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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}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 443636316
| Watchedfields = changed
⚫ | IUPAC_name = 4,5-dichlorobenzene-1,3-disulfonamide
⚫ | verifiedrevid = 460783591
⚫ | IUPAC_name = 4,5-Dichlorobenzene-1,3-disulfonamide
| image = Diclofenamide.svg | image = Diclofenamide.svg
| alt = Skeletal formula of diclofenamide

| image2 = Diclofenamide-3D-spacefill.png
| alt2 = Space-filling model of diclofenamide
<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
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| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 6807
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 120-97-8 | CAS_number = 120-97-8
| ATC_prefix = S01 | ATC_prefix = S01
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| ATC_supplemental = | ATC_supplemental =
| PubChem = 3038 | PubChem = 3038
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB07948 | DrugBank = DB01144
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2930 | ChemSpiderID = 2930
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 17 | ChEMBL = 17

<!--Chemical data--> <!--Chemical data-->
| C=6 | H=6 | Cl=2 | N=2 | O=4 | S=2 | C=6 | H=6 | Cl=2 | N=2 | O=4 | S=2
| molecular_weight = 305.16 g/mol
| smiles = Clc1c(cc(cc1Cl)S(=O)(=O)N)S(=O)(=O)N | smiles = Clc1c(cc(cc1Cl)S(=O)(=O)N)S(=O)(=O)N
| 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)
| InChIKey = GJQPMPFPNINLKP-UHFFFAOYAI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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) | 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GJQPMPFPNINLKP-UHFFFAOYSA-N | StdInChIKey = GJQPMPFPNINLKP-UHFFFAOYSA-N
| melting_point = 228.5
}} }}
'''Diclofenamide''' (or '''dichlorphenamide''') is a ] and a ] of the meta-Disulfamoylbenzene class.


'''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.
⚫ ==References==


==Uses==
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/>


==Cost==
* {{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 }}
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>
* {{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}}

⚫ == References ==
{{Reflist}}


{{Antiglaucoma preparations and miotics}} {{Antiglaucoma preparations and miotics}}
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{{antihypertensive-stub}} {{antihypertensive-stub}}

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Latest revision as of 02:48, 9 January 2024

Chemical compound Pharmaceutical compound
Diclofenamide
Skeletal formula of diclofenamide
Space-filling model of diclofenamide
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa601233
ATC code
Pharmacokinetic data
Protein binding55%
Identifiers
IUPAC name
  • 4,5-Dichlorobenzene-1,3-disulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.037 Edit this at Wikidata
Chemical and physical data
FormulaC6H6Cl2N2O4S2
Molar mass305.14 g·mol
3D model (JSmol)
Melting point228.5 °C (443.3 °F)
SMILES
  • Clc1c(cc(cc1Cl)S(=O)(=O)N)S(=O)(=O)N
InChI
  • InChI=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)
  • Key:GJQPMPFPNINLKP-UHFFFAOYSA-N
  (what is this?)  (verify)

Diclofenamide (or dichlorphenamide) is a sulfonamide and a carbonic anhydrase inhibitor 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.

Uses

Diclofenamide was approved in the United States in 1958 as Daranide to treat glaucoma, Subsequently, it was found effective in cases of therapy-resistant epilepsy. In 2015, the medication was approved in the US under the name Keveyis as an orphan drug for the treatment of primary hypokalemic and hyperkalemic periodic paralysis.

Cost

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. 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.

References

  1. ^ "Dichlorphenaide (Keveyis) for Periodic Paralysis". The Medical Letter. April 16, 2016. Retrieved December 19, 2017.
  2. International Drug Names: Diclofenamide
  3. Kanski JJ (August 1968). "Carbonic anhydrase inhibitors and osmotic agents in glaucoma. Carbonic anhydrase inhibitors". The British Journal of Ophthalmology. 52 (8): 642–3. doi:10.1136/bjo.52.8.642. PMC 506660. PMID 5724852.
  4. Rucquoy M, Sorel L (1978). "Diclofenamide in the treatment of therapy-resistant epilepsy". Acta Neurologica Belgica. 78 (3): 174–82. PMID 352085.
  5. ^ Johnson CY (December 18, 2017). "This old drug was free. Now it's $109,500 a year". Washington Post.
Drugs used for glaucoma preparations and miosis (S01E)
Sympathomimetics
Parasympathomimetics
muscarinic
muscarinic/nicotinic
acetylcholinesterase inhibitors
Carbonic anhydrase inhibitors/
(sulfonamides)
Beta blocking agents
Prostaglandin analogues (F2α)
Other agents
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