Hexobarbital
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| Systematic (IUPAC) name | |
| (RS)-5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Pharmacokinetic data | |
| Protein binding | 25% |
| Identifiers | |
| CAS number | 56-29-1  50-09-9 (sodium salt) |
| ATC code | N01AF02 N05CA16 |
| PubChem | CID 3608 |
| DrugBank | EXPT03301 |
| ChemSpider | 3482 |
| UNII | AL8Z8K3P6S |
| KEGG | D01071 |
| ChEBI | CHEBI:5706 |
| ChEMBL | CHEMBL7728 |
| Chemical data | |
| Formula | C12H16N2O3 |
| Mol. mass | 236.267 g/mol |
| SMILES | eMolecules & PubChem |
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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it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.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.
[edit] Further reading
- Takenoshita, R.; Toki, S. (2004). "New aspects of hexobarbital metabolism: Stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases" (in japanese) (pdf). Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 124 (12): 857–871. doi:10.1248/yakushi.124.857. PMID 15577260. http://www.jstage.jst.go.jp/article/yakushi/124/12/857/_pdf.
- 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. 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. 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. PMID 8255925.
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