diclofenamide
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460783591
| IUPAC_name = 4,5-Dichlorobenzene-1,3-disulfonamide
| image = Diclofenamide.svg
| alt = Skeletal formula of diclofenamide
| image2 = Diclofenamide-3D-spacefill.png
| alt2 = Space-filling model of diclofenamide
| tradename =
| Drugs.com = {{drugs.com|international|diclofenamide}}
| MedlinePlus = a601233
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound = 55%
| metabolism =
| elimination_half-life =
| excretion =
| IUPHAR_ligand = 6807
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 120-97-8
| ATC_prefix = S01
| ATC_suffix = EC02
| ATC_supplemental =
| PubChem = 3038
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB01144
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2930
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VVJ6673MHY
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00518
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 101085
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 17
| C=6 | H=6 | Cl=2 | N=2 | O=4 | S=2
| smiles = Clc1c(cc(cc1Cl)S(=O)(=O)N)S(=O)(=O)N
| 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GJQPMPFPNINLKP-UHFFFAOYSA-N
| melting_point = 228.5
}}
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,{{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}}{{drugs.com|international|diclofenamide.html}}: Diclofenamide{{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 }} Subsequently, it was found effective in cases of therapy-resistant epilepsy.{{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 }} 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.{{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.{{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 }}
References
{{Reflist}}
{{Antiglaucoma preparations and miotics}}
Category:Carbonic anhydrase inhibitors