Mephenesin

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Mephenesin
Mephenesin.svg
Clinical data
AHFS/Drugs.com International 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 InfoCard 100.000.389 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H14O3
Molar mass 182.219 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 Yes check.svgY
  • Key:JWDYCNIAQWPBHD-UHFFFAOYSA-N Yes check.svgY
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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 [5] Its use has largely been replaced by the related drug methocarbamol, which is better absorbed.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]

Contents

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.

See also

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.