Hexobarbital

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Hexobarbital
Systematic (IUPAC) name
200px
(RS)-5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
Pharmacokinetic data
Protein binding	25%

Identifiers
CAS Number	56-29-1 50-09-9 (sodium salt)
ATC code	N01AF02 (WHO) N05CA16
PubChem	CID 3608
DrugBank	EXPT03301
ChemSpider	5545
Chemical data
Formula	C₁₂H₁₆N₂O₃
Molar mass	236.267 g/mol[[Script error: No such module "String".]]
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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it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.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.

Takenoshita R, Toki S (2004). "[New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases]". Yakugaku Zasshi. 124 (12): 857–71. 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". Pharmacol Biochem Behav. 59 (4): 945–8. 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 Res. 676 (2): 371–7. 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". Pharmacol Biochem Behav. 46 (1): 73–6. doi:10.1016/0091-3057(93)90319-O. PMID 8255925.

v t e GABA_A receptor positive allosteric modulators
Barbiturates	Allobarbital • Alphenal • Amobarbital • Aprobarbital • Barbexaclone • Barbital • Benzobarbital • Benzylbutylbarbiturate • Brallobarbital • Brophebarbital • Bucolome • Butabarbital • Butalbital • Butobarbital • Butallylonal • Carbubarb • Crotylbarbital • Cyclobarbital • Cyclopal • Enallylpropymal • Ethallobarbital • Febarbamate • Heptabarbital • Hexethal • Hexobarbital • Mephobarbital • Metharbital • Methohexital • Methylphenobarbital • Narcobarbital • Nealbarbital • Pentobarbital • Phenobarbital • Phetharbital • Primidone • Prazitone • Probarbital • Propallylonal • Proxibarbal • Proxibarbital • Reposal • Secbutabarbital • Secobarbital • Sigmodal • Spirobarbital • Talbutal • Thialbarbital • Thiamylal • Thiobarbital • Thiobutabarbital • Thiopental • Valofane • Vinbarbital • Vinylbital
Benzodiazepines	Adinazolam • Alprazolam • Arfendazam • Avizafone • Bentazepam • Bretazenil • Bromazepam • Brotizolam • Camazepam • Chlordiazepoxide • Ciclotizolam • Cinolazepam • Clazolam • Climazolam • Clobazam • Clonazepam • Clorazepate • Clotiazepam • Cloxazolam • Cyprazepam • Delorazepam • Diazepam • Doxefazepam • Elfazepam • Estazolam • Ethyl carfluzepate • Ethyl dirazepate • Ethyl loflazepate • Etizolam • Fletazepam • Fludiazepam • Flunitrazepam • Flurazepam • Flutazolam • Flutemazepam • Flutoprazepam • Fosazepam • Gidazepam • Girisopam • Halazepam • Haloxazolam • Iclazepam • Imidazenil • Ketazolam • Lofendazam • Lopirazepam • Lopirazepam • Loprazolam • Lorazepam • Lormetazepam • Meclonazepam • Medazepam • Menitrazepam • Metaclazepam • Mexazolam • Midazolam • Nerisopam • Nimetazepam • Nitrazepam • Nitrazepate • Nordazepam • Oxazepam • Oxazolam • Phenazepam • Pinazepam • Pivoxazepam • Prazepam • Premazepam • Proflazepam • QH-II-66 • Quazepam • Reclazepam • Remimazolam • Rilmazafone • Ripazepam • Ro48-6791 • SH-053-R-CH3-2′F • Sulazepam • Temazepam • Tetrazepam • Tofisopam • Triazolam • Triflubazam • Uldazepam • Zapizolam • Zolazepam • Zomebazam
Carbamates	Carisbamate • Carisoprodol • Emylcamate • Ethinamate • Febarbamate • Felbamate • Hexapropymate • Mebutamate • Meprobamate • Methocarbamol • Phenprobamate • Procymate • Styramate • Tybamate
Neuroactive steroids	Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • THDOC
Nonbenzodiazepines	Abecarnil • Adipiplon • Alpidem • CGS-20625 • CGS-9896 • CL-218,872 • ELB-139 • Eszopiclone • Fasiplon • Gedocarnil • Indiplon • L-838,417 • Necopidem • NS-2664 • NS-2710 • Ocinaplon • Pagoclone • Panadiplon • Pazinaclone • Pipequaline • ROD-188 • RWJ-51204 • Saripidem • SB-205,384 • SL-651,498 • Suproclone • Suriclone • SX-3228 • Taniplon • TP-003 • TPA-023 • TP-13 • U-89843A • U-90042 • Y-23684 • Zaleplon • Zolpidem • Zopiclone
Phenols	Fospropofol • Propofol • Thymol
Piperidinediones	Glutethimide • Methyprylon • Piperidione • Pyrithyldione
Pyrazolopyridines	Cartazolate • Etazolate • ICI-190,622 • Tracazolate
Quinazolinones	Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone
Volatiles/gases	2-Methyl-2-butanol • Acetone • Acetophenone • Acetylglycinamide chloral hydrate • Benzene • Butane • Butanol • Butylene • Centalun • Chloral • Chloral hydrate • Chlorobutanol • Chloroform • Cyclopropane • Desflurane • Dichloromethane • Diethyl ether • Enflurane • Ethanol (Alcohol) • Ethyl chloride • Ethylene • Gasoline • Halothane • Isoflurane • Kerosine • Menthol • Methanol • Methoxyflurane • Methoxypropane • Methylbutanol • Nitric oxide • Nitrogen • Nitrous oxide • Paraldehyde • Pentanol • Propane • Propanol • Propylene • Sevoflurane • Toluene • Trichloroethanol • Trichloroethylene • Vinyl ether • Xenon
Others	Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralodol • Chloralose • Chlormezanone • Clomethiazole • DEABL • Ethchlorvynol • Etifoxine • Etomidate • GABA • Kavalactones (Kava-kava) • Loreclezole • Methylpentynol • Petrichloral • Propanidid • Skullcap • Stiripentol • Sulfonmethane • Tetronal • Triclofos • Trional • Valeric acid, Valerenic acid (Valerian)

Anesthetic: General anesthetics (N01A)

Inhalation

Ethers	Diethyl ether • Methoxypropane • Vinyl ether • halogenated ethers (Desflurane • Enflurane • Isoflurane • Methoxyflurane • Sevoflurane)
Haloalkanes	Chloroform • Halothane^# • Trichloroethylene
Others	Cyclopropane • Ethylene • Nitrous oxide^# • Xenon

Injection

Barbiturates	Hexobarbital • Methohexital • Narcobarbital • Thiopental^#
Opioids	Alfentanil • Anileridine • Fentanyl • Phenoperidine • Remifentanil • Sufentanil
Neuroactive steroids	Alfaxalone • Minaxolone
Others	Droperidol • Etomidate • Fospropofol • gamma-Hydroxybutyric acid • Ketamine^# /Esketamine • Midazolam • Propanidid • Propofol

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: CNS

anat(s,m,p,4,e,b,d,c,a,f,l,g)/phys/devp/cell

noco(m,d,e,h,v,s)/cong/tumr,sysi/epon,injr

proc,drug(N1A/2AB/C/3/4/7A/B/C/D)

Hypnotics/Sedatives (N05C)

GABA_A receptor

Barbiturates

Ultrashort-acting	Methohexital • Thiamylal • Thiopental
Short/intermediate- acting	Allobarbital • Amobarbital • Butabarbital • Butobarbital • Pentobarbital • Secobarbital • Talbutal
Long-acting	Barbital • Mephobarbital • Phenobarbital
Ungrouped	Cyclobarbital • Ethallobarbital • Heptabarbital • Hexobarbital • Proxibarbal • Reposal • Vinylbital • Vinbarbital

Benzodiazepines

Short-acting	Brotizolam • Cinolazepam • Doxefazepam • Loprazolam • Midazolam • Triazolam
Intermediate-acting	Estazolam • Flunitrazepam • Lormetazepam • Nimetazepam • Temazepam
Long-acting	Flurazepam • Flutoprazepam • Nitrazepam • Quazepam

Dialkylphenols

Fospropofol • Propofol • Thymol

Nonbenzo-
diazepines

CL-218,872 • Eszopiclone • Indiplon • Lirequinil • Necopidem • Pazinaclone • ROD-188 • Saripidem • Suproclone • Suriclone • SX-3228 • U-89843A • U-90042 • Zaleplon • Zolpidem • Zopiclone

Piperidinediones

Glutethimide • Methyprylon • Pyrithyldione • Piperidione

Quinazolinones

Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone

Neuroactive
steroids

Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Eltanolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • Org 21465 • Tetrahydrodeoxycorticosterone

Alpha-2 adrenergic
receptor

Alpha-adrenergic agonists	4-NEMD • Clonidine • Dexmedetomidine • Lofexidine • Medetomidine • Romifidine • Tizanidine • Xylazine

Melatonin receptor

Melatonin	Agomelatine • Melatonin • Ramelteon • Tasimelteon

Histamine receptor &
Acetylcholine receptor

Antihistamines & Anticholinergics	Amitriptyline • Dimenhydrinate • Doxylamine • Hydroxyzine • Diphenhydramine • Bromodiphenhydramine • Carbinoxamine • Doxepin • Esmirtazapine • Orphenadrine • Mianserin • Mirtazapine • Phenyltoloxamine • Propiomazine • Pyrilamine • Scopolamine