Methohexital


Methohexital
Methohexital
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 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 YesY
ATC code N01AF01 N05CA15
PubChem CID 9034
DrugBank APRD00058
ChemSpider 8683 YesY
UNII E5B8ND5IPE YesY
KEGG D04985 YesY
ChEBI CHEBI:102216 N
ChEMBL CHEMBL7413 YesY
Chemical data
Formula C14H18N2O3 
Mol. mass 262.304
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Methohexital, also called 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

Pharmacology

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 involvedtermination of the drug's biological activity.

Protein binding is approximately 73% for methohexital.[citation needed]

Indications

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

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. Methohexital synthesis.png

W.J. Doran, U.S. Patent 2,872,448 (1959).

References

  1. ^ Katzung, Bertram G., Basic and Clinical Pharmacology, 10th ed., p. 406-407

External links


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Look at other dictionaries:

  • methohexital — /meth oh hek si tal /, n. Pharm. a barbiturate anesthetic, used in its sodium form, C14H17N2NaO3, for induction of general anesthesia or for anesthesia of short duration. [METHO(XY) + HEX + (BARB)IT(URIC ACID) + AL(LYL)] * * * …   Universalium

  • methohexital — noun A barbiturate derived drug used as an anesthetic. Syn: methohexitone …   Wiktionary

  • methohexital — meth·o·hex·i·tal .meth ə hek sə .tȯl, .tal n a barbiturate with a short period of action usu. used in the form of its sodium salt C14H17N2NaO3 as an intravenous general anesthetic * * * meth·o·hex·i·tal (meth″o hekґsĭ təl) [USP]… …   Medical dictionary

  • methohexital — /meth oh hek si tal /, n. Pharm. a barbiturate anesthetic, used in its sodium form, C14H17N2NaO3, for induction of general anesthesia or for anesthesia of short duration. [METHO(XY) + HEX + (BARB)IT(URIC ACID) + AL(LYL)] …   Useful english dictionary

  • methohexital sodium — An ultra short acting barbiturate used intravenously for induction and for general anesthesia of short duration. * * * [USP] the monosodium salt of methohexital, used as a general anesthetic, as an adjunct to general or local anesthesia, and as a …   Medical dictionary

  • Thiamylal — Général Nom IUPAC 5 (pentan 2 yl) 5 (prop 2 èn 1 yl) 2 sulfanylidène 1,3 diazinane 4,6 dione Synonymes …   Wikipédia en Français

  • Ketamine — drugbox IUPAC name = 2 (2 chlorophenyl) 2 methylamino cyclohexan 1 one width = 150 CAS number = 6740 88 1 ATC prefix = N01 ATC suffix = AX03 ATC supplemental = ATC|N01|AX14 PubChem = 3821 DrugBank = APRD00493 C=13 | H=16 | Cl=1 | N=1 | O=1 smiles …   Wikipedia

  • Sodium thiopental — Systematic (IUPAC) name …   Wikipedia

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  • 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 …   Wikipedia


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