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

Details

Stereochemistry ACHIRAL
Molecular Formula C9H10N2O3S2
Molecular Weight 258.3198
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHOXZOLAMIDE

SMILES

CCOc1ccc2c(c1)sc(n2)S(=O)(=O)N

InChI

InChIKey=OUZWUKMCLIBBOG-UHFFFAOYSA-N
InChI=1S/C9H10N2O3S2/c1-2-14-6-3-4-7-8(5-6)15-9(11-7)16(10,12)13/h3-5H,2H2,1H3,(H2,10,12,13)

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=011047

Ethoxzolamide is a carbonic anhydrase I inhibitor. It is used in the treatment of glaucoma and duodenal ulcers, and as a diuretic. Ethoxzolamide was marketed under trade name Cadrase, but is now discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CARDRASE

Approved Use

Ethoxzolamide is a carbonic anhydrase inhibitor used as diuretic and in glaucoma.
Primary
CARDRASE

Approved Use

Ethoxzolamide is a carbonic anhydrase inhibitor used as diuretic and in glaucoma.
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
300 min
, oral
ETHOXZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
11%
unknown, unknown
ETHOXZOLAMIDE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
4%
, oral
ETHOXZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
250 mg 4 times / day multiple, oral
Highest studied dose
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
500 mg 1 times / day multiple, oral
Recommended
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
Disc. AE: Diarrhea, Paresthesia...
AEs leading to
discontinuation/dose reduction:
Diarrhea (15.4%)
Paresthesia (7.7%)
Fatigue (7.7%)
Weakness (7.7%)
Leg cramps (7.7%)
Abdominal cramps (7.7%)
Sources:
125 mg 6 times / day multiple, oral
Recommended
Dose: 125 mg, 6 times / day
Route: oral
Route: multiple
Dose: 125 mg, 6 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Disc. AE: Muscle cramps, Dizziness...
AEs leading to
discontinuation/dose reduction:
Muscle cramps (severe, 5.5%)
Dizziness (severe, 5.5%)
Generalized eruption (severe, 5.5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 15.4%
Disc. AE
500 mg 1 times / day multiple, oral
Recommended
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
Abdominal cramps 7.7%
Disc. AE
500 mg 1 times / day multiple, oral
Recommended
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
Fatigue 7.7%
Disc. AE
500 mg 1 times / day multiple, oral
Recommended
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
Leg cramps 7.7%
Disc. AE
500 mg 1 times / day multiple, oral
Recommended
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
Paresthesia 7.7%
Disc. AE
500 mg 1 times / day multiple, oral
Recommended
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
Weakness 7.7%
Disc. AE
500 mg 1 times / day multiple, oral
Recommended
Dose: 500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg, 1 times / day
Sources:
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
Dizziness severe, 5.5%
Disc. AE
125 mg 6 times / day multiple, oral
Recommended
Dose: 125 mg, 6 times / day
Route: oral
Route: multiple
Dose: 125 mg, 6 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Generalized eruption severe, 5.5%
Disc. AE
125 mg 6 times / day multiple, oral
Recommended
Dose: 125 mg, 6 times / day
Route: oral
Route: multiple
Dose: 125 mg, 6 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Muscle cramps severe, 5.5%
Disc. AE
125 mg 6 times / day multiple, oral
Recommended
Dose: 125 mg, 6 times / day
Route: oral
Route: multiple
Dose: 125 mg, 6 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [EC50 5.8 uM]
yes
PubMed

PubMed

TitleDatePubMed
Carbonic anhydrase inhibitors. Inhibition of red blood cell ostrich (Struthio camelus) carbonic anhydrase with a series of aromatic and heterocyclic sulfonamides.
2005 Aug
Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors.
2005 Dec 1
Transport activity of MCT1 expressed in Xenopus oocytes is increased by interaction with carbonic anhydrase.
2005 Dec 2
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
Modulation of carbonic anhydrase activity in two nitrogen fixing cyanobacteria, Nostoc calcicola and Anabaena sp.
2005 Oct
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.
2005 Sep 1
Expression, purification, kinetic, and structural characterization of an alpha-class carbonic anhydrase from Aedes aegypti (AaCA1).
2006 Aug
Cryptococcus neoformans senses CO2 through the carbonic anhydrase Can2 and the adenylyl cyclase Cac1.
2006 Jan
Carbonic anhydrase inhibitors ameliorate the symptoms of hypokalaemic periodic paralysis in rats by opening the muscular Ca2+-activated-K+ channels.
2006 Jan
Effect of human carbonic anhydrase II on the activity of the human electrogenic Na/HCO3 cotransporter NBCe1-A in Xenopus oocytes.
2006 Jul 14
Heterogeneous origin of carbonic anhydrase activity of thylakoid membranes.
2006 May
Pea leaf thylakoids contain several carbonic anhydrases.
2006 May-Jun
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents.
2007
Inhibition of hypoxia-induced calcium responses in pulmonary arterial smooth muscle by acetazolamide is independent of carbonic anhydrase inhibition.
2007 Apr
Acclimation of wild-type cells and CO2-insensitive mutants of the green alga Chlorella ellipsoidea to elevated [CO2].
2007 Aug
Direct non-cyclooxygenase-2 targets of celecoxib and their potential relevance for cancer therapy.
2007 Dec 3
Pulmonary vasodilation by acetazolamide during hypoxia is unrelated to carbonic anhydrase inhibition.
2007 Jan
Electrical parameters and ion species for active transport in human esophageal stratified squamous epithelium and Barrett's specialized columnar epithelium.
2007 Jul
Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors.
2007 Jul 1
Carbonic anhydrase II increases the activity of the human electrogenic Na+/HCO3- cotransporter.
2007 May 4
The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets.
2008
Carbonic anhydrase inhibitors: the X-ray crystal structure of ethoxzolamide complexed to human isoform II reveals the importance of thr200 and gln92 for obtaining tight-binding inhibitors.
2008 Apr 15
Lack of aquaporin-4 water transport inhibition by antiepileptics and arylsulfonamides.
2008 Aug 1
Fluid and osmolyte recovery in the common pond snail Lymnaea stagnalis following full-body withdrawal.
2008 Feb
Antagonistic effect of juvenile hormone on hemocyte-spreading behavior of Spodoptera exigua in response to an insect cytokine and its putative membrane action.
2008 Jun
The bicarbonate transporter is essential for Bacillus anthracis lethality.
2008 Nov
QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software.
2009 Apr
A pea mutant (costata) expressing higher activity in thylakoid membrane-bound carbonic anhydrase alters PSII downregulation mechanisms.
2009 Aug
Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c.
2009 Dec 1
Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates.
2009 Feb 1
Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference.
2009 Feb 1
Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties.
2009 Feb 17
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides.
2009 Jul 15
Measurement of nanomolar dissociation constants by titration calorimetry and thermal shift assay - radicicol binding to Hsp90 and ethoxzolamide binding to CAII.
2009 Jun 10
Titration calorimetry standards and the precision of isothermal titration calorimetry data.
2009 Jun 18
Manganese-dependent carboanhydrase activity of photosystem II proteins.
2009 May
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis.
2009 May 14
Saccharomyces cerevisiae β-carbonic anhydrase: inhibition and activation studies.
2010
Cyclodextrins in delivery systems: Applications.
2010 Apr
Nonenzymatic augmentation of lactate transport via monocarboxylate transporter isoform 4 by carbonic anhydrase II.
2010 Apr
Carbonic anhydrase inhibitors. The beta-carbonic anhydrases from the fungal pathogens Cryptococcus neoformans and Candida albicans are strongly inhibited by substituted-phenyl-1H-indole-5-sulfonamides.
2010 Apr 15
Differences in transcription between free-living and CO2-activated third-stage larvae of Haemonchus contortus.
2010 Apr 27
Sharpey-Schafer lecture: gas channels.
2010 Dec
T tubules and surface membranes provide equally effective pathways of carbonic anhydrase-facilitated lactic acid transport in skeletal muscle.
2010 Dec 13
Increased expression of carbonic anhydrase I in the synovium of patients with ankylosing spondylitis.
2010 Dec 8
Ocular inserts - Advancement in therapy of eye diseases.
2010 Jul
Alterations in osteoclast function and phenotype induced by different inhibitors of bone resorption--implications for osteoclast quality.
2010 Jun 1
Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis.
2010 Mar 11
Carbonic anhydrase II regulates differentiation of ameloblasts via intracellular pH-dependent JNK signaling pathway.
2010 Nov
Role of carbonic anhydrase IV in the bicarbonate-mediated activation of murine and human sperm.
2010 Nov 24
Patents

Sample Use Guides

Ethoxzolamide tablets are indicated for oral administration. For treatment of glaucoma, ethoxzolamide was used at 62.5 mg. b.i.d.
Route of Administration: Oral
Inhibition of human carbonic anhydrases was measured using a stop-floww assay monitoring the physiological reaction (CO2 hydration to bicarbonate). Ethoxzolamide is a relatively non-selective carbonic anhydrase (CA) inhibitor. It inhibits CA I, II, IV, VA, VB, VII, IX, XII, XIV with Ki 0.8-93 nM.
Name Type Language
ETHOXZOLAMIDE
HSDB   MI   ORANGE BOOK   USP-RS   WHO-DD  
Common Name English
ETHOXZOLAMIDE [ORANGE BOOK]
Common Name English
CARDRASE
Brand Name English
2-BENZOTHIAZOLESULFONAMIDE, 6-ETHOXY-
Systematic Name English
NSC-10679
Code English
ETHOXZOLAMIDE [HSDB]
Common Name English
ETHAMIDE
Brand Name English
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE
Systematic Name English
ETHOXZOLAMIDE [MI]
Common Name English
ETHOXZOLAMIDE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29577
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
NCI_THESAURUS C448
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
Code System Code Type Description
PUBCHEM
3295
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
EPA CompTox
452-35-7
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL18
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
MERCK INDEX
M5079
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00311
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
EVMPD
SUB13739MIG
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
WIKIPEDIA
ETHOXZOLAMIDE
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
HSDB
3268
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
FDA UNII
Z52H4811WX
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
IUPHAR
6814
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
CAS
452-35-7
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
MESH
D005016
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
NCI_THESAURUS
C65561
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-199-5
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY
DRUG CENTRAL
1089
Created by admin on Sat Jun 26 06:18:07 UTC 2021 , Edited by admin on Sat Jun 26 06:18:07 UTC 2021
PRIMARY