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Diclofenamide

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.

Diclofenamide
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa601233
ATC code
Pharmacokinetic data
Protein binding55%
Identifiers
  • 4,5-Dichlorobenzene-1,3-disulfonamide
CAS Number
  • 120-97-8 Y
PubChem CID
  • 3038
IUPHAR/BPS
  • 6807
DrugBank
  • DB01144 N
ChemSpider
  • 2930 Y
UNII
  • VVJ6673MHY
KEGG
  • D00518 Y
ChEBI
  • CHEBI:101085 Y
ChEMBL
  • ChEMBL17 Y
CompTox Dashboard (EPA)
  • DTXSID1022922
ECHA InfoCard100.004.037
Chemical and physical data
FormulaC6H6Cl2N2O4S2
Molar mass305.14 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point228.5 °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) Y
  • Key:GJQPMPFPNINLKP-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Uses edit

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 edit

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 edit

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

diclofenamide, dichlorphenamide, sulfonamide, carbonic, anhydrase, inhibitor, meta, disulfamoylbenzene, class, dichlorphenamide, carbonic, anhydrase, inhibitor, used, treatment, acute, angle, closure, glaucoma, while, dichlorphenamide, does, contain, sulfate, . 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 DiclofenamideClinical dataAHFS Drugs comInternational Drug NamesMedlinePlusa601233ATC codeS01EC02 WHO Pharmacokinetic dataProtein binding55 IdentifiersIUPAC name 4 5 Dichlorobenzene 1 3 disulfonamideCAS Number120 97 8 YPubChem CID3038IUPHAR BPS6807DrugBankDB01144 NChemSpider2930 YUNIIVVJ6673MHYKEGGD00518 YChEBICHEBI 101085 YChEMBLChEMBL17 YCompTox Dashboard EPA DTXSID1022922ECHA InfoCard100 004 037Chemical and physical dataFormulaC 6H 6Cl 2N 2O 4S 2Molar mass305 14 g mol 13D model JSmol Interactive imageMelting point228 5 C 443 3 F SMILES Clc1c cc cc1Cl S O O N S O O NInChI 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 YKey GJQPMPFPNINLKP UHFFFAOYSA N Y N Y what is this verify Uses editDiclofenamide 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 editIn 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 edit a b Dichlorphenaide Keveyis for Periodic Paralysis The Medical Letter April 16 2016 Retrieved December 19 2017 International Drug Names Diclofenamide 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 Rucquoy M Sorel L 1978 Diclofenamide in the treatment of therapy resistant epilepsy Acta Neurologica Belgica 78 3 174 82 PMID 352085 a b Johnson CY December 18 2017 This old drug was free Now it s 109 500 a year Washington Post nbsp This antihypertensive related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Diclofenamide amp oldid 1194457055, wikipedia, wiki, book, books, library,

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