Mephenesin

Mephenesin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M03BX06 (WHO) ;
Identifiers
	IUPAC name 3-(2-methylphenoxy)propane-1,2-diol;
CAS Number	59-47-2 ;
PubChem CID	4059;
ChemSpider	3919 ;
UNII	7B8PIR2954;
KEGG	D02595 ;
ChEMBL	ChEMBL229128 ;
NIAID ChemDB	017830;
CompTox Dashboard (EPA)	DTXSID4023254 ;
ECHA InfoCard	100.000.389
Chemical and physical data
Formula	C10H14O3
Molar mass	182.219 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1ccccc1C)CC(O)CO;
	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 ; Key:JWDYCNIAQWPBHD-UHFFFAOYSA-N ;
	(what is this?) (verify)

Mephenesin (INN), also called myanesin,^[1]^[2] is a centrally acting muscle relaxant. It can be used as an antidote for strychnine poisoning. Mephenesin however presents with the major drawbacks of having a short duration of action and a much greater effect on the spinal cord than the brain, resulting in pronounced respiratory depression at clinical doses and therefore a very low therapeutic index. It is especially dangerous and potentially fatal in combination with alcohol and other depressants.^[3] Mephenesin was the inspiration for the synthesis of a derivative of 1,3-propanediol, meprobamate, by Bernard Ludwig and Frank Berger,^[4] the first tranquilizer to see widespread clinical use. Mephenesin is no longer available in North America but is used in Italy and a few other countries.^[5] Its use has largely been replaced by the related drug methocarbamol, which is better absorbed.^[6]

Mephenesin may be an NMDA receptor antagonist.^[7] Mephenesin was previously used in France as an OTC muscle relaxant called Décontractyl but was taken out of production by Sanofi Aventis and due to a French Health Ministry decree in July 2019.

^ "Mephenesin Definition & Meaning". Merriam-Webster Medical.
^ Berger FM (December 1947). "The mode of action of myanesin". British Journal of Pharmacology and Chemotherapy. 2 (4): 241–50. doi:10.1111/j.1476-5381.1947.tb00341.x. PMC 1509790. PMID 19108125.
^ "Mephenesin". MIMS.
^ Ban TA (2006). "The role of serendipity in drug discovery". Dialogues in Clinical Neuroscience. 8 (3): 335–44. doi:10.31887/DCNS.2006.8.3/tban. PMC 3181823. PMID 17117615.
^ "Mephenesin". Drugs.com.
^ Huf, Ernst; et al. (1959). "Comparative Plasma Levels of Mephenesin, Mephenesin Carbamate and Methocarbamol". Proceedings of the Society for Experimental Biology and Medicine. 102 (2). Experimental Biology & Medicine: 276–7. doi:10.3181/00379727-102-25218. PMID 14403806. S2CID 37483102. Retrieved 8 January 2014.
^ Keshavarz M, Showraki A, Emamghoreishi M (2013). "Anticonvulsant Effect of Guaifenesin against Pentylenetetrazol-Induced Seizure in Mice". Iran J Med Sci. 38 (2): 116–21. PMC 3700057. PMID 23825891.

[1] "Mephenesin Definition & Meaning". Merriam-Webster Medical.

[pmid19108125-2] Berger FM (December 1947). "The mode of action of myanesin". British Journal of Pharmacology and Chemotherapy. 2 (4): 241–50. doi:10.1111/j.1476-5381.1947.tb00341.x. PMC 1509790. PMID 19108125.

[3] "Mephenesin". MIMS.

[4] Ban TA (2006). "The role of serendipity in drug discovery". Dialogues in Clinical Neuroscience. 8 (3): 335–44. doi:10.31887/DCNS.2006.8.3/tban. PMC 3181823. PMID 17117615.

[5] "Mephenesin". Drugs.com.

[6] Huf, Ernst; et al. (1959). "Comparative Plasma Levels of Mephenesin, Mephenesin Carbamate and Methocarbamol". Proceedings of the Society for Experimental Biology and Medicine. 102 (2). Experimental Biology & Medicine: 276–7. doi:10.3181/00379727-102-25218. PMID 14403806. S2CID 37483102. Retrieved 8 January 2014.

[pmid23825891-7] Keshavarz M, Showraki A, Emamghoreishi M (2013). "Anticonvulsant Effect of Guaifenesin against Pentylenetetrazol-Induced Seizure in Mice". Iran J Med Sci. 38 (2): 116–21. PMC 3700057. PMID 23825891.

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