Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Echothiophate: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 456641807 of page Echothiophate for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL'). |
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{{Short description|Pharmaceutical drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Echothiophate|oldid=456641807}} 456641807] of page [[Echothiophate]] with values updated to verified values.}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
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| IUPAC_name = 2-(Diethoxyphosphorylsulfanyl)ethyl-''N'',''N'',''N''-trimethylazanium iodide |
| IUPAC_name = 2-(Diethoxyphosphorylsulfanyl)ethyl-''N'',''N'',''N''-trimethylazanium iodide |
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| image = Echothiophate iodide.svg |
| image = Echothiophate iodide.svg |
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| width = 170px |
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| image2 = Echothiophate-Molecule-3D-balls.png |
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| width2 = 200px |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = Phospholine |
| tradename = Phospholine |
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| legal_status = |
| legal_status = |
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| routes_of_administration = Topical ([[eye drop]]s) |
| routes_of_administration = Topical ([[eye drop]]s) |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 6736-03-4 |
| CAS_number = 6736-03-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 0F350BVT6S |
| UNII = 0F350BVT6S |
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| KEGG_Ref = {{keggcite| |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02193 |
| KEGG = D02193 |
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| ChEBI_Ref = {{ebicite| |
| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 59849 |
| ChEBI = 59849 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = |
| ChEMBL = 1201341 |
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<!--Chemical data--> |
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| C=9 | H=23 | I=1 | N=1 | O=3 | P=1 | S=1 |
| C=9 | H=23 | I=1 | N=1 | O=3 | P=1 | S=1 |
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| molecular_weight = 383.228 g/mol |
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| smiles = [I-].O=P(OCC)(OCC)SCC[N+](C)(C)C |
| smiles = [I-].O=P(OCC)(OCC)SCC[N+](C)(C)C |
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| InChI = 1/C9H23NO3PS.HI/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5;/h6-9H2,1-5H3;1H/q+1;/p-1 |
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| InChIKey = OVXQHPWHMXOFRD-REWHXWOFAQ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C9H23NO3PS.HI/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5;/h6-9H2,1-5H3;1H/q+1;/p-1 |
| StdInChI = 1S/C9H23NO3PS.HI/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5;/h6-9H2,1-5H3;1H/q+1;/p-1 |
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| StdInChIKey = OVXQHPWHMXOFRD-UHFFFAOYSA-M |
| StdInChIKey = OVXQHPWHMXOFRD-UHFFFAOYSA-M |
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}} |
}} |
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'''Echothiophate''' ('''Phospholine''') is an irreversible [[acetylcholinesterase inhibitor]].<ref name="pmid15277498">{{cite journal |vauthors=Gabelt BT, Hennes EA, Seeman JL, Tian B, Kaufman PL |title=H-7 effect on outflow facility after trabecular obstruction following long-term echothiophate treatment in monkeys |journal=Invest. Ophthalmol. Vis. Sci. |volume=45 |issue=8 |pages=2732–6 |date=August 2004 |pmid=15277498 |doi=10.1167/iovs.04-0083 |url=http://www.iovs.org/cgi/pmidlookup?view=long&pmid=15277498|doi-access= }}</ref> |
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== Uses == |
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It is used as an [[ocular antihypertensive]] in the treatment of open angle [[glaucoma]] and, in some cases, accommodative [[esotropia]]. It is available under several trade names such as Phospholine Iodide ([[Wyeth-Ayerst]]). |
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Echothiophate binds irreversibly to [[cholinesterase]]. Because of the very slow rate at which echothiophate is hydrolyzed by cholinesterase, its effects can last a week or more. [[Adverse drug reaction|Adverse effect]]s include [[muscle spasm]] and other [[systemic effect]]s. |
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== Mechanism of action == |
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It covalently binds by its phosphate group to serine group at the active site of the [[cholinesterase]]. Once bound, the enzyme is permanently inactive and the cell has to make new enzymes. |
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== Shortage == |
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Wyeth Pharmaceuticals stopped manufacturing echothiophate iodide in the US in 2003. After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative Michelle Stephens, the AAO and Wyeth were in talks for about a year about manufacturing it.<ref>{{Cite web |url=http://www.escrs.org/eurotimes/March2003/echo.asp |title=Eurotimes article: "Echothiophate iodide shortage leaves US specialists struggling to find alternative for acute cases" |access-date=2006-08-13 |archive-url=https://web.archive.org/web/20060619040705/http://escrs.org/eurotimes/March2003/echo.asp |archive-date=2006-06-19 |url-status=dead }}</ref> |
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In the meantime, a worldwide shortage of the drug has occurred.{{when|date=April 2023}}{{cn|date=April 2023}} |
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==Chemistry== |
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Echothiophate is made by reacting diethylchlorophosphoric acid with 2-dimethylaminoethylmercaptan, giving ''S''-(2-dimethylaminoethyl)-''O'',''O''-diethylthiophosphate, which is alkylated by [[methyl iodide]], forming echothiophate.<ref>H.M. Fitch, {{US Patent|2911430}} (1959)</ref> |
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:[[File:Echothiophate synthesis.png|600px]] |
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== References == |
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{{Reflist|2}} |
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{{Opthalmologicals}} |
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{{Acetylcholine metabolism and transport modulators}} |
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[[Category:Acetylcholinesterase inhibitors]] |
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[[Category:Iodides]] |
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[[Category:Ophthalmology drugs]] |
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[[Category:Organothiophosphate esters]] |
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[[Category:Phosphorylthiocholines]] |
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