Diclofenamide

Last updated
Diclofenamide
Diclofenamide.svg
Diclofenamide-3D-spacefill.png
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a601233
ATC code
Pharmacokinetic data
Protein binding 55%
Identifiers
  • 4,5-Dichlorobenzene-1,3-disulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.037 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C6H6Cl2N2O4S2
Molar mass 305.14 g·mol−1
3D model (JSmol)
Melting point 228.5 °C (443.3 °F)
  • Clc1c(cc(cc1Cl)S(=O)(=O)N)S(=O)(=O)N
  • 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) Yes check.svgY
  • Key:GJQPMPFPNINLKP-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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.

Contents

Uses

Diclofenamide was approved in the United States in 1958 as Daranide to treat glaucoma, [1] [2] [3] Subsequently, it was found effective in cases of therapy-resistant epilepsy. [4] 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. [1] [5]

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 ] 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. [5]

References

  1. 1 2 "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. 1 2 Johnson CY (December 18, 2017). "This old drug was free. Now it's $109,500 a year". Washington Post.
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