Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C13H15NO2.H2O |
| Molecular Weight | 235.279 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CCC1(CCC(=O)NC1=O)C2=CC=CC=C2
InChI
InChIKey=UIIRXSRRFRGPPE-UHFFFAOYSA-N
InChI=1S/C13H15NO2.H2O/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);1H2
| Molecular Formula | C13H15NO2 |
| Molecular Weight | 217.2637 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.34 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5568259/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
33.51 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/902458/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.6 h |
GLUTETHIMIDE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
45.8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5568259/ |
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
| Dose | Population | Adverse 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 |
unknown |
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) Sources: Page: p.72, 74Uremia (severe) Multiorgan failure (severe) Multiple congenital abnormalities (severe) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
unknown |
| 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
| Title | Date | PubMed |
|---|---|---|
| Neurological effects of glutethimide. | 1968 Dec |
|
| 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 |
|
| Glutethimide intoxication and withdrawal. | 1988 Apr |
|
| Mechanism of iron potentiation of hepatic uroporphyria: studies in cultured chick embryo liver cells. | 1989 Sep |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:27:34 GMT 2023
by
admin
on
Sat Dec 16 10:27:34 GMT 2023
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| Record UNII |
8C221G270E
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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60490-74-6
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133065417
Created by
admin on Sat Dec 16 10:27:34 GMT 2023 , Edited by admin on Sat Dec 16 10:27:34 GMT 2023
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |