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
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 Overdose |
unhealthy, 42 |
Disc. AE: Cerebellar ataxia... AEs leading to discontinuation/dose reduction: Cerebellar ataxia (severe) Sources: |
10 g single, oral 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: |
healthy |
Disc. AE: Unconsciousness, Uremia... AEs leading to discontinuation/dose reduction: Unconsciousness (grade 4) Sources: Uremia (severe) Multiorgan failure (severe) Multiple congenital abnormalities (severe) |
AEs
| 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 Dose: 15000 mg Route: oral Route: single Dose: 15000 mg Sources: |
healthy |
| Multiorgan failure | severe Disc. AE |
15000 mg single, oral Overdose Dose: 15000 mg Route: oral Route: single Dose: 15000 mg Sources: |
healthy |
| Multiple congenital abnormalities | severe Disc. AE |
15000 mg single, oral Overdose Dose: 15000 mg Route: oral Route: single Dose: 15000 mg Sources: |
healthy |
| Uremia | severe Disc. AE |
15000 mg single, oral Overdose Dose: 15000 mg Route: oral Route: single Dose: 15000 mg Sources: |
healthy |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes. | 2003-03 |
|
| Mechanism of iron potentiation of hepatic uroporphyria: studies in cultured chick embryo liver cells. | 1989-09 |
|
| Glutethimide intoxication and withdrawal. | 1988-04 |
|
| Lack of correlation between plasma 4-hydroxyglutethimide and severity of coma in acute glutethimide poisoning. A case report and brief review of the literature. | 1987-07-01 |
|
| Catatonia associated with glutethimide withdrawal. | 1983-01 |
|
| Anti-convulsant effect of phthalazino-2,3b-phthalazine-5(14H),12(7h)-dione (L-5418). I. Behavioral effect. | 1978-02 |
|
| [Hypocalcemic seizures after misuse of glutethimide (Doriden)]. | 1976-05-10 |
|
| Neurological effects of glutethimide. | 1968-12 |
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
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60490-74-6
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133065417
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ACTIVE MOIETY
SUBSTANCE RECORD
