Ethoxzolamide

Summary

Ethoxzolamide (CHEMBL18) is an approved small-molecule EC 4.2.1.1 (carbonic anhydrase) inhibitor targeting CA1, CA14, and CA12.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Targets: 4 (CA1, CA14, CA12…)
• Chemistry: 258.3 Da · C9H10N2O3S2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL18
Name	Ethoxzolamide
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	3295
ChEBI	CHEBI:101096
Molecular formula	C9H10N2O3S2
Molecular weight	258.3
InChIKey	OUZWUKMCLIBBOG-UHFFFAOYSA-N

SMILES: CCOC1=CC2=C(C=C1)N=C(S2)S(=O)(=O)N

IUPAC name: 6-ethoxy-1,3-benzothiazole-2-sulfonamide

ChEBI definition: A sulfonamide that is 1,3-benzothiazole-2-sulfonamide which is substituted by an ethoxy group at position 6. A carbonic anhydrase inhibitor, it has been used in the treatment of glaucoma, and as a diuretic.

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

Also known as: Cardrase, Ethamide, Ethoxzolamide, NSC-10679, ethoxzolamide, ethoxazolamide, Ethoxazolamide, etoxzolamide, SID29215007, SID855751, ETHOXZOLAMIDE, SID104171380

Parent form; salt/anhydrous children: CHEMBL6146662

Patent coverage: 843 distinct patent families (3,042 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 3,026 (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	7.6	0%	P00915
CA14	carbonic anhydrase 14	Inhibition	7.6	0%	Q9ULX7
CA12	carbonic anhydrase 12	Inhibition	7.66	0.2%	O43570
CA7	carbonic anhydrase 7	Inhibition	9.1	1.6%	P43166

Broader ChEMBL bioactivity targets: 30 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Pyruvate kinase PKM, Lysine-specific demethylase 4E, Prelamin-A/C, Histone-lysine N-methyltransferase 2A, Carbonic anhydrase 3, Beta-lactamase, Carbonic anhydrase 2, Carbonic anhydrase V, Carbonic anhydrase 13.

Bioactivity

ChEMBL activities: 399 potent at pChembl ≥ 5 of 408 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CA9	9.6	IC50	0.25	nM	CHEMBL_ACT_19104140
CA2	9.52	IC50	0.3	nM	CHEMBL_ACT_13344575
CA2	9.4	IC50	0.4	nM	CHEMBL_ACT_276421
CA2	9.31	Ki	0.49	nM	CHEMBL_ACT_276422
CA7	9.15	Kd	0.71	nM	CHEMBL_ACT_12696176
CA7	9.15	Kd	0.71	nM	CHEMBL_ACT_13509967
CA2	9.15	Kd	0.71	nM	CHEMBL_ACT_13510053
CA7	9.11	Ki	0.78	nM	CHEMBL_ACT_1435545
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_13407601
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_13440686
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_13859517
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_1780605
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_2056572
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_2159091
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_2287531
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_2491997
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_3310903
CA7	9.1	Ki	0.8	nM	CHEMBL_ACT_6223166
CA9	9	IC50	0.99	nM	CHEMBL_ACT_13344560
CA2	8.96	Kd	1.1	nM	CHEMBL_ACT_12696207
CA5A	8.7	Ki	2	nM	CHEMBL_ACT_1520948
CA14	8.6	Ki	2.5	nM	CHEMBL_ACT_13859493
CA14	8.6	Ki	2.5	nM	CHEMBL_ACT_2492025
CA14	8.6	Ki	2.5	nM	CHEMBL_ACT_29230175
CA14	8.6	Ki	2.5	nM	CHEMBL_ACT_6311512
CA2	8.52	IC50	3	nM	CHEMBL_ACT_1045305
CA2	8.52	IC50	3	nM	CHEMBL_ACT_1297399
CA2	8.32	IC50	4.83	nM	CHEMBL_ACT_19104108
CA2	8.27	Ki	5.4	nM	CHEMBL_ACT_1520947
CA2	8.1	Ki	8	nM	CHEMBL_ACT_1003708

Target pathways

Aggregated over 4 target gene(s): CA1, CA14, CA12, CA7.

Top Reactome pathways

12 total, by targets touching each:

Pathway	Targets	Genes
Metabolism	4	CA1, CA12, CA14, CA7
Reversible hydration of carbon dioxide	4	CA1, CA12, CA14, CA7
Erythrocytes take up carbon dioxide and release oxygen	1	CA1
Erythrocytes take up oxygen and release carbon dioxide	1	CA1
Cytokine Signaling in Immune system	1	CA1
O2/CO2 exchange in erythrocytes	1	CA1
Immune System	1	CA1
Transport of small molecules	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
estrous cycle	1
chloride ion homeostasis	1
positive regulation of synaptic transmission, GABAergic	1
obsolete positive regulation of cellular pH reduction	1
regulation of intracellular pH	1
neuron cellular homeostasis	1
regulation of chloride transport	1

Indications & clinical

Indications

0 indications (0 at ChEMBL trial phase 4).

Clinical trials

Total trials: 0.

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.

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

Molecule	Source	Status	Shared targets
ACETAMINOPHEN	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
ACETAZOLAMIDE	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
CELECOXIB	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
CHLORTHALIDONE	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
COUMARIN	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
DICHLORPHENAMIDE	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
DOBUTAMINE	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
FUROSEMIDE	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
LACOSAMIDE	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
SALICYLIC ACID	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12, CA14, CA7
BORTEZOMIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
BRINZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
DORZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
FAMOTIDINE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
IMATINIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
INDAPAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
LEVETIRACETAM	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
MAFENIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
METHAZOLAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
NILOTINIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
SULFANILAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
TOPIRAMATE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
TRICHLORMETHIAZIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
TRIENTINE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
VALDECOXIB	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
VERALIPRIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
ZONISAMIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14, CA7
CAFFEIC ACID	ChEMBL	Phase 3	CA1, CA12, CA14, CA7
CURCUMIN	ChEMBL	Phase 3	CA1, CA12, CA14, CA7
QUERCETIN	ChEMBL	Phase 3	CA1, CA12, CA14, CA7
RESVERATROL	ChEMBL	Phase 3	CA1, CA12, CA14, CA7
SACCHARIN	ChEMBL	Phase 3	CA1, CA12, CA14, CA7
SPERMIDINE	ChEMBL	Phase 3	CA1, CA12, CA14, CA7
CARZENIDE	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
COUMAPHOS	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
ELLAGIC ACID	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
GALLIC ACID	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
INDISULAM	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
IROSUSTAT	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
PCI-27483	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
SONEPIPRAZOLE	ChEMBL	Phase 2	CA1, CA12, CA14, CA7
HYDROQUINONE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14
PHENOL	ChEMBL	Phase 4 (approved)	CA1, CA12, CA14
PYRITHIONE ZINC	ChEMBL	Phase 4 (approved)	CA12, CA14, CA7
SULPIRIDE	ChEMBL	Phase 4 (approved)	CA1, CA12, CA7
P-TOLUENESULFONAMIDE	ChEMBL	Phase 3	CA1, CA12, CA7
THIMEROSAL	ChEMBL	Phase 3	CA12, CA14, CA7
SODIUM CYCLAMATE	ChEMBL	Phase 2	CA12, CA14, CA7
SULFASUCCINAMIDE	ChEMBL	Phase 2	CA1, CA12, CA14
HYDROCHLOROTHIAZIDE	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA14
PAZOPANIB	ChEMBL + PubChem	Phase 4 (approved)	CA1, CA12
SULTHIAME	ChEMBL	Phase 4 (approved)	CA1, CA7
ZOLEDRONIC ACID	ChEMBL	Phase 4 (approved)	CA12, CA14
PRITELIVIR	ChEMBL	Phase 3	CA1, CA12
BENZYLSULFAMIDE	ChEMBL	Phase 2	CA1, CA12
DAIDZEIN	ChEMBL	Phase 2	CA12, CA7
DITIOCARB	ChEMBL	Phase 2	CA1, CA12
FLAVONE	ChEMBL	Phase 2	CA1, CA12
ISOQUERCETIN	ChEMBL	Phase 2	CA12, CA7
LUTEOLIN	ChEMBL	Phase 2	CA12, CA7