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 |
---|---|---|---|---|
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 Date1958 |
|||
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 Date1958 |
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 |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
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: 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: 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 |
---|---|---|
Carbonic anhydrase inhibitors and osmotic agents in glaucoma. Carbonic anhydrase inhibitors. | 1968 Aug |
|
[Diclofenamide Reference Standard (Control 891) of National Institute of Hygienic Sciences]. | 1991 |
|
Generation and evaluation of a CYP2C9 heteroactivation pharmacophore. | 2003 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 |
|
Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor. | 2004 Jun |
|
Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. | 2005 Feb 15 |
|
Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? | 2005 Feb 15 |
|
Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with benzo[b]thiophene 1,1-dioxide sulfonamides. | 2005 Nov 1 |
|
Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori. | 2006 Apr 15 |
|
Carbonic anhydrase inhibitors ameliorate the symptoms of hypokalaemic periodic paralysis in rats by opening the muscular Ca2+-activated-K+ channels. | 2006 Jan |
|
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. | 2008 |
|
Muscle channelopathies and electrophysiological approach. | 2008 Jan |
|
Treatment for periodic paralysis. | 2008 Jan 23 |
|
Treatment of neuromuscular channelopathies: current concepts and future prospects. | 2008 Oct |
|
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 |
|
Increased expression of carbonic anhydrase I in the synovium of patients with ankylosing spondylitis. | 2010 Dec 8 |
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000175517
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
||
|
WHO-ATC |
S01EC02
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
||
|
EU-Orphan Drug |
EU/3/16/1677
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
||
|
FDA ORPHAN DRUG |
314210
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
||
|
NCI_THESAURUS |
C29577
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
||
|
WHO-VATC |
QS01EC02
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
||
|
NCI_THESAURUS |
C47796
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB07093MIG
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
DB01144
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
DTXSID1022922
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
120-97-8
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
6807
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
3353
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | RxNorm | ||
|
m4357
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | Merck Index | ||
|
3038
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
D004005
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
864
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
204-440-6
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
VVJ6673MHY
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
1188006
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
C65376
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
VVJ6673MHY
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
DICLOFENAMIDE
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
CHEMBL17
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
3267
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
100000082917
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
639
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY | |||
|
101085
Created by
admin on Fri Dec 15 15:37:59 GMT 2023 , Edited by admin on Fri Dec 15 15:37:59 GMT 2023
|
PRIMARY |
ACTIVE MOIETY