| Revision as of 14:52, 15 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit |
Latest revision as of 02:48, 9 January 2024 edit undoMichael7604 (talk | contribs)Extended confirmed users8,895 edits change category from Chlorobenzenes to Chlorobenzene derivatives |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 443636316 |
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| Watchedfields = changed |
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| IUPAC_name = 4,5-dichlorobenzene-1,3-disulfonamide |
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| verifiedrevid = 460783591 |
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| IUPAC_name = 4,5-Dichlorobenzene-1,3-disulfonamide |
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| image = Diclofenamide.svg |
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| image = Diclofenamide.svg |
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| alt = Skeletal formula of diclofenamide |
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| image2 = Diclofenamide-3D-spacefill.png |
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| alt2 = Space-filling model of diclofenamide |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 6807 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 120-97-8 |
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| CAS_number = 120-97-8 |
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| ATC_prefix = S01 |
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| ATC_prefix = S01 |
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| ATC_supplemental = |
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| ATC_supplemental = |
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| PubChem = 3038 |
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| PubChem = 3038 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB07948 |
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| DrugBank = DB01144 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2930 |
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| ChemSpiderID = 2930 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 17 |
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| ChEMBL = 17 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=6 | H=6 | Cl=2 | N=2 | O=4 | S=2 |
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| C=6 | H=6 | Cl=2 | N=2 | O=4 | S=2 |
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| molecular_weight = 305.16 g/mol |
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| smiles = Clc1c(cc(cc1Cl)S(=O)(=O)N)S(=O)(=O)N |
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| smiles = Clc1c(cc(cc1Cl)S(=O)(=O)N)S(=O)(=O)N |
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| InChI = 1/C6H6Cl2N2O4S2/c7-4-1-3(15(9,11)12)2-5(6(4)8)16(10,13)14/h1-2H,(H2,9,11,12)(H2,10,13,14) |
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| InChIKey = GJQPMPFPNINLKP-UHFFFAOYAI |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H6Cl2N2O4S2/c7-4-1-3(15(9,11)12)2-5(6(4)8)16(10,13)14/h1-2H,(H2,9,11,12)(H2,10,13,14) |
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| StdInChI = 1S/C6H6Cl2N2O4S2/c7-4-1-3(15(9,11)12)2-5(6(4)8)16(10,13)14/h1-2H,(H2,9,11,12)(H2,10,13,14) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GJQPMPFPNINLKP-UHFFFAOYSA-N |
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| StdInChIKey = GJQPMPFPNINLKP-UHFFFAOYSA-N |
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| melting_point = 228.5 |
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}} |
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}} |
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'''Diclofenamide''' (or '''dichlorphenamide''') is a ] and a ] of the meta-Disulfamoylbenzene class. |
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'''Diclofenamide''' (or '''dichlorphenamide''') is a ] and a ] of the ''meta''-disulfamoylbenzene class. Dichlorphenamide as a carbonic anhydrase inhibitor is used for the treatment of acute angle closure glaucoma. While Dichlorphenamide does contain two sulfate groups within the structure, it falls under the class of a first generation carbonic anhydrase Inhibitor. |
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==References== |
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==Uses== |
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Diclofenamide was approved in the United States in 1958 as ''Daranide'' to treat ],<ref name=ML>{{cite news |url=https://secure.medicalletter.org/article-share?a=1492d&p=tml&title=Dichlorphenamide%20(Keveyis)%20for%20Periodic%20Paralysis&cannotaccesstitle=1 |title=Dichlorphenaide (Keveyis) for Periodic Paralysis |publisher=The Medical Letter |date=April 16, 2016 |access-date=December 19, 2017}}</ref><ref>{{drugs.com|international|diclofenamide.html}}: Diclofenamide</ref><ref>{{cite journal | vauthors = Kanski JJ | title = Carbonic anhydrase inhibitors and osmotic agents in glaucoma. Carbonic anhydrase inhibitors | journal = The British Journal of Ophthalmology | volume = 52 | issue = 8 | pages = 642–3 | date = August 1968 | pmid = 5724852 | pmc = 506660 | doi = 10.1136/bjo.52.8.642 }}</ref> Subsequently, it was found effective in cases of therapy-resistant ].<ref>{{cite journal | vauthors = Rucquoy M, Sorel L | title = Diclofenamide in the treatment of therapy-resistant epilepsy | journal = Acta Neurologica Belgica | volume = 78 | issue = 3 | pages = 174–82 | year = 1978 | pmid = 352085 }}</ref> In 2015, the medication was approved in the US under the name ''Keveyis'' as an ] for the treatment of primary hypokalemic and hyperkalemic ].<ref name=ML/><ref name=WP/> |
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==Cost== |
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* {{cite journal | author = Tawil R, McDermott M, Brown R, Shapiro B, Ptacek L, McManis P, Dalakas M, Spector S, Mendell J, Hahn A, Griggs R | title = Randomized trials of dichlorphenamide in the periodic paralyses. Working Group on Periodic Paralysis. | journal = Ann Neurol | volume = 47 | issue = 1 | pages = 46–53 | year = 2000 | pmid = 10632100 | doi = 10.1002/1531-8249(200001)47:1<46::AID-ANA9>3.0.CO;2-H }} |
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In 2001, diclofenamide had a U.S. list price of $50 for a bottle of 100 pills, and was approved for glaucoma. Merck discontinued diclofenamide when better glaucoma drugs were developed. In 2010, Sun Pharmaceutical Industries bought the rights.{{Citation needed|date=April 2023}} In 2015, the F.D.A. approved it as an orphan drug, with 7-year exclusive marketing rights, for periodic paralysis, which the company estimates affects 5,000 people in the U.S. In 2016, Strongbridge Biopharma acquired Sun, which raised the price to $15,001 for 100 pills. The cost of treatment would range from $109,500 to $219,000 a year. Sun gives the drug free to patients who don't have insurance.<ref name=WP>{{cite news | url = https://www.washingtonpost.com/news/wonk/wp/2017/12/18/this-old-drug-was-free-now-its-109500-a-year/ | title = This old drug was free. Now it's $109,500 a year. | first = Carolyn Y. | last = Johnson | name-list-style = vanc | newspaper = Washington Post | date = December 18, 2017 }}</ref> |
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* {{cite journal | author = Okada S, Izumi W, Murai M, Komatsu H, Ishimitsu S | title = | journal = Eisei Shikenjo Hokoku | volume = 109 | issue = 109| pages = 148–50 | year = 1991 | pmid = 1364383}} |
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== References == |
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{{Reflist}} |
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{{Antiglaucoma preparations and miotics}} |
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{{Antiglaucoma preparations and miotics}} |
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{{antihypertensive-stub}} |
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{{antihypertensive-stub}} |
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