Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H6Cl2N2O4S2 |
Molecular Weight | 305.159 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NS(=O)(=O)C1=CC(=C(Cl)C(Cl)=C1)S(N)(=O)=O
InChI
InChIKey=GJQPMPFPNINLKP-UHFFFAOYSA-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)
DescriptionCurator's Comment: description was created based on several sources, including https://www.urmc.rochester.edu/news/story/4461/new-drug-for-periodic-paralysis-has-roots-in-urmc-research.aspx
Curator's Comment: description was created based on several sources, including https://www.urmc.rochester.edu/news/story/4461/new-drug-for-periodic-paralysis-has-roots-in-urmc-research.aspx
Diclorphenamide, a carbonic anhydrase inhibitor, was initially developed for the treatment of glaucome, however, now it is used for patients suffering from primary hypokalemic and hyperkalemic periodic paralysis. The exact mechanism of diclorphenamide in periodic paralysis is unknown.
Originator
Sources: https://www.urmc.rochester.edu/news/story/4461/new-drug-for-periodic-paralysis-has-roots-in-urmc-research.aspx
Curator's Comment: # Merck & Co
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095180 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | KEVEYIS Approved UseKeveyis is an oral carbonic anhydrase inhibitor indicated for the treatment of primary hyperkalemic periodic paralysis, primary hypokalemic periodic paralysis, and related variants. Launch Date-3.61238397E11 |
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Primary | KEVEYIS Approved UseKeveyis is an oral carbonic anhydrase inhibitor indicated for the treatment of primary hyperkalemic periodic paralysis, primary hypokalemic periodic paralysis, and related variants. Launch Date-3.61324806E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3030 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29762909 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICHLORPHENAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
66456 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29762909 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICHLORPHENAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
41 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29762909 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICHLORPHENAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12% |
DICHLORPHENAMIDE plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, 38.1±12.1 n = 6 Health Status: healthy Age Group: 38.1±12.1 Sex: M+F Population Size: 6 Sources: |
Disc. AE: Hypokalemia, Weight loss... AEs leading to discontinuation/dose reduction: Hypokalemia (mild, 83.3%) Sources: Weight loss (16.7%) Itchy throat (16.7%) Tachycardia (16.7%) Gait instability (moderate, 16.7%) Toothache (moderate, 16.7%) |
200 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Primary hyperkalemic periodic paralysis|Primary hypokalemic periodic paralysis Sources: |
Disc. AE: Hypersensitivity, Hypokalemia... AEs leading to discontinuation/dose reduction: Hypersensitivity Sources: Hypokalemia Metabolic acidosis Fall |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Itchy throat | 16.7% Disc. AE |
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, 38.1±12.1 n = 6 Health Status: healthy Age Group: 38.1±12.1 Sex: M+F Population Size: 6 Sources: |
Tachycardia | 16.7% Disc. AE |
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, 38.1±12.1 n = 6 Health Status: healthy Age Group: 38.1±12.1 Sex: M+F Population Size: 6 Sources: |
Weight loss | 16.7% Disc. AE |
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, 38.1±12.1 n = 6 Health Status: healthy Age Group: 38.1±12.1 Sex: M+F Population Size: 6 Sources: |
Hypokalemia | mild, 83.3% Disc. AE |
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, 38.1±12.1 n = 6 Health Status: healthy Age Group: 38.1±12.1 Sex: M+F Population Size: 6 Sources: |
Gait instability | moderate, 16.7% Disc. AE |
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, 38.1±12.1 n = 6 Health Status: healthy Age Group: 38.1±12.1 Sex: M+F Population Size: 6 Sources: |
Toothache | moderate, 16.7% Disc. AE |
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, 38.1±12.1 n = 6 Health Status: healthy Age Group: 38.1±12.1 Sex: M+F Population Size: 6 Sources: |
Fall | Disc. AE | 200 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Primary hyperkalemic periodic paralysis|Primary hypokalemic periodic paralysis Sources: |
Hypersensitivity | Disc. AE | 200 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Primary hyperkalemic periodic paralysis|Primary hypokalemic periodic paralysis Sources: |
Hypokalemia | Disc. AE | 200 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Primary hyperkalemic periodic paralysis|Primary hypokalemic periodic paralysis Sources: |
Metabolic acidosis | Disc. AE | 200 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Primary hyperkalemic periodic paralysis|Primary hypokalemic periodic paralysis Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 5.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 9.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 9.0 |
no | |||
Page: 6.0 |
yes | |||
Page: 6.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Long-term management of a glaucomatous eye in a dog treated with medical therapy alone. | 2001 Dec |
|
Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. | 2003 Mar 10 |
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Carbonic anhydrase inhibitors are specific openers of skeletal muscle BK channel of K+-deficient rats. | 2004 Apr |
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Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. | 2004 Jan 5 |
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Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor. | 2004 Jun |
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Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. | 2005 Sep 1 |
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Carbonic anhydrase inhibitors ameliorate the symptoms of hypokalaemic periodic paralysis in rats by opening the muscular Ca2+-activated-K+ channels. | 2006 Jan |
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Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs. | 2006 Mar 23 |
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Carbonic anhydrase inhibitors: clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue. | 2006 Nov 30 |
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The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents. | 2007 |
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Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. | 2007 Jan 25 |
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The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. | 2008 |
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Treatment for periodic paralysis. | 2008 Jan 23 |
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Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited--old leads for new applications? | 2008 Jul 21 |
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QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software. | 2009 Apr |
|
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. | 2009 May 14 |
|
Evaluation of the therapeutic potential of carbonic anhydrase inhibitors in two animal models of dystrophin deficient muscular dystrophy. | 2009 Nov 1 |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175517
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WHO-ATC |
S01EC02
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EU-Orphan Drug |
EU/3/16/1677
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FDA ORPHAN DRUG |
314210
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NCI_THESAURUS |
C29577
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WHO-VATC |
QS01EC02
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NCI_THESAURUS |
C47796
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SUB07093MIG
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DB01144
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3353
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m4357
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3038
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C65376
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VVJ6673MHY
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DICLOFENAMIDE
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CHEMBL17
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3267
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100000082917
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639
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101085
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ACTIVE MOIETY