This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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
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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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Mebutamate is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Mebutamate.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Mebutamate.
AclidiniumMebutamate may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Mebutamate.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Mebutamate.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Mebutamate.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Mebutamate.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Mebutamate.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Mebutamate.
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Food Interactions
Not Available

Products

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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
  1. 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]
KEGG Drug
D01807
ChemSpider
5919
ChEBI
31804
ChEMBL
CHEMBL1200922
Wikipedia
Mebutamate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)77-79U.S. Patent 2,878,280.
water solubility1000 mg/LMERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP1.23ALOGPS
logP1.21ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)15.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.64 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity57.59 m3·mol-1ChemAxon
Polarizability24.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0aba-9200000000-e229dbd3b7da4f2a4429
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at September 14, 2010 16:21 / Updated at February 21, 2021 18:52