Identification
- Summary
Methohexital is an anesthetic used to induce deep sedation.
- Brand Names
- Brevital
- Generic Name
- Methohexital
- DrugBank Accession Number
- DB00474
- Background
An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Methohexital (DB00474)
- Weight
- Average: 262.3043
Monoisotopic: 262.131742452 - Chemical Formula
- C14H18N2O3
- Synonyms
- (±)-5-allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acid
- 5-allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
- 5-Allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trione
- 5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acid
- Methohexital
- Methohexitalum
- Methohexitone
- Metohexital
- α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric acid
Pharmacology
- Indication
Methohexital is indicated for use as an intravenous anaesthetic. It has also been commonly used to induce deep sedation.
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- Contraindications & Blackbox Warnings
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Methohexital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
- Mechanism of action
Methohexital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Target Actions Organism AGamma-aminobutyric acid receptor subunit alpha-1 antagonistHumans - Absorption
The absolute bioavailability following rectal administration of methohexital is 17%.
- Volume of distribution
Not Available
- Protein binding
73%
- Metabolism
Metabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity.
- Route of elimination
Excretion occurs via the kidneys through glomerular filtration.
- Half-life
5.6 ± 2.7 minutes
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The onset of toxicity following an overdose of intravenously administered methohexital will be within seconds of the infusion. If methohexital is administered rectally or is ingested, the onset of toxicity may be delayed. The manifestations of an ultrashort-acting barbiturate in overdose include central nervous system depression, respiratory depression, hypotension, loss of peripheral vascular resistance, and muscular hyperactivity ranging from twitching to convulsive-like movements. Other findings may include convulsions and allergic reactions. Following massive exposure to any barbiturate, pulmonary edema, circulatory collapse with loss of peripheral vascular tone, and cardiac arrest may occur.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Methohexital is combined with 1,2-Benzodiazepine. Abaloparatide Methohexital may increase the hypotensive activities of Abaloparatide. Acebutolol Methohexital may increase the hypotensive activities of Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Methohexital. Acetaminophen The metabolism of Acetaminophen can be increased when combined with Methohexital. Acetazolamide The risk or severity of adverse effects can be increased when Methohexital is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Methohexital is combined with Acetophenazine. Agomelatine The risk or severity of adverse effects can be increased when Methohexital is combined with Agomelatine. Aldesleukin Methohexital may increase the hypotensive activities of Aldesleukin. Alfentanil The risk or severity of adverse effects can be increased when Methohexital is combined with Alfentanil. 
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- Avoid alcohol. Alcohol intake may cause additive CNS depressant effects.
Products
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Ingredient UNII CAS InChI Key Methohexital sodium 60200PNZ7Q 309-36-4 KDXZREBVGAGZHS-UHFFFAOYSA-M - International/Other Brands
- Brevital / Brietal
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Brevital Sodium Injection, powder, lyophilized, for solution 200 mg/1 Intramuscular; Intravenous; Rectal JHP Pharmaceuticals LLC 2013-03-20 2013-03-14 US 
Brevital Sodium Injection 2.5 g/1 Intramuscular; Rectal Monarch Pharmaceuticals, Inc. 2006-10-10 2006-11-22 US Brevital Sodium Injection, powder, lyophilized, for solution 2.5 g/1 Intramuscular; Intravenous; Rectal Par Pharmaceutical, Inc. 2007-11-01 2021-01-31 US Brevital Sodium Injection, powder, lyophilized, for solution 500 mg/1 Intramuscular; Intravenous; Rectal A S Medication Solutions 2007-11-01 2013-06-07 US Brevital Sodium Injection 500 mg/1 Intramuscular; Rectal Monarch Pharmaceuticals, Inc. 2006-10-10 2006-11-22 US Brevital Sodium Injection, powder, lyophilized, for solution 500 mg/1 Intramuscular; Intravenous; Rectal Par Pharmaceutical, Inc. 2007-11-01 Not applicable US Brevital Sodium Injection, powder, lyophilized, for solution 500 mg/5mL Intramuscular; Intravenous; Rectal Physicians Total Care, Inc. 1960-06-27 2003-06-30 US
Categories
- ATC Codes
- N05CB01 — Combinations of barbiturates
- N05CB — Barbiturates, combinations
- N05C — HYPNOTICS AND SEDATIVES
- N05 — PSYCHOLEPTICS
- N — NERVOUS SYSTEM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Barbituric acid derivatives
- Alternative Parents
- N-acyl ureas / Diazinanes / Dicarboximides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 1,3-diazinane / Aliphatic heteromonocyclic compound / Azacycle / Barbiturate / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide / Hydrocarbon derivative / N-acyl urea
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- barbiturates, acetylenic compound (CHEBI:102216)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- E5B8ND5IPE
- CAS number
- 151-83-7
- InChI Key
- NZXKDOXHBHYTKP-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
- SMILES
- CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014617
- KEGG Drug
- D04985
- KEGG Compound
- C07844
- PubChem Compound
- 9034
- PubChem Substance
- 46507954
- ChemSpider
- 8683
- 6847
- ChEBI
- 102216
- ChEMBL
- CHEMBL7413
- Therapeutic Targets Database
- DAP000677
- PharmGKB
- PA164784030
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Methohexital
- FDA label
- Download (184 KB)
- MSDS
- Download (46.5 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Atrial Fibrillation / Atrial Flutter 1 4 Completed Treatment Depression 1 4 Completed Treatment Depression, Bipolar / Unipolar Depression 1 4 Recruiting Treatment Depression / Electroconvulsive Therapy 1 0 Completed Diagnostic Cortical Spreading Depression / Direct Current Electroencephalogram / Electroconvulsive Therapy / Ketamine 1 Not Available Completed Treatment Anesthesia therapy / Hypotension 1 Not Available Completed Treatment Depression 1 Not Available Completed Treatment Major Depressive Disorder (MDD) 1 Not Available Completed Treatment Orientation / Post-anesthesia Recovery 1 Not Available Terminated Treatment Depression, Bipolar / Major Depressive Disorder (MDD) 1
Pharmacoeconomics
- Manufacturers
- Jhp pharmaceuticals llc
- Packagers
- JHP Pharmaceuticals LLC
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Injection Intramuscular; Rectal 2.5 g/1 Injection Intramuscular; Rectal 500 mg/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous; Rectal 2.5 g/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous; Rectal 200 mg/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous; Rectal 500 mg/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous; Rectal 500 mg/5mL Injection, powder, for solution Parenteral Powder, for solution Intravenous 500 mg / amp - Prices
Unit description Cost Unit Brevital sodium 2.5 gm vial 221.2USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 1.8 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0524 mg/mL ALOGPS logP 2.43 ALOGPS logP 2.29 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 7.73 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 66.48 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 71.51 m3·mol-1 Chemaxon Polarizability 27.4 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9143 Blood Brain Barrier + 0.982 Caco-2 permeable + 0.5 P-glycoprotein substrate Non-substrate 0.6307 P-glycoprotein inhibitor I Inhibitor 0.5661 P-glycoprotein inhibitor II Non-inhibitor 0.9294 Renal organic cation transporter Non-inhibitor 0.9297 CYP450 2C9 substrate Non-substrate 0.823 CYP450 2D6 substrate Non-substrate 0.8823 CYP450 3A4 substrate Non-substrate 0.6454 CYP450 1A2 substrate Non-inhibitor 0.8001 CYP450 2C9 inhibitor Non-inhibitor 0.8179 CYP450 2D6 inhibitor Non-inhibitor 0.9099 CYP450 2C19 inhibitor Non-inhibitor 0.7836 CYP450 3A4 inhibitor Non-inhibitor 0.8501 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.954 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.8264 Biodegradation Not ready biodegradable 0.9737 Rat acute toxicity 2.9098 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.978 hERG inhibition (predictor II) Non-inhibitor 0.9697
Spectra
- Mass Spec (NIST)
- Download (12.5 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0fbc-9520000000-5141cdceea7f6d5013b0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Koltchine VV, Ye Q, Finn SE, Harrison NL: Chimeric GABAA/glycine receptors: expression and barbiturate pharmacology. Neuropharmacology. 1996;35(9-10):1445-56. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:16