Dichlorphenamide

Summary

Dichlorphenamide (CHEMBL17) is an approved small-molecule EC 4.2.1.1 (carbonic anhydrase) inhibitor (ATC S01EC02) targeting CA1, CA4, and CA12; indicated across 4 conditions including glaucoma and myotonic syndrome.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: S01EC02
• Targets: 3 (CA1, CA4, CA12)
• Indications: 4 conditions
• Clinical trials: 2
• Chemistry: 305.2 Da · C6H6Cl2N2O4S2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL17
Name	Dichlorphenamide
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	3038
ChEBI	CHEBI:101085
ATC	S01EC02
Molecular formula	C6H6Cl2N2O4S2
Molecular weight	305.2
InChIKey	GJQPMPFPNINLKP-UHFFFAOYSA-N

SMILES: C1=C(C=C(C(=C1S(=O)(=O)N)Cl)Cl)S(=O)(=O)N

IUPAC name: 4,5-dichlorobenzene-1,3-disulfonamide

ChEBI definition: A sulfonamide that is benzene-1,3-disulfonamide in which the hydrogens at positions 4 and 5 are substituted by chlorine. An oral carbonic anhydrase inhibitor, it partially suppresses the secretion (inflow) of aqueous humor in the eye and so reduces intraocular pressure. It is used for the treatment of glaucoma.

Pharmacological roles (ChEBI): EC 4.2.1.1 (carbonic anhydrase) inhibitor, antiglaucoma drug, ophthalmology drug.

Also known as: Daranide, Dichlorphenamide, Diclofenamida, Diclofenamide, Keveyis, Oratrol, dichlorophenamide, dichlorphenamide, Dichlorophenamide, dichorophenamide, Dichorophenamide, SID11112264

Patent coverage: 2,344 distinct patent families (9,022 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 8,909 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
CA1	carbonic anhydrase 1	Inhibition	7.13	0%	P00915
CA4	carbonic anhydrase 4	Inhibition	4.82	0.3%	P22748
CA12	carbonic anhydrase 12	Inhibition	7.3	0.2%	O43570

Broader ChEMBL bioactivity targets: 22 (assay-derived). Sample: Prelamin-A/C, Carbonic anhydrase 2, Carbonic anhydrase 13, Carbonic anhydrase 7, Carbonic anhydrase 1, Carbonic anhydrase 4, Carbonic anhydrase 6, Carbonic anhydrase 12, Cytochrome P450 2C9, Carbonic anhydrase 14.

Bioactivity

ChEMBL activities: 328 potent at pChembl ≥ 5 of 333 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CA7	8.22	Ki	6	nM	CHEMBL_ACT_2159090
CA2	8.1	Ki	8	nM	CHEMBL_ACT_1435148
CA2	8.05	Ki	9	nM	CHEMBL_ACT_2159056
CA5B	7.68	Ki	21	nM	CHEMBL_ACT_1655281
CA5B	7.68	Ki	21	nM	CHEMBL_ACT_1780629
CA5B	7.68	Ki	21	nM	CHEMBL_ACT_2056557
CA5B	7.68	Ki	21	nM	CHEMBL_ACT_3393265
CA5B	7.68	Ki	21	nM	CHEMBL_ACT_5236269
Q9D6N1	7.64	Ki	23	nM	CHEMBL_ACT_1435963
Q9D6N1	7.64	Ki	23	nM	CHEMBL_ACT_1780634
Q9D6N1	7.64	Ki	23	nM	CHEMBL_ACT_2056592
Q9D6N1	7.64	Ki	23	nM	CHEMBL_ACT_3393270
Q9D6N1	7.64	Ki	23	nM	CHEMBL_ACT_60267
CA13	7.64	Ki	23	nM	CHEMBL_ACT_6262815
CA1	7.6	Ki	25	nM	CHEMBL_ACT_1435147
CA7	7.58	Ki	26.5	nM	CHEMBL_ACT_13859508
CA7	7.58	Ki	26.5	nM	CHEMBL_ACT_1435962
CA7	7.58	Ki	26	nM	CHEMBL_ACT_1780630
CA7	7.58	Ki	26	nM	CHEMBL_ACT_2056571
CA7	7.58	Ki	26	nM	CHEMBL_ACT_3393267
CA7	7.58	Ki	26	nM	CHEMBL_ACT_6262810
CA9	7.47	Ki	34	nM	CHEMBL_ACT_1435149
CA2	7.42	Ki	38	nM	CHEMBL_ACT_1042470
CA2	7.42	Ki	38	nM	CHEMBL_ACT_10946398
CA2	7.42	Ki	38	nM	CHEMBL_ACT_12083959
CA2	7.42	Ki	38	nM	CHEMBL_ACT_1264410
CA2	7.42	Ki	38	nM	CHEMBL_ACT_12655983
CA2	7.42	Ki	38	nM	CHEMBL_ACT_13286815
CA2	7.42	Ki	38	nM	CHEMBL_ACT_13866458
CA2	7.42	Ki	38	nM	CHEMBL_ACT_13872676

Target pathways

Aggregated over 3 target gene(s): CA1, CA4, CA12.

Top Reactome pathways

12 total, by targets touching each:

Pathway	Targets	Genes
Metabolism	3	CA1, CA12, CA4
Reversible hydration of carbon dioxide	3	CA1, CA12, CA4
Erythrocytes take up carbon dioxide and release oxygen	2	CA1, CA4
Erythrocytes take up oxygen and release carbon dioxide	2	CA1, CA4
O2/CO2 exchange in erythrocytes	2	CA1, CA4
Transport of small molecules	2	CA1, CA4
Cytokine Signaling in Immune system	1	CA1
Immune System	1	CA1
Interleukin-12 family signaling	1	CA1
Signaling by Interleukins	1	CA1
Gene and protein expression by JAK-STAT signaling after Interleukin-12 stimulation	1	CA1
Interleukin-12 signaling	1	CA1

Dominant GO biological processes

GO term	Targets
response to fructose	1
bicarbonate transport	1
estrous cycle	1
chloride ion homeostasis	1

Indications & clinical

Indications

4 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
glaucoma	4	MONDO:0005041	MONDO:0005041
myotonic syndrome	3	MONDO:0016120	MONDO:0008195
hypokalemic periodic paralysis	3	MONDO:0008223	MONDO:0008223
hyperkalemic periodic paralysis	3	MONDO:0008224	MONDO:0008224

Clinical trials

Total trials: 2.

Phase distribution

Phase	Trials
PHASE3	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00004802	PHASE3	COMPLETED	Phase III Randomized, Double-Blind, Placebo-Controlled Study of Dichlorphenamide for Periodic Paralyses and Associated Sodium Channel Disorders
NCT00494507	PHASE3	COMPLETED	Hyper- and Hypokalemic Periodic Paralysis Study

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

87 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
ACETAMINOPHEN	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
ACETAZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
BORTEZOMIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
BRINZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
CELECOXIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
CHLORTHALIDONE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
COUMARIN	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
DOBUTAMINE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
DORZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
ETHOXZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
FAMOTIDINE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
FUROSEMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
HYDROQUINONE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
IMATINIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
INDAPAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
LACOSAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
LEVETIRACETAM	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
MAFENIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
METHAZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
NILOTINIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
PHENOL	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
SALICYLIC ACID	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
SULFANILAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
TOPIRAMATE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
TRICHLORMETHIAZIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
TRIENTINE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
VALDECOXIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
VERALIPRIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
ZONISAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA4
CAFFEIC ACID	ChEMBL	Phase 3	CA1, CA12, CA4
CURCUMIN	ChEMBL	Phase 3	CA1, CA12, CA4
QUERCETIN	ChEMBL	Phase 3	CA1, CA12, CA4
RESVERATROL	ChEMBL	Phase 3	CA1, CA12, CA4
SACCHARIN	ChEMBL	Phase 3	CA1, CA12, CA4
SPERMIDINE	ChEMBL	Phase 3	CA1, CA12, CA4
COUMAPHOS	ChEMBL	Phase 2	CA1, CA12, CA4
DITIOCARB	ChEMBL	Phase 2	CA1, CA12, CA4
ELLAGIC ACID	ChEMBL	Phase 2	CA1, CA12, CA4
GALLIC ACID	ChEMBL	Phase 2	CA1, CA12, CA4
IROSUSTAT	ChEMBL	Phase 2	CA1, CA12, CA4
PCI-27483	ChEMBL	Phase 2	CA1, CA12, CA4
SONEPIPRAZOLE	ChEMBL	Phase 2	CA1, CA12, CA4
SULFASUCCINAMIDE	ChEMBL	Phase 2	CA1, CA12, CA4
PAZOPANIB	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12
PYRITHIONE ZINC	ChEMBL	Phase 4 (approved)	CA12, CA4
SODIUM	ChEMBL	Phase 4 (approved)	CA1, CA4
SULPIRIDE	ChEMBL	Phase 4 (approved)	CA1, CA12
P-TOLUENESULFONAMIDE	ChEMBL	Phase 3	CA1, CA12
PRITELIVIR	ChEMBL	Phase 3	CA1, CA12
THIMEROSAL	ChEMBL	Phase 3	CA12, CA4
BENZYLSULFAMIDE	ChEMBL	Phase 2	CA1, CA12
CARZENIDE	ChEMBL	Phase 2	CA1, CA12
DAIDZEIN	ChEMBL	Phase 2	CA12, CA4
FLAVONE	ChEMBL	Phase 2	CA1, CA12
INDISULAM	ChEMBL	Phase 2	CA1, CA12
ISOQUERCETIN	ChEMBL	Phase 2	CA12, CA4
LUTEOLIN	ChEMBL	Phase 2	CA12, CA4
PROPAZOLAMIDE	ChEMBL	Phase 2	CA1, CA4
Sodium Carbonate	PubChem	Approved	CA1, CA4
CHLOROTHIAZIDE	ChEMBL	Phase 4 (approved)	CA1