- Hexobarbital
-
Hexobarbital 
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 - 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)
Key:UYXAWHWODHRRMR-UHFFFAOYSA-N
(what is this?) (verify)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it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days. Hexobarbital was also marketed as a rapid-acting sleeping medication with short duration (tradenames: Citopan, Evipan and others, usually in 250 mg strength tablets). 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" (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.
Anesthetic: General anesthetics (N01A) Inhalation OthersInjection OthersHypnotics/Sedatives (N05C) GABAA Agonists/PAMs Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarbital • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenobarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital; Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lormetazepam • Midazolam • Nimetazepam • Nitrazepam • Quazepam • Temazepam • Triazolam; Carbamates: Carisoprodol • Ethinamate • Hexapropymate • Meprobamate • Methocarbamol • Procymate • Tybamate; Neuroactive Steroids: Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Eltanolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • Org 21465 • Tetrahydrodeoxycorticosterone; Nonbenzodiazepines: CL-218,872 • Eszopiclone • Indiplon • JM-1232 • Lirequinil • Necopidem • Pazinaclone • ROD-188 • Saripidem • Suproclone • Suriclone • SX-3228 • U-89843A • U-90042 • Zaleplon • Zolpidem • Zopiclone; Phenols: Fospropofol • Propofol; Piperidinediones: Glutethimide • Methyprylon • Pyrithyldione • Piperidione; Quinazolinones: Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone • Nitromethaqualone; Others: 2-Methyl-2-butanol • Acetophenone • Acetylglycinamide chloral hydrate • Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Centalun • Chloral hydrate • Chloralose • Chloralodol • Clomethiazole • Dichloralphenazone • Ethanol (Alcohol) • Ethchlorvynol • Etomidate • Gaboxadol • Loreclezole • Methylpentynol • Metomidate • Paraldehyde • Petrichloral • Sulfonmethane • Trichloroethanol • Triclofos • Valerenic acid (Valerian)GABAB Agonists H1 Inverse agonists Antihistamines: Captodiame • Cyproheptadine • Dimenhydrinate • Diphenhydramine • Doxylamine • Hydroxyzine • Methapyrilene • Pheniramine • Promethazine • Propiomazine; Others: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) • Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)α1-Adrenergic Antagonists Mianserin • Niaprazine • Trazodone; Others: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)α2-Adrenergic Agonists 4-NEMD • Clonidine • Detomidine • Dexmedetomidine • Lofexidine • Medetomidine • Romifidine • Tizanidine • Xylazine5-HT2A Antagonists Eplivanserin • Niaprazine • Pruvanserin • Trazodone • Volinanserin; Others: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) • Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)Melatonin Agonists Orexin Antagonists Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant • TCS-OX2-29Others Acecarbromal • Apronal • Bromisoval • Cannabidiol (Cannabis) • Carbromal • Embutramide • Evoxine • Fenadiazole • Gabapentin • Kavalactones (Kava) • Mephenoxalone • Opiates/Opioids (Hydrocodone, Morphine (Opium), etc.) • Passion flower • Scopolamine (Mandrake) • ValnoctamideCategories:- Barbiturates
- General anesthetics
- 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)
Wikimedia Foundation. 2010.
