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)
Molecular Formula | C6H6Cl2N2O4S2 |
Molecular Weight | 305.159 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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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 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 |
|
Generation and evaluation of a CYP2C9 heteroactivation pharmacophore. | 2003 Dec |
|
Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride. | 2004 Jan 19 |
|
Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor. | 2004 Jun |
|
Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides. | 2004 Jun 21 |
|
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation. | 2005 Aug |
|
Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. | 2005 Feb 15 |
|
Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. | 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 |
|
[Diuretic therapy in heart failure]. | 2006 Jan-Feb |
|
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 |
|
Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited--old leads for new applications? | 2008 Jul 21 |
|
Acetazolamide prevents vacuolar myopathy in skeletal muscle of K(+) -depleted rats. | 2008 May |
|
Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. | 2009 Apr 23 |
|
Increased expression of carbonic anhydrase I in the synovium of patients with ankylosing spondylitis. | 2010 Dec 8 |
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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on
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Record UNII |
VVJ6673MHY
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Record Status |
Validated (UNII)
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Record Version |
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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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100000082917
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |