Hexobarbital

Hexobarbital

Systematic (IUPAC) name
(RS)-5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
Clinical data
Legal status	?
Pharmacokinetic data
Protein binding	25%
Identifiers
CAS number	56-29-1 Y 50-09-9 (sodium salt)
ATC code	N01AF02 N05CA16
PubChem	CID 3608
DrugBank	DB01355
ChemSpider	3482 Y
UNII	AL8Z8K3P6S Y
KEGG	D01071 Y
ChEBI	CHEBI:5706 Y
ChEMBL	CHEMBL7728 Y
Chemical data
Formula	C12H16N2O3
Mol. mass	236.267 g/mol
SMILES O=C1N(C(=O)NC(=O)C1(/C2=C/CCCC2)C)C
InChI 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) Y Key:UYXAWHWODHRRMR-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Hexobarbital (as known in the U.S.A.), or hexobarbitone (as known elsewhere), sold both in acid and sodium salt forms as Citopan, Evipan, and Tobinal (usually in 250-mgm. strength tablets), is a barbiturate derivative having hypnotic and sedative effects. It was used in the 1940s-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. 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it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine; usually thiopental would be the barbiturate of choice for this application these days. Hexobarbital is still used in some scientific research.

Further reading

• Takenoshita, R.; Toki, S. (2004). "New aspects of hexobarbital metabolism: Stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases" (pdf). Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan (in japanese) 124 (12): 857–871. doi:10.1248/yakushi.124.857. PMID 15577260. 

• Wahlström, G. (1998). "A study of the duration of acute tolerance induced with hexobarbital in male rats". Pharmacology, Biochemistry, and Behavior 59 (4): 945–948. doi:10.1016/S0091-3057(97)00543-1. PMID 9586853. 

• Korkmaz, S.; Ljungblad, E.; Wahlström, G. (1995). "Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat". Brain Research 676 (2): 371–377. doi:10.1016/0006-8993(95)00132-A. PMID 7614008. 

• Dall, V.; Orntoft, U.; Schmidt, A.; Nordholm, L. (1993). "Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital". Pharmacology, Biochemistry, and Behavior 46 (1): 73–76. doi:10.1016/0091-3057(93)90319-O. PMID 8255925.