Completing data — refresh the page later to see the latest
Basic information
- CAS
452-35-7- Standard SMILES
CCOc1ccc2nc(S(N)(=O)=O)sc2c1- InChIKey
OUZWUKMCLIBBOG-UHFFFAOYSA-N- Molecular formula
- C9H10N2O3S2
- Average molar mass
- 258.3 g/mol
- Monoisotopic mass
- 258.01328418
Overview
Ethoxzolamide is 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. It has a role as an EC 4.2.1.1 (carbonic anhydrase) inhibitor, a diuretic and an antiglaucoma drug. It is a sulfonamide, an aromatic ether and a member of benzothiazoles.
Names & identifiers
- Preferred name
- Ethoxzolamide
- IUPAC
- 6-ethoxy-1,3-benzothiazole-2-sulfonamide
- English name
- 6-Ethoxy-2-benzothiazolesulfonamide
- Molecular formula
- C9H10N2O3S2
- Molecular weight
- 258.32
Names & synonyms
ethoxzolamide452-35-76-Ethoxy-2-benzothiazolesulfonamideEthoxyzolamideEthoxazolamideEthamideCardrase6-Ethoxy-1,3-benzothiazole-2-sulfonamideEtoxzolamideGlaucotensilDiuretic CMingoral
Show more names
PNU-4191L-643786diureticcRedupresin
2-Benzothiazolesulfonamide, 6-ethoxy-DTXSID1023021U-4191NSC-10679Z52H4811WXDTXCID303021CHEBI:101096NSC10679
Database identifiers
- CAS
452-35-7- PubChem CID
- 3295
- DTXSID
DTXSID1023021- ChEMBL
CHEMBL18- ChEBI
CHEBI:101096- UNII
- Z52H4811WX
- EC Number
- 207-199-5
- Nikkaji
- J5.754A
Properties
Computed structural propertiesFilling in
- XLogP
- 2
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 341
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
LogP
log Kow = 2.01
0.4
OdorODORLESS
Color/Form
CRYSTALS FROM ETHYL ACETATE + SKELLYSOLVE B
WHITE OR SLIGHTLY YELLOW CRYSTALLINE POWDER
Solubility
SLIGHTLY SOL IN ALC, ACETONE, CHLOROFORM & ETHER; PRACTICALLY INSOL IN WATER
Water solubility = 40 mg/l @ 25 deg
6.88e-01 g/L
>38.7 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
188-190.5
188-190.5 °C
189 °C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Interactions
PATIENTS RECEIVING DIGITALIS GLYCOSIDES, HYPOKALEMIA MAY PREDISPOSE PATIENT TO DIGITALIS TOXICITY & POSSIBLY FATAL CARDIAC ARRHYTHMIAS MAY RESULT... DIURETICS, CORTICOSTEROIDS, CORTICOTROPIN & AMPHOTERICIN B /USED CONCOMITANTLY WITH CARBONIC ANHYDRASE INHIBITORS MAY CAUSE SEVERE HYPOKALEMIA/
CARBONIC ANHYDRASE INHIBITORS MAY AUGMENT EFFECTS OF OTHER DIURETICS SUCH AS THIAZIDES.../USEFUL/ IN ENHANCING & RESTORING RESPONSIVENESS TO MERCURIAL DIURETICS...RARELY, /DRUG/ MAY INTERFERE WITH HYPOGLYCEMIC RESPONSE TO INSULIN OR ORAL HYPOGLYCEMIC DRUGS, POSSIBLY BY CAUSING HYPOKALEMIA.
Chemistry & industry
Pharmacology
Protein Binding~89%
Pharmacodynamics
Ethoxzolamide is an inhibitor of the carbonic anhydrase enzyme in proximal renal tubules that works by decreasing the reabsorption of water, sodium, potassium, bicarbonate. It also decreases the activity of carbonic anhydrase expressed in the CNS, which leads to increased seizure threshold. Inhibition of carbonic anhydrase in the eye contributes to its effect of reducing intraocular pressure and decreasing aqueous humor.
Mechanism of Action
Ethoxzolamide binds to and inhibits carbonic anhydrase I, which plays an essential role in facilitating the transport of CO2 and H+ in the intracellular space, across biological membranes, and in the layers of the extracellular space. Through inhibition of the enzyme, the balance of applicable membrane equilibrium systems are affected.
MAJOR PHARMACOLOGICAL ACTION...IS INHIBITION OF...CARBONIC ANHYDRASE. STUDIES WITH PURIFIED ENZYME HAVE SHOWN THAT INHIBITION IS NONCOMPETITIVE. NONCATALYZED HYDRATION OR DEHYDRATION REACTION CAN TAKE PLACE, OF COURSE, IN ABSENCE OF ENZYME.
CARBONIC ANHYDRASE INHIBITORS...DECR CONCN OF HYDROGEN IONS AVAIL FOR EXCHANGE WITH SODIUM & POTASSIUM & TO COMBINE WITH BICARBONATE TO FORM CARBONIC ACID. /CARBONIC ANHYDRASE INHIBITORS/
...EFFECT /OF CARBONIC ANHYDRASE INHIBITORS/ ON INTRAOCULAR PRESSURE DOES NOT DEPEND UPON DIURESIS. THEY REDUCE AQUEOUS PRODN ... & THUS LOWER PRESSURE. /CARBONIC ANHYDRASE INHIBITORS/
Biological Half-Life2.5-5.5 hours
MeSH Pharmacological Classification
A class of compounds that reduces the secretion of H+ ions by the proximal kidney tubule through inhibition of CARBONIC ANHYDRASES.
Agents that promote the excretion of urine through their effects on kidney function.
Absorption, Distribution and Excretion
Rapidly absorbed with 65% bioavailability
ABSORBED FROM GI TRACT...DISTRIBUTED IN PLASMA, MUSCLES, BRAIN, KIDNEYS, LIVER, LUNGS, ERYTHROCYTES, AQUEOUS HUMOR, & CSF. APPROX 40%...EXCRETED UNCHANGED BY KIDNEYS /HUMAN, ORAL/
Related reactions
18 records
Compound notes
Loading…