Mephenesin

Identification

Name
Mephenesin
Accession Number
DB13583
Type
Small Molecule
Groups
Approved
Description

Mephenesin is a synthetic cresol glyceryl ether which produces transient muscle relaxation and paralysis via central nervous system depression [1]. It first entered use in the 1950s.

Structure
Thumb
Synonyms
Not Available
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Decontractyl BaumeMephenesin (10 %) + Methyl nicotinate (1 %)OintmentTopicalRobert and Carriere Lab1962-12-311998-07-22Canada
Categories
UNII
7B8PIR2954
CAS number
59-47-2
Weight
Average: 182.219
Monoisotopic: 182.094294311
Chemical Formula
C10H14O3
InChI Key
JWDYCNIAQWPBHD-UHFFFAOYSA-N
InChI
InChI=1S/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3
IUPAC Name
3-(2-methylphenoxy)propane-1,2-diol
SMILES
CC1=CC=CC=C1OCC(O)CO

Pharmacology

Indication

Mephenesin was used for the treatment of muscle spasticity in diseases like Parkinson's or Multiple Sclerosis.

Pharmacodynamics

Mephenesin reduced neuronal excitability leading to decreases action potentials to muscle fibers which ultimately produces a reduction in spasticity [2].

Mechanism of action

The exact mechanism of action of mephenesin is not known. It has been observed to block both inward sodium and inward calcium currents in neurons [3]. It has a physiological effect which opposes that of strychnine.

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
Toxicity

Mephenesin can produce hemolysis leading to hemoglobinuria with intravenous administration of concentrations greater than 10% [1]. As a central nervous system depressant it can also produce paralysis and respiratory depression.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Authors unspecified: NEW and nonofficial remedies; mephenesin. J Am Med Assoc. 1950 Jun 17;143(7):655. [PubMed:15421800]
  2. KAADA BR: Site of action of myanesin in the central nervous system. J Neurophysiol. 1950 Jan;13(1):89-104. doi: 10.1152/jn.1950.13.1.89. [PubMed:15402629]
  3. Klee MR, Faber DS: Mephenesin blocks early inward currents and strychnine-induced multiple discharges of aplysia neurons. Pflugers Arch. 1974 Feb 4;346(2):97-106. [PubMed:4855803]
External Links
ChemSpider
3919
ChEBI
94398
ChEMBL
CHEMBL229128
Wikipedia
Mephenesin
ATC Codes
M03BX06 — Mephenesin
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
OintmentTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)71MSDS
water solubilitySparingly solubleNEW and nonofficial remedies; mephenesin. J Am Med Assoc. 1950;143(7):655.
Predicted Properties
PropertyValueSource
Water Solubility20.8 mg/mLALOGPS
logP0.96ALOGPS
logP1.01ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.82 m3·mol-1ChemAxon
Polarizability19.7 Å3ChemAxon
Number of Rings1ChemAxon
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-MSsplash10-0a4i-5900000000-3ce39ed63d61e07d52b5
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Toluenes / Alkyl aryl ethers / Secondary alcohols / 1,2-diols / Primary alcohols / Hydrocarbon derivatives
Substituents
Phenoxy compound / Phenol ether / Toluene / Alkyl aryl ether / Monocyclic benzene moiety / Secondary alcohol / 1,2-diol / Ether / Organic oxygen compound / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 23, 2017 14:44 / Updated on November 02, 2018 07:42