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Ethoxzolamide

Ethoxzolamide structure

CAS No:
452-35-7
Formula:
C9H10N2O3S2
Chemical Name:
Ethoxzolamide
Synonyms:
2-Benzothiazolesulfonamide,6-ethoxy-;6-Ethoxy-2-benzothiazolesulfonamide;U 4191;Cardrase;Diuretic C;Ethoxyzolamide;Ethoxzolamide;Etoxzolamide;L 643786;PNU 4191;Glaucotensil;Ethamide;Redupresin;NSC 10679;6-Ethoxyzolamide
Categories:
Active Pharmaceutical Ingredients > Urinary System Drugs

Description

Ethoxzolamide is a carbonic anhydrase inhibitor with Ki of 1 nM.

Solid

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 member of benzothiazoles and a sulfonamide.|Ethoxzolamide is a sulfonamide used as diuretic and in glaucoma. It inhibits carbonic anhydrase activity in proximal renal tubules to decrease reabsorption of water, sodium, potassium, bicarbonate. Its pharmacological activity thus confers the risk for hypokalemia.|Ethoxzolamide is a sulfonamide and carbonic anhydrase (CA) inhibitor with diuretic and anti-glaucoma activity. In the eye, ethoxzolamide inhibits CA, thereby decreasing the secretion of aqueous humor. This may relieve intraocular pressure. Also, this agent prevents reabsorption of bicarbonate and sodium in the proximal convoluted tubule thereby producing a mild diuresis.|A carbonic anhydrase inhibitor used as diuretic and in glaucoma. It may cause hypokalemia.

Ethoxzolamide Basic Attributes

Molecular Weight：

258.32

Exact Mass：

258.32

EC Number：

207-199-5

UNII：

Z52H4811WX

NSC Number：

759129|10679

DSSTox ID：

DTXSID1023021

NCI Thesaurus Code：

C65561

Color/Form：

CRYSTALS FROM ETHYL ACETATE + SKELLYSOLVE B|WHITE OR SLIGHTLY YELLOW CRYSTALLINE POWDER

HScode：

2935009090

Characteristics

PSA：

119

XLogP3：

0.4

Appearance：

Solid

Density：

1.47g/cm3

Melting Point：

188-190.5 °C

Boiling Point：

464.9ºC at 760mmHg

Flash Point：

235ºC

Refractive Index：

1.644

Water Solubility：

10.33mg/L(25 ºC)

Odor：

ODORLESS

Collision Cross Section：

152.7 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

RTECS Number：

DL6390000

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

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.

Toxicity

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.|ALKALINIZATION OF URINE PRODUCED BY /DRUG INCREASES/ RATE OF EXCRETION OF WEAK ACIDS, INCLUDING PHENOBARBITAL & SALICYLATES...METHENAMINE, METHENAMINE HIPPURATE, & METHENAMINE MANDELATE...MAY BE INACTIVE IN ALKALINE URINE PRODUCED BY CARBONIC ANHYDRASE INHIBITORS.|CARBONIC ANHYDRASE INHIBITORS INCREASE EXCRETION OF LITHIUM...ALKALINIZATION OF URINE PRODUCED BY /DRUG/ MAY DECREASE RATE OF EXCRETION OF...AMPHETAMINES, PROCAINAMIDE, QUINIDINE...TRICYCLIC ANTIDEPRESSANTS & /THEIR EFFECTS/ MAY BE ENHANCED &/OR PROLONGED.

Protein Binding：

~89%

Drug Information

Drug Indication：

For use in the treatment of duodenal ulcers, as a diuretic, and in the treatment of glaucoma, and may also be useful in the treatment of seizures associated with epilepsy.

Therapeutic Uses：

Carbonic Anhydrase Inhibitors; Diuretics|.../USED FOR/ ADJUNCTIVE TREATMENT OF CHRONIC SIMPLE (OPEN-ANGLE) GLAUCOMA, SECONDARY GLAUCOMA, & PREOPERATIVELY IN ACUTE ANGLE-CLOSURE GLAUCOMA TO LOWER INTRAOCULAR PRESSURE PRIOR TO SURGERY.|EFFECTIVE DOSE APPEARS TO VARY FROM 125 TO 1000 MG/DAY, GIVEN ORALLY IN DIVIDED DOSES.|MEDICATION (VET): AS DIURETIC IN MILD CONGESTIVE CARDIAC EDEMAS.|For more Therapeutic Uses (Complete) data for ETHOXZOLAMIDE (6 total), please visit the HSDB record page.

Drug Warnings：

... CARBONIC ANHYDRASE INHIBITORS SHOULD BE USED CAUTIOUSLY IN PATIENTS WITH OBSTRUCTIVE PULMONARY DISEASE BECAUSE THEY MAY PRECIPITATE ACUTE RESP FAILURE. /CARBONIC ANHYDRASE INHIBITORS/|SINCE CARBONIC ANHYDRASE INHIBITORS MAY HAVE TERATOGENIC EFFECTS, THESE DRUGS SHOULD BE AVOIDED DURING EARLY PREGNANCY. /CARBONIC ANHYDRASE INHIBITORS/|CARBONIC ANHYDRASE INHIBITORS ALSO ARE ADMINISTERED FOR PREOPERATIVE TREATMENT OF ACUTE ANGLE-CLOSURE AND CONGENITAL GLAUCOMAS. ... mORE THAN 50% OF PATIENTS ... MUST DISCONTINUE THERAPY BECAUSE OF ADVERSE REACTIONS. ... OSMOTIC AGENTS ARE USED TO REDUCE INTRAOCULAR PRESSURE AND VITREOUS VOLUME RAPIDLY PRIOR TO IRIDECTOMY AND OTHER OCULAR SURGICAL PROCEDURES. /CARBONIC ANHYDRASE INHIBITORS/|RENAL COLIC, HEMATURIA & OLIGURIA OR ANURIA MAY OCCUR DURING PROLONGED THERAPY... CARBONIC ANHYDRASE INHIBITORS REDUCE URIC ACID EXCRETION & INCR BLOOD URIC ACID LEVEL. ... HYPERURICEMIA IS USUALLY ASYMPTOMATIC BUT RARELY HAS LED TO AN EXACERBATION OF GOUT. /CARBONIC ANHYDRASE INHIBITORS/|For more Drug Warnings (Complete) data for ETHOXZOLAMIDE (7 total), please visit the HSDB record page.

Pharmacology：

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.

MeSH：

A class of compounds that reduces the secretion of H+ ions by the proximal kidney tubule through inhibition of CARBONIC ANHYDRASES. (See all compounds classified as Carbonic Anhydrase Inhibitors.)|Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

Absorption：

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/

Biological Half-Life：

2.5-5.5 hours

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/

Antidote：

Carbonic anhydrase inhibitors ... enhance sodium excretion by reducing sodium bicarbonate reabsorption in the early proximal convoluted tubule. Passive sodium chloride reabsorption in the late proximal convoluted tubule is consequently decreased, ... potassium excretion is increased during initial therapy ... Clinically significant hypokalemia is seldom a problem, because excess hydrogen ions in the extracellular fluid tend to diffuse into the cells and displace potassium ions ... . After several days of continuous administration, a mild hyperchloremic acidosis develops, which decreases the diuretic effect. /Carbonic anhydrase inhibitors/

Human Toxicity Excerpts：

SERIOUS TOXIC REACTIONS ARE INFREQUENT. WITH LARGE DOSES, MANY PT EXHIBIT DROWSINESS & PARESTHESIAS. IN HEPATIC CIRRHOSIS, EPISODES OF DISORIENTATION MAY BE INDUCED. ... HYPERSENSITIVITY REACTIONS ARE RELATIVELY RARE. THEY CONSIST IN FEVER, SKIN REACTIONS, BONE MARROW DEPRESSION, & SULFONAMIDE-LIKE RENAL LESIONS.|CARBONIC ANHYDRASE INHIBITORS FREQUENTLY CAUSE ... ANOREXIA, WT LOSS, /GI DISTURBANCES (GASTRIC DISTRESS, NAUSEA, VOMITING, OR DIARRHEA)/, ... LETHARGY & DEPRESSION ARE COMMON & OFTEN UNRECOGNIZED UNTIL DRUG IS DISCONTINUED... /CARBONIC ANHYDRASE INHIBITORS/|...HEADACHE.../FATIGUE & DIZZINESS/ ALSO MAY OCCUR. ... TRANSIENT MYOPIA ... HAS BEEN REPORTED AND MAY RESULT FROM CHANGES IN LENS HYDRATION ... ./CARBONIC ANHYDRASE INHIBITORS/

MeSH Entry Terms：

Ethamide

Ethoxzolamide Use and Manufacturing

Uses

alcohol dehydrogenase inhibitor, antidote

Formulations：

(CARDRASE, ETHAMIDE) /Non US product/

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:258.3
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:258.01328453
Monoisotopic Mass:258.01328453
Topological Polar Surface Area:119
Heavy Atom Count:16
Complexity:341
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes