Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H16N2O3 |
Molecular Weight | 236.267 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(=O)NC(=O)C(C)(C1=O)C2=CCCCC2
InChI
InChIKey=UYXAWHWODHRRMR-UHFFFAOYSA-N
InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)
Molecular Formula | C12H16N2O3 |
Molecular Weight | 236.267 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.drugbank.ca/drugs/DB01355Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/citopam.html | https://www.ncbi.nlm.nih.gov/pubmed/2458634 | https://www.ncbi.nlm.nih.gov/pubmed/7965056
Sources: https://www.drugbank.ca/drugs/DB01355
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/citopam.html | https://www.ncbi.nlm.nih.gov/pubmed/2458634 | https://www.ncbi.nlm.nih.gov/pubmed/7965056
Hexobarbital or hexobarbitone, (sold both in acid and sodium salt, brand name Evipan, and Tobinal), is a barbiturate derivative having hypnotic and sedative effects. It was used in the 1940s and 1950s as an agent for inducing anesthesia for surgery, as well as a rapid-acting, short-lasting hypnotic for general use, and has a relatively fast onset of effects and short duration of action. It was also used to murder women prisoners at Ravensbruck Concentration Camp. Modern barbiturates (such as Thiopental) has largely supplanted the use of hexobarbital as an anesthetic, as they allow for better control of the depth of anesthesia. Hexobarbital is still used in some scientific research. Hexobarbital binds at a distinct binding site associated with a Cl- ionophore at the GABA-A receptor, increasing the duration of time for which the Cl- ionophore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7965056 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4692611 |
Primary | Citopan Approved UseUnknown |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
419 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164825/ |
2.97 mg/kg single, intravenous dose: 2.97 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
HEXOBARBITAL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
376 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164825/ |
4.1 mg/kg single, intravenous dose: 4.1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
HEXOBARBITAL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
261 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164825/ |
7.32 mg/kg single, intravenous dose: 7.32 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
HEXOBARBITAL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
490 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164825/ |
7.32 mg/kg single, intravenous dose: 7.32 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
HEXOBARBITAL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. | 1993 Sep |
|
Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat. | 1995 Apr 10 |
|
Pentobarbital decreases the gamma-aminobutyric acidA receptor subunit gamma-2 long/short mRNA ratio by a mechanism distinct from receptor occupation. | 1997 Oct |
|
A study of the duration of acute tolerance induced with hexobarbital in male rats. | 1998 Apr |
|
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection. | 2009 Jun |
|
Detection of ubiquityl-calmodulin conjugates with a novel high-molecular weight ubiquitylprotein-isopeptidase in rabbit tissues. | 2010 Oct 25 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2458634
Membranes were incubated with [35S]TBPS in 10 mM Na, K-phosphate buffer at 21°C for 60 min, in the presence or absence of Hexobarbital except for experiments on anion and cation effects. The reaction was terminated by filtration through a Whatman GF/B filter presoaked in 0.05% polyethyleneimine (so as to reduce [gammaS]TBPS binding to the filter) and washing twice with 5 ml of buffer solution. Specific [35S]TBPS binding was obtained by subtracting nonspecific binding obtained in the presence of 10 mkM gamma-BHC from total binding.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:55:22 GMT 2023
by
admin
on
Fri Dec 15 18:55:22 GMT 2023
|
Record UNII |
AL8Z8K3P6S
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C67084
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
||
|
WHO-VATC |
QN01AF02
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
||
|
WHO-VATC |
QN05CA16
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
||
|
WHO-ATC |
N01AF02
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
||
|
WHO-ATC |
N05CA16
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000083979
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
200-264-9
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
56-29-1
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
D006591
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
3608
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
5302
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | RxNorm | ||
|
HEXOBARBITAL
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
C77630
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
2086
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
71929
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
5706
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
CHEMBL7728
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
AL8Z8K3P6S
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
DB01355
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
1369
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
m6010
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID9023122
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY | |||
|
SUB08038MIG
Created by
admin on Fri Dec 15 18:55:22 GMT 2023 , Edited by admin on Fri Dec 15 18:55:22 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |