This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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Identification
- Generic Name
- Mebutamate
- DrugBank Accession Number
- DB06797
- Background
Mebutamate is a sedative and anxiolytic drug with anti-hypertensive (blood pressure lowering) effects comparable to those of other barbiturates but is only around 1/3rd the potency of secobarbital as a sedative. Side effects include dizziness and headaches.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Mebutamate (DB06797)
- Weight
- Average: 232.2768
Monoisotopic: 232.142307138 - Chemical Formula
- C10H20N2O4
- Synonyms
- 2-Methyl-2-sec-butyl-1,3-propanediol dicarbamate
- 2-sec-Butyl-2-methyl-1,3-propanediol dicarbamate
- 2-sec-Butyl-2-methylpropane-1,3-diyl dicarbamate
- 2-sec-Butyl-2-methyltrimethylene dicarbamate
- 2,2-Dicarbamyloxymethyl-3-methylpentane
- Dicamoylmethtane
- Mebutamate
- Mebutamato
- Mebutamatum
- External IDs
- BRN 1788226
- W 583
- W-583
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AGamma-aminobutyric acid receptor subunit gamma-3 modulatorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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 CNS depression can be increased when Mebutamate is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Mebutamate. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Mebutamate. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Mebutamate. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Mebutamate. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Dormate (Medpointe Pharm HLC)
Categories
- ATC Codes
- N05BC04 — Mebutamate
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as carbamate esters. These are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Carbamate esters
- Alternative Parents
- Organic carbonic acids and derivatives / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 5H8F175RER
- CAS number
- 64-55-1
- InChI Key
- LEROTMJVBFSIMP-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H20N2O4/c1-4-7(2)10(3,5-15-8(11)13)6-16-9(12)14/h7H,4-6H2,1-3H3,(H2,11,13)(H2,12,14)
- IUPAC Name
- 2-[(carbamoyloxy)methyl]-2,3-dimethylpentyl carbamate
- SMILES
- CCC(C)C(C)(COC(N)=O)COC(N)=O
References
- Synthesis Reference
U.S. Patent 2,878,280.
- General References
- Tetreault L, Richer P, Bordeleau JM: Hypnotic properties of mebutamate: a comparative study of mebutamate, secobarbital and placebo in psychiatric patients. Can Med Assoc J. 1967 Aug 19;97(8):395-8. [Article]
- External Links
- KEGG Drug
- D01807
- ChemSpider
- 5919
- ChEBI
- 31804
- ChEMBL
- CHEMBL1200922
- Wikipedia
- Mebutamate
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 77-79 U.S. Patent 2,878,280. water solubility 1000 mg/L MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 1.22 mg/mL ALOGPS logP 1.23 ALOGPS logP 1.21 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 15.24 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 104.64 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 57.59 m3·mol-1 Chemaxon Polarizability 24.36 Å3 Chemaxon Number of Rings 0 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 153.43652 predictedDeepCCS 1.0 (2019) [M+H]+ 155.79453 predictedDeepCCS 1.0 (2019) [M+Na]+ 163.94812 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Gamma subunit of the heteropentameric ligand-gated chloride channel gated by gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (By similarity). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (By similarity). When activated by GABA, GABAARs selectively allow the flow of chloride across the cell membrane down their electrochemical gradient (By similarity)
- Specific Function
- GABA-A receptor activity
- Gene Name
- GABRG3
- Uniprot ID
- Q99928
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-3
- Molecular Weight
- 54288.16 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 14, 2010 16:21 / Updated at August 26, 2024 19:24