NAV

Mephenesin

Identification

Name
Mephenesin
Accession Number
DB13583
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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
3D
Similar Structures
Weight
Average: 182.219
Monoisotopic: 182.094294311
Chemical Formula
C10H14O3
Synonyms
Not Available

Pharmacology

Indication

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

Contraindications & Blackbox Warnings
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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
Adverse Effects
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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
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
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CyclobenzaprineThe risk or severity of CNS depression can be increased when Cyclobenzaprine is combined with Mephenesin.
FluoxetineMephenesin may increase the central nervous system depressant (CNS depressant) activities of Fluoxetine.
HaloperidolThe risk or severity of CNS depression can be increased when Haloperidol is combined with Mephenesin.
LasmiditanThe risk or severity of adverse effects can be increased when Lasmiditan is combined with Mephenesin.
MagnesiumMagnesium can cause a decrease in the absorption of Mephenesin resulting in a reduced serum concentration and potentially a decrease in efficacy.
MetoclopramideThe risk or severity of sedation can be increased when Metoclopramide is combined with Mephenesin.
OliceridineThe risk or severity of hypotension, sedation, death, somnolence, and respiratory depression can be increased when Mephenesin is combined with Oliceridine.
TramadolThe risk or severity of CNS depression can be increased when Mephenesin is combined with Tramadol.
ZiprasidoneThe risk or severity of adverse effects can be increased when Mephenesin is combined with Ziprasidone.
Additional Data Available
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
Not Available

Products

Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Decontractyl BaumeMephenesin (10 %) + Methyl nicotinate (1 %)OintmentTopicalRobert and Carriere Lab1962-12-311998-07-22Canada flag

Categories

ATC Codes
M03BX06 — Mephenesin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-diol / Alcohol / Alkyl aryl ether / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Phenol ether
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
7B8PIR2954
CAS number
59-47-2
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

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]
ChemSpider
3919
BindingDB
50238673
RxNav
6755
ChEBI
94398
ChEMBL
CHEMBL229128
Wikipedia
Mephenesin
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Drug created on June 23, 2017 14:44 / Updated on June 12, 2020 10:53