メトヘキシタール
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/08/12 23:27:44」(JST)
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Methohexital
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| Systematic (IUPAC) name |
| 5-hex-3-yn-2-yl-1- methyl-5-prop-2-enyl-1, 3-diazinane-2,4,6-trione |
| Clinical data |
| AHFS/Drugs.com |
Consumer Drug Information |
| Pregnancy cat. |
B (USA) |
| Legal status |
Prescription Only (S4) (AU) Schedule IV |
| Routes |
Intravenous, rectal |
| Pharmacokinetic data |
| Bioavailability |
I.V. ~100%
Rectal ~17% |
| Metabolism |
Hepatic |
| Half-life |
5.6 ± 2.7 minutes |
| Excretion |
? |
| Identifiers |
| CAS number |
151-83-7 Y |
| ATC code |
N01AF01 N05CA15 |
| PubChem |
CID 9034 |
| DrugBank |
DB00474 |
| ChemSpider |
8683 Y |
| UNII |
E5B8ND5IPE Y |
| KEGG |
D04985 Y |
| ChEBI |
CHEBI:102216 Y |
| ChEMBL |
CHEMBL7413 Y |
| Chemical data |
| Formula |
C14H18N2O3 |
| Mol. mass |
262.304 |
SMILES
- O=C1N(C(=O)NC(=O)C1(C\C=C)C(C#CCC)C)C
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InChI
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InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19) Y
Key:NZXKDOXHBHYTKP-UHFFFAOYSA-N Y
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Y (what is this?) (verify)
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Methohexital or methohexitone, (marketed under the brand name Brevital) is a drug which is a barbiturate derivative. It is classified as short-acting, and has a rapid onset of action. It is similar in its effects to sodium thiopental, a drug with which it competed in the market for anaesthetics.
Contents
- 1 Pharmacology
- 2 Indications
- 3 Chemistry
- 4 References
- 5 External links
Pharmacology[edit source | edit]
Methohexital binds to a distinct site which is associated with Cl− ionophores at GABAA receptors.[1] This increases the length of time which the Cl− ionopores are open, thus causing an inhibitory effect.
Metabolism of methohexital is primarily hepatic (i.e., taking place in the liver) via demethylation and oxidation.[citation needed] Side-chain oxidation is the primary means of metabolism involved in the termination of the drug's biological activity.
Protein binding is approximately 73% for methohexital.[citation needed]
Indications[edit source | edit]
Methohexital is primarily used to induce anesthesia, and is generally provided as a sodium salt (i.e. methohexital sodium). It is only used in hospital or similar settings, under strict supervision.[citation needed] It has been commonly used to induce deep sedation, "twilight sleep" or general anesthesia for oral surgery and dentistry. It is also used to induce anesthesia prior to ECT (electroconvulsive therapy).
Chemistry[edit source | edit]
Methohexital, 5-allyl-1-methyl-5-(1-methyl-2-pentinyl barbituric acid, is synthesized in the classic manner of making barbituric acid derivatives, in particular by the reaction of malonic ester derivatives with derivatives of urea. The resulting allyl-(1-methyl-2-pentynyl) malonic ester is synthesized by subsequent alkylation of the malonic ester itself, beginning with 2-bromo-3-hexyne, which gives (1-methyl-2-pentynyl)malonic ester, and then by allylbromide. In the final step, reaction of the disubstituted malonic ester with N-methylurea gives desired methohexital.
W.J. Doran, U.S. Patent 2,872,448 (1959).
References[edit source | edit]
- ^ Katzung, Bertram G., Basic and Clinical Pharmacology, 10th ed., p. 406-407
External links[edit source | edit]
- RxList.com - Methohexital
- Drugs.com - Methohexital Sodium
- DrugLib.com - Brevital (Methohexital Sodium)
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Anesthesia (outline)
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| Types |
- General (Twilight)
- Local (Topical)
- Spinal
- Epidural
- Dental (Inferior alveolar nerve)
- Neuroleptanalgesic anesthesia
- Brachial plexus block
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| Techniques |
- Airway management
- Anesthesia provision in the US
- Capnography
- Concentration effect
- Dogliotti's principle
- Drug-induced amnesia
- Fink effect
- Intraoperative neurophysiological monitoring
- Penthrox inhaler
- Tracheal intubation
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| Measurements |
- ASA physical status classification system
- Baricity
- Bispectral index
- Direct Fick method
- Entropy monitoring
- Fick principle
- Goldman index
- Guedel's classification
- Mallampati score
- Minimum alveolar concentration
- Neuromuscular monitoring
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| Instruments |
- Anaesthetic machine
- Anesthesia cart
- Boyle's machine
- Gas cylinder
- Laryngeal mask airway
- Laryngeal tube
- Medical monitor
- Odom's indicator
- Relative analgesia machine
- Vaporiser
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| Drugs |
- Benzodiazepine
- Etomidate
- General anaesthetic
- Inhalational anaesthetic
- Infiltration analgesia
- Ketamine
- Local anesthetic
- Methohexital
- Methoxyflurane
- Midazolam
- Neuraxial blockade
- Propofol
- Thiopental
- Thiopentone
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| Complications |
- Emergence delirium
- Allergic reactions
- Anesthesia awareness
- Local anesthetic toxicity
- Malignant hyperthermia
- Perioperative mortality
- Postanesthetic shivering
- Postoperative nausea and vomiting
- Postoperative residual curarization
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| Fields of study |
- Cardiothoracic
- Geriatric
- Oral sedation dentistry
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| Professions |
- Anesthesiologist
- Anesthesiologist assistant
- Nurse anesthetist
- Operating Department Practitioners
- Certified Anesthesia Technician
- Certified Anesthesia Technologist
- Anaesthetic technician
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| History |
- A.C.E. mixture
- Helsinki Declaration for Patient Safety in Anaesthesiology
- History of general anesthesia
- History of neuraxial anesthesia
- History of tracheal intubation
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| Organizations |
- American Association of Nurse Anesthetists
- American Society of Anesthesia Technologists & Technicians
- American Society of Anesthesiologists
- Anaesthesia Trauma and Critical Care
- Association of Anaesthetists of Great Britain and Ireland
- Association of Veterinary Anaesthetists
- Australian and New Zealand College of Anaesthetists
- Australian Society of Anaesthetists
- International Anesthesia Research Society
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Anesthetic: General anesthetics (N01A)
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| Inhalation |
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Ethers
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- Diethyl ether
- Methoxypropane
- Vinyl ether
- halogenated ethers
- Desflurane
- Enflurane
- Isoflurane
- Methoxyflurane
- Sevoflurane
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Haloalkanes
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- Chloroform
- Halothane#
- Trichloroethylene
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Others
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- Cyclopropane
- Ethylene
- Nitrous oxide#
- Xenon
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| Injection |
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Barbiturates
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- Hexobarbital
- Methohexital
- Narcobarbital
- Thiopental#
- Thiotetrabarbital
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Opioids
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- Alfentanil
- Anileridine
- Fentanyl
- Phenoperidine
- Remifentanil
- Sufentanil
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Neuroactive steroids
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Others
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- Droperidol
- Etomidate
- Fospropofol
- gamma-Hydroxybutyric acid
- Ketamine# /Esketamine
- Midazolam
- Propanidid
- Propofol
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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anat (n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp
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noco (m/d/e/h/v/s)/cong/tumr, sysi/epon, injr
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proc, drug (N1A/2AB/C/3/4/7A/B/C/D)
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Hypnotics/sedatives (N05C)
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GABAA
agonists/PAMs |
Alcohols: 2M2B • Chloralodol • Ethanol (Alcohol) • Ethchlorvynol • Methylpentynol • Trichloroethanol
Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarb • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenallymal • Phenobarbital • Propylbarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital
Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lorazepam •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 • SL-164
Volatiles/gases: • Acetophenone • Acetylglycinamide chloral hydrate • Centalun • Chloral hydrate • Paraldehyde
Others: Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralose • Clomethiazole • Dichloralphenazone • Etomidate • Gaboxadol • Loreclezole • Metomidate • Org 25435 • Petrichloral • Sulfonmethane • Triclofos • Valerenic acid (Valerian)
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GABAB
agonists |
1,4-Butanediol • Aceburic acid • GABOB • GHB (Sodium oxybate) • GBL • GVL
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H1 inverse
agonists |
Antihistamines: Captodiame • Cyproheptadine • Diphenhydramine • Doxylamine • Hydroxyzine • Methapyrilene • Pheniramine • Promethazine • Propiomazine
Antidepressants: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.)
Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)
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α1-Adrenergic
antagonists |
Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin)
Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)
Others: Niaprazine
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α2-Adrenergic
agonists |
4-NEMD • Clonidine • Detomidine • Dexmedetomidine • Lofexidine • Medetomidine • Romifidine • Tizanidine • Xylazine
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5-HT2A
antagonists |
Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.)
Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)
Others: Eplivanserin • Niaprazine • Pruvanserin • Volinanserin
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Melatonin
agonists |
Agomelatine • LY-156,735 • Melatonin • Ramelteon • Tasimelteon
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Orexin
antagonists |
Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant • TCS-OX2-29
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| Others |
Acecarbromal • Apronal • Bromisoval • Cannabidiol (Cannabis) • Carbromal • Embutramide • Evoxine • Fenadiazole • Gabapentin • Kavalactones (Kava) • Mephenoxalone • Opioids (Oxycodone, Morphine (Opium), etc.) • Passion flower • Scopolamine (Mandrake) • UMB68 • Valnoctamide
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UpToDate Contents
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English Journal
- Anesthetic-induced pain on injection in electroconvulsive therapy: review of the literature and suggestions for prevention.
- Rasmussen KG1, Ritter MJ.
- The journal of ECT.J ECT.2014 Sep;30(3):203-9. doi: 10.1097/YCT.0000000000000088.
- Pain on injection (angialgia) is a common adverse effect of anesthetic medications, especially propofol and methohexital, which are both used for electroconvulsive therapy (ECT). In this review, the authors survey some general literature on angialgia incidence, mechanisms, and prevention efforts in
- PMID 24820946
- Etomidate is Still a Valid Anesthetic for Electroconvulsive Therapy.
- Lebowitz P.
- The journal of ECT.J ECT.2014 Jul 9. [Epub ahead of print]
- Komatsu et al have recently written that the use of etomidate as an anesthetic induction agent for surgery is associated with increased 30-day mortality and cardiovascular morbidity, compared with propofol. Etomidate has long been recognized as suppressing adrenocortical function and, as an infusion
- PMID 25010029
- The safety of propofol sedation for elective nonintubated esophagogastroduodenoscopy in pediatric patients.
- Rajasekaran S1, Hackbarth RM, Davis AT, Kopec JS, Cloney DL, Fitzgerald RK, Hassan NE, Ndika AN, Cornelius K, McCullough A, Sanfilippo D.
- Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies.Pediatr Crit Care Med.2014 Jul;15(6):e261-9. doi: 10.1097/PCC.0000000000000147.
- OBJECTIVES: To evaluate the safety of deep sedation provided by pediatric intensivists for elective nonintubated esophagogastroduodenoscopy.DESIGN: Retrospective observational study.SETTING: The sedation program at the Helen DeVos Children's Hospital.PATIENTS: A 4-year retrospective analysis was don
- PMID 24849145
Japanese Journal
- Sodium Methohexital (Brevital) as an Anesthetic in the Wada Test
- BUCHTEL Henry A.,PASSARO Erasmo A.,SELWA Linda M.,DEVEIKIS John,GOMEZ-HASSAN Diana
- Epilepsia : journal of the International League against Epilepsy 43(9), 1056-1061, 2002-09-01
- NAID 10010878133
- 静脈麻酔剤メトヘキシタール・ナトリウムの麻酔作用ならびに呼吸血圧作用
- 黒木 賀代子,村上 雄次,吉村 泰治,西 正勝
- 九州齒科學會雜誌 : Kyushu-Shika-Gakkai-zasshi 32(3), 298-304, 1978-09-30
- Examinations of the effect of Methohexital-Na were made in rabbits and its anesthetic action was observed by Girndt-Magnus's method. The action on the respiration and blood pressure were recorded by a …
- NAID 110003002794
Related Links
- Brevital [brev´ĭ-tal] trademark for a preparation of methohexital sodium, a barbiturate used as an anesthetic. methohexital (meth-o-hex-i-tal) , Brevital (trade name), Brietal (trade name) Classification Therapeutic: general anesthetics
- What are the possible side effects of methohexital (Brevital Sodium)? Get emergency medical help if you have any of these signs of an allergic reaction: hives; difficulty breathing; swelling of your face, lips, tongue, or throat. Tell your ...
Related Pictures
★リンクテーブル★
[★]
- 英
- methohexital
- 化
- メトヘキシタールナトリウム methohexital sodium
- 商
- Brevital
- 関
- メトヘキシトン。静脈麻酔薬