Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Mephenesin: Difference between pages

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Saving copy of the {{drugbox}} taken from revid 456825480 of page Mephenesin for the Chem/Drugbox validation project (updated: 'CAS_number').
 
I don't think it was used to synthesize meprobamate.
 
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{{Short description|Muscle relaxer & antidote for strychnine poisoning}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Mephenesin|oldid=456825480}} 456825480] of page [[Mephenesin]] with values updated to verified values.}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 408588187
| verifiedrevid = 462248479
| IUPAC_name = 3-(2-methylphenoxy)propane-1,2-diol
| IUPAC_name = 3-(2-methylphenoxy)propane-1,2-diol
| image = Mephenesin.svg
| image = Mephenesin.svg
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| pregnancy_category =
| pregnancy_category =
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| metabolism =
| metabolism =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 59-47-2 -->
| CAS_number = 59-47-2
| ATC_prefix = M03
| ATC_prefix = M03
| ATC_suffix = BX06
| ATC_suffix = BX06
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3919
| ChemSpiderID = 3919
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7B8PIR2954
| UNII = 7B8PIR2954
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 229128
| ChEMBL = 229128
| NIAID_ChemDB = 017830


<!--Chemical data-->
<!--Chemical data-->
| C=10 | H=14 | O=3
| C=10 | H=14 | O=3
| molecular_weight = 182.216 g/mol
| smiles = O(c1ccccc1C)CC(O)CO
| smiles = O(c1ccccc1C)CC(O)CO
| InChI = 1/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3
| InChIKey = JWDYCNIAQWPBHD-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3
| StdInChI = 1S/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3
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| StdInChIKey = JWDYCNIAQWPBHD-UHFFFAOYSA-N
| StdInChIKey = JWDYCNIAQWPBHD-UHFFFAOYSA-N
}}
}}

'''Mephenesin''' ([[International nonproprietary name|INN]]), also called '''myanesin''',<ref>{{cite web |title=Mephenesin Definition & Meaning |url=https://www.merriam-webster.com/medical/mephenesin |website=Merriam-Webster Medical}}</ref><ref name="pmid19108125">{{cite journal | vauthors = Berger FM | title = The mode of action of myanesin | journal = British Journal of Pharmacology and Chemotherapy | volume = 2 | issue = 4 | pages = 241–50 | date = December 1947 | pmid = 19108125 | pmc = 1509790 | doi = 10.1111/j.1476-5381.1947.tb00341.x }}</ref> 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.<ref>{{cite web|title=Mephenesin|url=https://www.mims.com/USA/drug/info/mephenesin/|publisher=MIMS}}</ref> Mephenesin was the inspiration for the synthesis of a derivative of [[1,3-propanediol]], [[meprobamate]], by Bernard Ludwig and [[Frank Berger]],<ref>{{cite journal | vauthors = Ban TA | title = The role of serendipity in drug discovery | journal = Dialogues in Clinical Neuroscience | volume = 8 | issue = 3 | pages = 335–44 | date = 2006 | pmid = 17117615 | pmc = 3181823 | doi = 10.31887/DCNS.2006.8.3/tban }}</ref> 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.<ref>{{cite web|title=Mephenesin|url=https://www.drugs.com/international/mephenesin.html|publisher=Drugs.com}}</ref> Its use has largely been replaced by the related drug [[methocarbamol]], which is better absorbed.<ref>{{cite journal|last=Huf|first=Ernst|title=Comparative Plasma Levels of Mephenesin, Mephenesin Carbamate and Methocarbamol|journal=Proceedings of the Society for Experimental Biology and Medicine|year=1959|volume=102|issue=2|pages=276–7|url=http://ebm.sagepub.com/content/102/2/276.abstract|publisher=Experimental Biology & Medicine|doi=10.3181/00379727-102-25218|pmid=14403806|s2cid=37483102|access-date=8 January 2014|display-authors=etal}}</ref>

Mephenesin may be an [[NMDA receptor antagonist]].<ref name="pmid23825891">{{cite journal | vauthors = Keshavarz M, Showraki A, Emamghoreishi M | title = Anticonvulsant Effect of Guaifenesin against Pentylenetetrazol-Induced Seizure in Mice | journal = Iran J Med Sci | volume = 38 | issue = 2 | pages = 116–21 | year = 2013 | pmid = 23825891 | pmc = 3700057 }}</ref> 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==
* [[Chlorphenesin]]
* [[Guaifenesin]]
* [[Mephenoxalone]]
* [[Methocarbamol]]
* [[Prenderol]]

==External links==
* {{cite journal |vauthors=Bachmeyer C, Blum L, Fléchet M, Duriez P, Cabane J, Imbert J | title = [Severe contact dermatitis caused by mephenesin] | journal = Ann Dermatol Venereol | volume = 123 | issue = 3 | pages = 185–7 | year = 1996 | pmid = 8761781}}
* {{cite journal |vauthors=Ono H, Nakamura T, Ito H, Oka J, Fukuda H | title = Rigidity in rats due to radio frequency decerebration and effects of chlorpromazine and mephenesin | journal = Gen Pharmacol | volume = 18 | issue = 1 | pages = 57–9 | year = 1987 | pmid = 3557053 | doi=10.1016/0306-3623(87)90170-4}}

==References==
{{Reflist}}

{{Muscle relaxants}}

[[Category:Diols]]
[[Category:Drugs with unknown mechanisms of action]]
[[Category:Muscle relaxants]]
[[Category:Phenol ethers]]


{{musculoskeletal-drug-stub}}
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