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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
Structure of HEXOBARBITAL

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)

HIDE SMILES / InChI

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 ( + / - )

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Citopan

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
419 min
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
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
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
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
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
[New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases].
2004 Dec
Antiglucocorticoid RU38486 reduces net protein catabolism in experimental acute renal failure.
2005 Feb 17
Enantioselective gas chromatographic separation of racemic N-alkylated barbiturates: application of C11-Chirasil-Dex as chiral stationary phase in GC.
2007 Sep 18
Sir Ivan Magill KCVO, DSc, MB, BCh, BAO, FRCS, FFARCS (Hon), FFARCSI (Hon), DA, (1888-1986).
2008 Sep
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

3.571 to 7.142 mg/kg
Route of Administration: Intravenous
In Vitro Use Guide
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 Fri Dec 15 18:55:22 UTC 2023
Edited
by admin
on Fri Dec 15 18:55:22 UTC 2023
Record UNII
AL8Z8K3P6S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HEXOBARBITAL
EP   INN   JAN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
HEXOBARBITAL [EP IMPURITY]
Common Name English
hexobarbital [INN]
Common Name English
Hexobarbital [WHO-DD]
Common Name English
HEXOBARBITAL CIII
USP-RS  
Common Name English
HEXOBARBITAL [MART.]
Common Name English
NSC-71929
Code English
HEXOBARBITAL [VANDF]
Common Name English
HEXOBARBITAL [MI]
Common Name English
HEXOBARBITAL [JAN]
Common Name English
5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbituric acid
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
WHO-VATC QN01AF02
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
WHO-VATC QN05CA16
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
WHO-ATC N01AF02
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
WHO-ATC N05CA16
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
Code System Code Type Description
SMS_ID
100000083979
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-264-9
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
CAS
56-29-1
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
MESH
D006591
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
PUBCHEM
3608
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
RXCUI
5302
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
HEXOBARBITAL
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
NCI_THESAURUS
C77630
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
INN
2086
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
NSC
71929
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
CHEBI
5706
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL7728
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
FDA UNII
AL8Z8K3P6S
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
DRUG BANK
DB01355
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
DRUG CENTRAL
1369
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
MERCK INDEX
m6010
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID9023122
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
EVMPD
SUB08038MIG
Created by admin on Fri Dec 15 18:55:22 UTC 2023 , Edited by admin on Fri Dec 15 18:55:22 UTC 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY