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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10N2O3S2
Molecular Weight 258.317
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHOXZOLAMIDE

SMILES

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

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
Molecular Formula C9H10N2O3S2
Molecular Weight 258.317
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.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.

Originator

Approval Year

1957
118
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
CARDRASE

Approved Use

Ethoxzolamide is a carbonic anhydrase inhibitor used as diuretic and in glaucoma.
Primary
Approved
8583
CARDRASE

Approved Use

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

T1/2

ValueDoseCo-administeredAnalytePopulation
300 min
REVIEW
https://journals.physiology.org/doi/abs/10.1152/physrev.1967.47.4.595
, oral
 ETHOXZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
11%
OTHER
https://go.drugbank.com/drugs/DB00311
unknown, unknown
 ETHOXZOLAMIDE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
4%
REVIEW
https://journals.physiology.org/doi/abs/10.1152/physrev.1967.47.4.595
, 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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13817990
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13817990
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:
https://pubmed.ncbi.nlm.nih.gov/13817990
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13520609
unhealthy, 48 - 73
Health Status: unhealthy
Age Group: 48 - 73
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13520609
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:
https://pubmed.ncbi.nlm.nih.gov/13817990
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13817990
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:
https://pubmed.ncbi.nlm.nih.gov/13817990
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13817990
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:
https://pubmed.ncbi.nlm.nih.gov/13817990
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13817990
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
725
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BK channel
4
 yes [EC50 5.8 uM]
OAT1
730
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:101096
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:101096
eMolecules
498393
https://www.emolecules.com/cgi-bin/more?vid=498393
MolPort
MolPort-003-666-681
https://www.molport.com/shop/molecule-link/MolPort-003-666-681
ZINC
ZINC000000056721
http://zinc15.docking.org/substances/ZINC000000056721
PubMed

PubMed

TitleDatePubMed
T tubules and surface membranes provide equally effective pathways of carbonic anhydrase-facilitated lactic acid transport in skeletal muscle.
2010-12-13
Increased expression of carbonic anhydrase I in the synovium of patients with ankylosing spondylitis.
2010-12-08
Sharpey-Schafer lecture: gas channels.
2010-12
Role of carbonic anhydrase IV in the bicarbonate-mediated activation of murine and human sperm.
2010-11-24
Carbonic anhydrase II regulates differentiation of ameloblasts via intracellular pH-dependent JNK signaling pathway.
2010-11
Ocular inserts - Advancement in therapy of eye diseases.
2010-07
Alterations in osteoclast function and phenotype induced by different inhibitors of bone resorption--implications for osteoclast quality.
2010-06-01
Differences in transcription between free-living and CO2-activated third-stage larvae of Haemonchus contortus.
2010-04-27
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.
2010-04-15
Cyclodextrins in delivery systems: Applications.
2010-04
Nonenzymatic augmentation of lactate transport via monocarboxylate transporter isoform 4 by carbonic anhydrase II.
2010-04
Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis.
2010-03-11
Saccharomyces cerevisiae β-carbonic anhydrase: inhibition and activation studies.
2010
Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c.
2009-12-01
A pea mutant (costata) expressing higher activity in thylakoid membrane-bound carbonic anhydrase alters PSII downregulation mechanisms.
2009-08
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides.
2009-07-15
Titration calorimetry standards and the precision of isothermal titration calorimetry data.
2009-06-18
Measurement of nanomolar dissociation constants by titration calorimetry and thermal shift assay - radicicol binding to Hsp90 and ethoxzolamide binding to CAII.
2009-06-10
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis.
2009-05-14
Manganese-dependent carboanhydrase activity of photosystem II proteins.
2009-05
Label-free determination of protein-ligand binding constants using mass spectrometry and validation using surface plasmon resonance and isothermal titration calorimetry.
2009-04-18
QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software.
2009-04
Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties.
2009-02-17
Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates.
2009-02-01
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.
2009-02-01
The bicarbonate transporter is essential for Bacillus anthracis lethality.
2008-11
Lack of aquaporin-4 water transport inhibition by antiepileptics and arylsulfonamides.
2008-08-01
Isolation and characterization of a gene encoding carbonic anhydrase from Ostertagia ostertagi and quantitative measurement of expression during in vivo exsheathment.
2008-06-14
Antagonistic effect of juvenile hormone on hemocyte-spreading behavior of Spodoptera exigua in response to an insect cytokine and its putative membrane action.
2008-06
Diversity of inorganic carbon acquisition mechanisms by intact microbial mats of Microcoleus chthonoplastes (Cyanobacteriae, Oscillatoriaceae).
2008-05
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.
2008-04-15
Fluid and osmolyte recovery in the common pond snail Lymnaea stagnalis following full-body withdrawal.
2008-02
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.
2008
The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets.
2008
Direct non-cyclooxygenase-2 targets of celecoxib and their potential relevance for cancer therapy.
2007-12-03
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.
2007-12-01
Acclimation of wild-type cells and CO2-insensitive mutants of the green alga Chlorella ellipsoidea to elevated [CO2].
2007-08
Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors.
2007-07-01
Electrical parameters and ion species for active transport in human esophageal stratified squamous epithelium and Barrett's specialized columnar epithelium.
2007-07
Carbonic anhydrase II increases the activity of the human electrogenic Na+/HCO3- cotransporter.
2007-05-04
Inhibition of hypoxia-induced calcium responses in pulmonary arterial smooth muscle by acetazolamide is independent of carbonic anhydrase inhibition.
2007-04
Carbonic anhydrase inhibition prevents and reverts cardiomyocyte hypertrophy.
2007-02-15
Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors.
2007-01-25
Multiple sources of carbonic anhydrase activity in pea thylakoids: soluble and membrane-bound forms.
2007-01
Pulmonary vasodilation by acetazolamide during hypoxia is unrelated to carbonic anhydrase inhibition.
2007-01
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents.
2007
Pea leaf thylakoids contain several carbonic anhydrases.
2006-08-18
Expression, purification, kinetic, and structural characterization of an alpha-class carbonic anhydrase from Aedes aegypti (AaCA1).
2006-08
Evidence for a plasmalemma-based CO2 concentrating mechanism in Laminaria saccharina.
2006-06
Heterogeneous origin of carbonic anhydrase activity of thylakoid membranes.
2006-05
Patents

Patents

04416890
31
05059613
1
08354092
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:29 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:29 GMT 2025
Record UNII
Z52H4811WX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARDRASE
Preferred Name English
ETHOXZOLAMIDE
HSDB   MI   ORANGE BOOK   USP-RS   WHO-DD  
Common Name English
ETHOXZOLAMIDE [ORANGE BOOK]
Common Name English
Ethoxzolamide [WHO-DD]
Common 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
Classification Tree Code System Code
NCI_THESAURUS C29577
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
NCI_THESAURUS C448
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
Code System Code Type Description
PUBCHEM
3295
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
SMS_ID
100000078989
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023021
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
ChEMBL
CHEMBL18
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
MERCK INDEX
m5079
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB00311
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
EVMPD
SUB13739MIG
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
WIKIPEDIA
ETHOXZOLAMIDE
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
HSDB
3268
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
FDA UNII
Z52H4811WX
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
IUPHAR
6814
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
CAS
452-35-7
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
MESH
D005016
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
NCI_THESAURUS
C65561
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-199-5
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
DRUG CENTRAL
1089
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
CHEBI
101096
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
NSC
10679
Created by admin on Mon Mar 31 17:49:29 GMT 2025 , Edited by admin on Mon Mar 31 17:49:29 GMT 2025
PRIMARY
Related Record Type Details
CARBONIC ANHYDRASE 7
TARGET -> INHIBITOR
CARBONIC ANHYDRASE 1
TARGET -> INHIBITOR
CARBONIC ANHYDRASE 2
TARGET -> INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CARBONIC ANHYDRASE 4
TARGET -> INHIBITOR
Related Record Type Details
Structure of ETHOXZOLAMIDE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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