DICHLORPHENAMIDE

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)

HIDE SMILES / InChI

Molecular Formula	C6H6Cl2N2O4S2
Molecular Weight	305.159
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase 6	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Primary hyperkalemic periodic paralysis 1	Primary		Approved 8,429	KEVEYIS
Primary hypokalemic periodic paralysis 1	Primary		Approved 8,429	KEVEYIS

C_max

Value	Dose	Analyte	Population
3030 ng/mL	200 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
709 ng/mL	50 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
1512 ng/mL	100 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
2219 ng/mL	50 mg 2 times / day multiple, oral	DICHLORPHENAMIDE plasma	Homo sapiens
4867 ng/mL	100 mg 2 times / day multiple, oral	DICHLORPHENAMIDE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
66456 ng × h/mL	200 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
14734 ng × h/mL	50 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
28901 ng × h/mL	100 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
18329 ng × h/mL	50 mg 2 times / day multiple, oral	DICHLORPHENAMIDE plasma	Homo sapiens
37468 ng × h/mL	100 mg 2 times / day multiple, oral	DICHLORPHENAMIDE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
41 h	200 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
51.4 h	50 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens
31.9 h	100 mg single, oral	DICHLORPHENAMIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
12%			DICHLORPHENAMIDE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
400 mg 2 times / day multiple, oral Highest studied dose	healthy, 38.1±12.1	Disc. AE: Hypokalemia, Weight loss...
200 mg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Hypersensitivity, Hypokalemia...

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AEs

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AE	Significance	Dose	Population
Itchy throat	16.7% Disc. AE	400 mg 2 times / day multiple, oral Highest studied dose	healthy, 38.1±12.1
Tachycardia	16.7% Disc. AE	400 mg 2 times / day multiple, oral Highest studied dose	healthy, 38.1±12.1
Weight loss	16.7% Disc. AE	400 mg 2 times / day multiple, oral Highest studied dose	healthy, 38.1±12.1
Hypokalemia	mild, 83.3% Disc. AE	400 mg 2 times / day multiple, oral Highest studied dose	healthy, 38.1±12.1
Gait instability	moderate, 16.7% Disc. AE	400 mg 2 times / day multiple, oral Highest studied dose	healthy, 38.1±12.1

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587 inducer 781	substrate 1,037 inhibitor 1,767	substrate 1,217 inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599 CYP1A2 1,524 CYP2B6 810 CYP2C8 911 CYP2C19 1,478 P-gp 1,461 BCRP 699 OATP1B1 788 OATP1B3 706 OAT2 145 OAT4 146 OCT1 512 OCT2 647 MATE1 306 MATE2 263 OAT3 642	OAT1 326 OAT3 339 CYP1A2 1,054 CYP2B6 664 CYP2C8 693 CYP2C19 991 P-gp 1,537 BCRP 561 OATP1B1 406 OATP1B3 350 OAT2 115 OAT4 78 OCT1 327 OCT2 355 MATE1 135 MATE2 96	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Show entries

Target	Modality	Activity
BCRP 773	inhibitor 3,277	no
CYP1A2 1,692	inducer 1,573	no
CYP1A2 1,692	inhibitor 3,277	no
CYP2B6 1,001	inducer 1,573	no
CYP2B6 1,001	inhibitor 3,277	no

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Drug as victim

Show entries

Target	Modality	Activity
BCRP 561	substrate 3,367	no
CYP1A2 1,054	substrate 3,367	no
CYP2B6 664	substrate 3,367	no
CYP2C19 991	substrate 3,367	no
CYP2C8 693	substrate 3,367	no

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
001 Chemical	DY116256	https://www.001chemical.com/chem/120-97-8
3B Scientific (Wuhan) Corp	3B3-059238	http://www.3bsc.com/index/pro_info.php?id=98059
AA Blocks	AA000PYI	https://www.aablocks.com/goods/Goods/detail?id=AA000PYI
Aaron Chemicals	AR000QQA	http://www.aaronchem.com/120-97-8
abcr GmbH	AB547847	http://www.abcr.com/shop/en/AB547847

Showing 1 to 5 of 51 entries

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PubMed

PubMed

Show entries

Title	Date	PubMed
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides.	2003 Mar 24	12643899
Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits.	2004 Jan 5	14684332
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	16165351
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.	2005 Sep 1	16039848
Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited--old leads for new applications?	2008 Jul 21	18600270