2=CC=CC=C2

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

Molecular Formula	C13H15NO2
Molecular Weight	217.2637
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108	Primary		Approved 8,429	GLUTETHIMIDE

C_max

Value	Dose	Analyte	Population
4.34 μg/mL	500 mg single, oral	GLUTETHIMIDE plasma	Homo sapiens
5 μg/mL	500 mg single, oral	GLUTETHIMIDE plasma	Homo sapiens
6.5 μg/mL	1000 mg single, oral	GLUTETHIMIDE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
33.51 μg × h/mL	500 mg 3 times / day multiple, oral		GLUTETHIMIDE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.6 h			GLUTETHIMIDE serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
45.8%	500 mg single, oral		GLUTETHIMIDE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
4 g multiple, oral Overdose	unhealthy, 42	Disc. AE: Cerebellar ataxia...
10 g single, oral Overdose	unknown	Disc. AE: Coma...
15000 mg single, oral Overdose	healthy	Disc. AE: Unconsciousness, Uremia...

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AEs

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AE	Significance	Dose	Population
Cerebellar ataxia	severe Disc. AE	4 g multiple, oral Overdose	unhealthy, 42
Coma	grade 4-5 Disc. AE	10 g single, oral Overdose	unknown
Unconsciousness	grade 4 Disc. AE	15000 mg single, oral Overdose	healthy
Multiorgan failure	severe Disc. AE	15000 mg single, oral Overdose	healthy
Multiple congenital abnormalities	severe Disc. AE	15000 mg single, oral Overdose	healthy

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ChemIDplus	60490746	https://chem.nlm.nih.gov/chemidplus/id/0060490746
PubChem	133065417	https://pubchem.ncbi.nlm.nih.gov/compound/133065417
Wikidata	Q27270160

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PubMed

Show entries

Title	Date	PubMed
Anti-convulsant effect of phthalazino-2,3b-phthalazine-5(14H),12(7h)-dione (L-5418). I. Behavioral effect.	1978 Feb	565846
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	3626855

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Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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