Mephenesin
Identification
- Summary
Mephenesin is a cresol glyceryl ether used to treat muscle spasticity in Parkinson's and Multiple Sclerosis.
- Generic Name
- Mephenesin
- DrugBank Accession Number
- DB13583
- Background
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
Structure for Mephenesin (DB13583)
- Weight
- Average: 182.219
Monoisotopic: 182.094294311 - Chemical Formula
- C10H14O3
- Synonyms
- Mephenesin
Pharmacology
- Indication
Mephenesin was used for the treatment of muscle spasticity in diseases like Parkinson's or Multiple Sclerosis.
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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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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.
- 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 softwareCyclobenzaprine The risk or severity of CNS depression can be increased when Cyclobenzaprine is combined with Mephenesin. Fluoxetine Mephenesin may increase the central nervous system depressant (CNS depressant) activities of Fluoxetine. Haloperidol The risk or severity of CNS depression can be increased when Haloperidol is combined with Mephenesin. Lasmiditan The risk or severity of adverse effects can be increased when Lasmiditan is combined with Mephenesin. Metoclopramide The risk or severity of sedation can be increased when Metoclopramide is combined with Mephenesin. Oliceridine The risk or severity of hypotension, sedation, death, somnolence, and respiratory depression can be increased when Mephenesin is combined with Oliceridine. Tramadol The risk or severity of CNS depression can be increased when Mephenesin is combined with Tramadol. Ziprasidone The risk or severity of adverse effects can be increased when Mephenesin is combined with Ziprasidone. 
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- Not Available
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Decontractyl Baume Mephenesin (10 %) + Methyl nicotinate (1 %) Ointment Topical Robert and Carriere Lab 1962-12-31 1998-07-22 Canada 
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
- Affected organisms
- 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
- Authors unspecified: NEW and nonofficial remedies; mephenesin. J Am Med Assoc. 1950 Jun 17;143(7):655. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- ChemSpider
- 3919
- BindingDB
- 50238673
- 6755
- ChEBI
- 94398
- ChEMBL
- CHEMBL229128
- Wikipedia
- Mephenesin
- MSDS
- Download (47 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Ointment Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 71 MSDS water solubility Sparingly soluble NEW and nonofficial remedies; mephenesin. J Am Med Assoc. 1950;143(7):655. - Predicted Properties
Property Value Source Water Solubility 20.8 mg/mL ALOGPS logP 0.96 ALOGPS logP 1.01 ChemAxon logS -0.94 ALOGPS pKa (Strongest Acidic) 13.62 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 49.69 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 49.82 m3·mol-1 ChemAxon Polarizability 19.7 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - EI-B GC-MS splash10-0a4i-5900000000-3ce39ed63d61e07d52b5 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
Drug created on June 23, 2017 20:44 / Updated on February 21, 2021 18:54