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:: 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.

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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.499
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: Page: p.149/433
unhealthy
n = 18
Health Status: unhealthy
Condition: Chronic simple glaucoma
Sex: M+F
Population Size: 18
Sources: Page: p.149/433
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: Page: p.149/433
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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.499
unhealthy, 48 - 73
n = 13
Health Status: unhealthy
Condition: Heart failure
Age Group: 48 - 73
Sex: M+F
Population Size: 13
Sources: Page: p.499
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: Page: p.149/433
unhealthy
n = 18
Health Status: unhealthy
Condition: Chronic simple glaucoma
Sex: M+F
Population Size: 18
Sources: Page: p.149/433
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: Page: p.149/433
unhealthy
n = 18
Health Status: unhealthy
Condition: Chronic simple glaucoma
Sex: M+F
Population Size: 18
Sources: Page: p.149/433
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: Page: p.149/433
unhealthy
n = 18
Health Status: unhealthy
Condition: Chronic simple glaucoma
Sex: M+F
Population Size: 18
Sources: Page: p.149/433
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
Spinal carbonic anhydrase contributes to nociceptive reflex enhancement by midazolam, pentobarbital, and propofol.
2003 Apr
Inorganic carbon limitation induces transcripts encoding components of the CO(2)-concentrating mechanism in Synechococcus sp. PCC7942 through a redox-independent pathway.
2003 Dec
Sodium and chloride transport in soft water and hard water acclimated zebrafish (Danio rerio).
2003 Dec 30
Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives.
2003 May 22
Bicarbonate-dependent depolarizing potentials in pyramidal cells and interneurons during epileptiform activity.
2003 Sep
Carbonic anhydrase isoform expression and functional role in rodent extraocular muscle.
2004 Aug
pH microdomains in oligodendrocytes.
2004 Aug 27
Carbonic anhydrase inhibitors. Inhibition of the prokariotic beta and gamma-class enzymes from Archaea with sulfonamides.
2004 Dec 20
Pdcd4 inhibits growth of tumor cells by suppression of carbonic anhydrase type II.
2004 Feb 12
Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor.
2004 Jun
Inhibition of alpha(1E) Ca(2+) channels by carbonic anhydrase inhibitors.
2004 Jun
Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides.
2004 Jun 21
Inhibition of 3T3-L1 adipocyte differentiation by 6-ethoxyzolamide: repressed peroxisome proliferator-activated receptor gamma mRNA and enhanced CCAAT/enhancer binding protein beta mRNA levels.
2004 May 1
Photosystem II associated carbonic anhydrase activity in higher plants is situated in core complex.
2004 Nov 5
Roles of carbonic anhydrase in photosynthesis of Skeletonema costatum.
2004 Oct
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides.
2004 Oct 15
HCO3- secretion in the esophageal submucosal glands.
2005 Apr
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
Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides.
2005 Feb 15
Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides.
2005 Feb 15
Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs?
2005 Feb 15
Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies.
2005 May 2
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
Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori.
2006 Apr 15
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
Evidence for a plasmalemma-based CO2 concentrating mechanism in Laminaria saccharina.
2006 Jun
Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs.
2006 Mar 23
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.
2007 Dec 1
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.
2008
Fluid and osmolyte recovery in the common pond snail Lymnaea stagnalis following full-body withdrawal.
2008 Feb
Diversity of inorganic carbon acquisition mechanisms by intact microbial mats of Microcoleus chthonoplastes (Cyanobacteriae, Oscillatoriaceae).
2008 May
Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates.
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. 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
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