MEPHENESIN

US Previously Marketed

First approved in 1948

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H14O3
Molecular Weight	182.2164
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(OCC(O)CO)C=CC=C1

InChI

InChIKey=JWDYCNIAQWPBHD-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.pharma-medicaments.com/media/3512060__017142000_1759_24052013.pdf
Curator's Comment: description was created based on several sources, including: http://www.medindia.net/doctors/drug_information/mephenesin.htm | https://www.ncbi.nlm.nih.gov/pubmed/18886031

Mephenesin is a centrally acting muscle relaxant. This medication is prescribed for muscle spasm. It can be used as an antidote for strychnine poisoning. Most common side effects are: lassitude, drowsiness, weakness, loss of appetite, nausea and vomiting, hypersensitivity reactions. Its clinical usefulness is considered to be limited by its brief duration of action.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 46 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7912632 \| https://www.ncbi.nlm.nih.gov/pubmed/1378953	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Painful muscular contractions 1 Sources: https://www.pharma-medicaments.com/media/3512060__017142000_1759_24052013.pdf	Palliative		Approved 8429	Decontractyl Approved Use It is indicated for the supportive treatment of painful muscle contractions.

Doses

Dose	Population	Adverse events
500 mg single, oral Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24814457	healthy, 25 years n = 1 Health Status: healthy Age Group: 25 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/24814457	Disc. AE: Anaphylactic shock... AEs leading to discontinuation/dose reduction: Anaphylactic shock Sources: https://pubmed.ncbi.nlm.nih.gov/24814457
7.5 g single, oral Overdose Dose: 7.5 g Route: oral Route: single Dose: 7.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/17209942	healthy, 48 years n = 1 Health Status: healthy Age Group: 48 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17209942	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/17209942

AEs

AE	Significance	Dose	Population
Anaphylactic shock	Disc. AE	500 mg single, oral Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24814457	healthy, 25 years n = 1 Health Status: healthy Age Group: 25 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/24814457
Adverse event	grade 5	7.5 g single, oral Overdose Dose: 7.5 g Route: oral Route: single Dose: 7.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/17209942	healthy, 48 years n = 1 Health Status: healthy Age Group: 48 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17209942

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY562102	https://www.001chemical.com/chem/59-47-2
AA Blocks	AA00E9FU	http://www.aablocks.com/goods/Goods/detail?id=AA00E9FU
AK Scientific, Inc. (AKSCI)	W0052	http://www.aksci.com/item_detail.php?cat=W0052
Aaron Chemicals	AR00EA7M	http://www.aaronchem.com/59-47-2
AbMole Bioscience	M5769	http://www.abmole.com/products/mephenesin.html
Acadechem	ACDS-033174	http://www.acadechemical.com/product/107873
Ark Pharm	AK546793	http://www.arkpharminc.com/products/59-47-2.html
BLD Pharm	BD137421	http://www.bldpharm.com/products/59-47-2.html
CSNpharm	CSN11379	https://www.csnpharm.com/products/mephenesin.html
Chem Scene	CS-5340	http://www.chemscene.com/59-47-2.html
Chemspace	CSSB00011215453	https://chem-space.com/CSSB00011215453
Clearsynth	CS-DE-01388	https://www.clearsynth.com/en/CSDE01388.html
DC Chemicals	DC34654	http://www.dcchemicals.com//product_show-Mephenesin.html
Finetech	FT-0628209	http://www.finetechnology-ind.com/prod/detail/pub/59-47-2.html
LGC Standards	LGCFOR0810.00	https://www.lgcstandards.com/US/en/p/LGCFOR0810.00
LGC Standards	MM0810.00	https://www.lgcstandards.com/US/en/p/MM0810.00
Lab Network	LN00196153	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00196153
MedChem Express	HY-B1283	https://www.medchemexpress.com/Mephenesin.html
Molcore	MC562102	https://www.molcore.com/product/59-47-2
MuseChem	I004227	https://www.musechem.com/product/I004227.html
Sigma-Aldrich	286567_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/286567?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	S423300_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s423300
Sinfoo Biotech	S017517	http://www.sinfoobiotech.com/product/1020915
Smolecule	S534976	http://www.smolecule.com/products/s534976
THE BioTek	bt-274757	https://www.thebiotek.com/product/inhibitors/bt-274757
abcr GmbH	AB134044	http://www.abcr.com/shop/en/AB134044
eNovation Chemicals	D669825	https://www.enovationchem.com/ProductDetails.asp?ProductID=D669825
iChemical	EBD70999	http://www.ichemical.com/products/59-47-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1125347766	https://mcule.com/MCULE-1125347766/

PubMed

Title	Date	PubMed
DDT-induced tremor in rats: effects of pharmacological agents.	1985	3929313
Analysis of neutral drugs in human plasma by fluoride attachment in liquid chromatography/negative ion electrospray tandem mass spectrometry.	2004	15329856
Determination of guaifenesin in human serum by capillary gas chromatography and electron capture detection.	2004 Jun 29	15193724
Descending respiratory polysynaptic inputs to cervical and thoracic motoneurons diminish during early postnatal maturation in rat spinal cord.	2005 Feb	15733100
Acupuncture therapy rapidly terminates intractable hiccups complicating acute myocardial infarction.	2005 Mar	15813167
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs.	2005 Sep-Oct	16125625
The role of serendipity in drug discovery.	2006	17117615
Spinal ventral root after-discharges as a pain index: involvement of NK-1 and NMDA receptors.	2006 Apr 12	16507302
Activity of common anticonvulsant drugs on spinal seizure-induced by sudden cooling.	2006 Sep 30	16626844
The synthesis of amphipathic prodrugs of 1,2-diol drugs with saccharide conjugates by high regioselective enzymatic protocol.	2007 Feb 15	17178228
Fatal mephenesin intoxication.	2007 Jan	17209942
Comparison of atmospheric pressure photoionization and atmospheric pressure chemical ionization for normal-phase LC/MS chiral analysis of pharmaceuticals.	2007 Mar 15	17288463
Strategy for identification of leachables in packaged pharmaceutical liquid formulations.	2008 Feb 13	18180126
Three different types of chirality-driven crystallization within the series of uniformly substituted phenyl glycerol ethers.	2008 Nov	18767134
Stability indicating HPLC method for simultaneous determination of mephenesin and diclofenac diethylamine.	2009 Jan	20177453
[Acute generalized exanthematous pustulosis induced by topical application of Algipan].	2009 Oct	19801255
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Bicuculline-sensitive primary afferent depolarization remains after greatly restricting synaptic transmission in the mammalian spinal cord.	2010 Apr 14	20392950
Segmental patterns of vestibular-mediated synaptic inputs to axial and limb motoneurons in the neonatal mouse assessed by optical recording.	2010 Dec 15	20962007
Age estimation in 25-45 yrs. old females by physical and radiological methods.	2010 Jul	21731347
Permeability evaluation through chitosan membranes using taguchi design.	2010 Oct-Dec	21179329

Patents

Sample Use Guides

In Vivo Use Guide

Oral: 1 to 2 tablets per dose (500 - 1000 mg), 3 times daily Topical: 2 to 3 times a day with area messages of about ten minutes (duration - 5 days).

Route of Administration: Other

In Vitro Use Guide

Mephenesin is oxidatively metabolized in vitro 'by rat and mouse liver slices to 3- (o-tolyloxy)lactic acid. The uMoles of mephenesin metabolized per gram of fresh tissue was apparently a linear relationship with time up to 60 minutes. The maximum percent of substrate oxidized occurred between 1 500- 2000 ug.

Name

Type

Language

MEPHENESIN

Official Name

English

MEPHENESIN [MI]

Common Name

English

Mephenesin [WHO-DD]

Common Name

English

MEPHENESIN [MART.]

Common Name

English

TOLSEROL

Code

English

mephenesin [INN]

Common Name

English

NSC-25234

Code

English

3-(O-METHYLPHENOXY)-1,2-PROPANEDIOL

Common Name

English

MEPHENESINE

Common Name

English

Classification Tree Code System Code

WHO-ATC

M03BX06