U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DICHLORPHENAMIDE

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)

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KEVEYIS

Approved Use

Keveyis is an oral carbonic anhydrase inhibitor indicated for the treatment of primary hyperkalemic periodic paralysis, primary hypokalemic periodic paralysis, and related variants.

Launch Date

1958
Primary
KEVEYIS

Approved Use

Keveyis is an oral carbonic anhydrase inhibitor indicated for the treatment of primary hyperkalemic periodic paralysis, primary hypokalemic periodic paralysis, and related variants.

Launch Date

1958
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3030 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
66456 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
41 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
DICHLORPHENAMIDE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse 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%)
Weight loss (16.7%)
Itchy throat (16.7%)
Tachycardia (16.7%)
Gait instability (moderate, 16.7%)
Toothache (moderate, 16.7%)
Sources:
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
Hypokalemia
Metabolic acidosis
Fall
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Randomized trials of dichlorphenamide in the periodic paralyses. Working Group on Periodic Paralysis.
2000 Jan
Long-term management of a glaucomatous eye in a dog treated with medical therapy alone.
2001 Dec
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
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides.
2003 Mar 24
Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives.
2003 May 22
Carbonic anhydrase inhibitors are specific openers of skeletal muscle BK channel of K+-deficient rats.
2004 Apr
Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride.
2004 Jan 19
Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits.
2004 Jan 5
Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design.
2004 Jul 16
Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides.
2004 Jun 21
[Diclofenamide].
2005 Apr 15
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
A Korean family of hypokalemic periodic paralysis with mutation in a voltage-gated calcium channel (R1239G).
2005 Feb
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: 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
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
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents.
2007
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.
2007 Dec 1
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
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.
2008
Practical aspects in the management of hypokalemic periodic paralysis.
2008 Apr 21
Muscle channelopathies and electrophysiological approach.
2008 Jan
Treatment for periodic paralysis.
2008 Jan 23
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
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
Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate.
2009 Apr 23
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides.
2009 Jul 15
Biodegradable fumarate-based drug-delivery systems for ophthalmic applications.
2009 Mar 15
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
Increased expression of carbonic anhydrase I in the synovium of patients with ankylosing spondylitis.
2010 Dec 8

Sample Use Guides

Initial dose: 50 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:37:59 GMT 2023
Edited
by admin
on Fri Dec 15 15:37:59 GMT 2023
Record UNII
VVJ6673MHY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DICHLORPHENAMIDE
HSDB   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
DICHLORPHENAMIDE [USP IMPURITY]
Common Name English
diclofenamide [INN]
Common Name English
DICLOFENAMIDE [JAN]
Common Name English
DARANIDE
Brand Name English
DICLOFENAMIDE
INN   MART.   WHO-DD  
INN  
Official Name English
DICHLORPHENAMIDE [ORANGE BOOK]
Common Name English
DICHLORPHENAMIDE [USP-RS]
Common Name English
Diclofenamide [WHO-DD]
Common Name English
DICHLORPHENAMIDE [MI]
Common Name English
DICHLORPHENAMIDE [USP MONOGRAPH]
Common Name English
DICHLORPHENAMIDE [HSDB]
Common Name English
1,3-BENZENEDISULFONAMIDE, 4,5-DICHLORO-
Systematic Name English
DICLOFENAMIDE [MART.]
Common Name English
4,5-DICHLORO-M-BENZENEDISULFONAMIDE
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
EVMPD
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
DRUG BANK
DB01144
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PRIMARY
EPA CompTox
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
CAS
120-97-8
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PRIMARY
IUPHAR
6807
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PRIMARY
RXCUI
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
MERCK INDEX
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
PUBCHEM
3038
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PRIMARY
MESH
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
DRUG CENTRAL
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
ECHA (EC/EINECS)
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
FDA UNII
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
RS_ITEM_NUM
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
NCI_THESAURUS
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
DAILYMED
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
WIKIPEDIA
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
ChEMBL
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
HSDB
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
SMS_ID
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
INN
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
CHEBI
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
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY