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Hexobarbital

Catalog No. DB01355 Name DrugBank
CAS Number 56-29-1 Website http://www.ualberta.ca/
M. F. C12H16N2O3 Telephone (780) 492-3111
M. W. 236.26704 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1183

SYNONYMS

IUPAC name
5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
IUPAC Traditional name
hexobarbital
Brand Name
Sombulex
Sombucaps
Citopan
Evipan
Noctivane
Somnalert
Evipal
Cyclopan
Cyclopal
Barbidorm
Synonyms
5-(1-cyclohexen-1-yl)-1,5-dimethylbarbituric acid
Hexobarbitone
Methexenyl
Methylhexabital

DATABASE IDS

CAS Number 56-29-1

PROPERTIES

Hydrophobicity(logP) 1.98 [SANGSTER (1994)]

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A barbiturate that is effective as a hypnotic and sedative. [PubChem]
Indication For the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli.
Pharmacology Hexobarbital is a barbiturate derivative having hypnotic and sedative effects. It was used in the 1940s-1950s as an agent for inducing anesthesia for surgery and has a relatively fast onset of effects and short duration of action. However it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.
Toxicity Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Protein Binding 25%
References
Takenoshita R, Toki S: [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases] Yakugaku Zasshi. 2004 Dec;124(12):857-71. [Pubmed]
Wahlstrom G: A study of the duration of acute tolerance induced with hexobarbital in male rats. Pharmacol Biochem Behav. 1998 Apr;59(4):945-8. [Pubmed]
Korkmaz S, Ljungblad E, Wahlstrom G: Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat. Brain Res. 1995 Apr 10;676(2):371-7. [Pubmed]
Dall V, Orntoft U, Schmidt A, Nordholm L: Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. Pharmacol Biochem Behav. 1993 Sep;46(1):73-6. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Takenoshita R, Toki S: [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases] Yakugaku Zasshi. 2004 Dec;124(12):857-71. Pubmed
  • Wahlstrom G: A study of the duration of acute tolerance induced with hexobarbital in male rats. Pharmacol Biochem Behav. 1998 Apr;59(4):945-8. Pubmed
  • Korkmaz S, Ljungblad E, Wahlstrom G: Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat. Brain Res. 1995 Apr 10;676(2):371-7. Pubmed
  • Dall V, Orntoft U, Schmidt A, Nordholm L: Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. Pharmacol Biochem Behav. 1993 Sep;46(1):73-6. Pubmed