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Mephenesin

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Mephenesin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 3-(2-methylphenoxy)propane-1,2-diol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.389 Edit this at Wikidata
Chemical and physical data
FormulaC10H14O3
Molar mass182.219 g·mol−1
3D model (JSmol)
  • O(c1ccccc1C)CC(O)CO
  • 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 checkY
  • Key:JWDYCNIAQWPBHD-UHFFFAOYSA-N checkY
 ☒NcheckY (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is no longer available in North America but is used in Italy and a few other countries.[5] Its use has largely been replaced by the related drug methocarbamol, which is better absorbed.[6]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 is, however, still available in Italy.

See also

  • Bachmeyer C, Blum L, Fléchet M, Duriez P, Cabane J, Imbert J (1996). "[Severe contact dermatitis caused by mephenesin]". Ann Dermatol Venereol. 123 (3): 185–7. PMID 8761781.
  • Ono H, Nakamura T, Ito H, Oka J, Fukuda H (1987). "Rigidity in rats due to radio frequency decerebration and effects of chlorpromazine and mephenesin". Gen Pharmacol. 18 (1): 57–9. doi:10.1016/0306-3623(87)90170-4. PMID 3557053.

References

  1. ^ "Mephenesin Definition & Meaning". Merriam-Webster Medical.
  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.
  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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