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6-Ethoxybenzothiazol-2-sulfonamid

Ethoxzolamide

HCID 3295
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Grundinformationen

CAS
452-35-7
Standard-SMILES
CCOc1ccc2nc(S(N)(=O)=O)sc2c1
InChIKey
OUZWUKMCLIBBOG-UHFFFAOYSA-N
Summenformel
C9H10N2O3S2
Durchschnittliche Molmasse
258,3 g/mol
Monoisotopische Masse
258,01328418

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Ethoxzolamide
IUPAC
6-ethoxy-1,3-benzothiazole-2-sulfonamide
Lokaler Name
6-Ethoxybenzothiazol-2-sulfonamid
Englischer Name
6-Ethoxy-2-benzothiazolesulfonamide
Summenformel
C9H10N2O3S2
Molmasse
258.32

Namen und Synonyme

ethoxzolamide452-35-76-Ethoxy-2-benzothiazolesulfonamideEthoxyzolamideEthoxazolamideEthamideCardrase6-Ethoxy-1,3-benzothiazole-2-sulfonamideEtoxzolamideGlaucotensilDiuretic CMingoral
Weitere Namen anzeigen
PNU-4191L-643786diureticcRedupresin
2-Benzothiazolesulfonamide, 6-ethoxy-DTXSID1023021U-4191NSC-10679Z52H4811WXDTXCID303021CHEBI:101096NSC10679

Datenbank-Bezeichner

CAS
452-35-7
PubChem CID
3295
DTXSID
DTXSID1023021
ChEMBL
CHEMBL18
ChEBI
CHEBI:101096
UNII
Z52H4811WX
EC Number
207-199-5
Nikkaji
J5.754A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2
Polarare Oberfläche (TPSA)
119 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
3
Schwere Atome
16
Formalladung
0
Komplexität
341

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
LogP · 2 Einträge

log Kow = 2.01

0.4

OdorODORLESS
Color/Form · 2 Einträge

CRYSTALS FROM ETHYL ACETATE + SKELLYSOLVE B

WHITE OR SLIGHTLY YELLOW CRYSTALLINE POWDER

Solubility · 4 Einträge

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 · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 3 Einträge

188-190.5

188-190.5 °C

189 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Interactions · 4 Einträge

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.

Chemie und Industrie

Pharmakologische Informationen

Protein Binding~89%
Pharmacodynamics · 1 Eintrag

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 · 4 Einträge

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 · 2 Einträge

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 · 2 Einträge

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/

Zugehörige Reaktionen

18
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 185654
HRID 185654als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 345775
HRID 345775als Produktuspto-grants-1991_10
Reaktionsgleichung von HRID 345776
HRID 345776als Eduktuspto-grants-1991_10
Reaktionsgleichung von HRID 615599
HRID 615599als Eduktuspto-grants-1985_02
Reaktionsgleichung von HRID 663019
HRID 663019als EduktTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
Reaktionsgleichung von HRID 1110376
HRID 1110376als Eduktuspto-grants-1990_12
Reaktionsgleichung von HRID 1170774
HRID 1170774als Eduktuspto-grants-2010_11
Reaktionsgleichung von HRID 1240325
HRID 1240325als EduktTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
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Physical Description
Solid
Collision Cross Section · 2 Einträge

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

164.52 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
190 · 190-193 °C(lit.)
Siedepunkt
464.9 · 464.9±37.0 °C(Predicted)
Dichte
1.4767 · 1.4767 (rough estimate)
Brechungsindex
1.68 · 1.6800 (estimate)
storage temp.
Refrigerator
Löslichkeit
DMSO (Slightly), Ethyl Acetate (Slightly)
pka
8.12 · pKa 8.12(H2O t=25.0) (Uncertain)
Aggregatzustand
Solid
Farbe
Off-White
Wasserlöslichkeit
10.33 mg/L · 10.33mg/L(25 ºC)
Merck
13 · 13,3790
InChI
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)
InChIKey
OUZWUKMCLIBBOG-UHFFFAOYSA-N
SMILES
S1C2=CC(OCC)=CC=C2N=C1S(N)(=O)=O

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.

Human Toxicity Excerpts · 3 Einträge

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/

Antidote and Emergency Treatment · 1 Eintrag

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/

Sicherheitsdaten

wgk
3
RTECS-Nr.
DL6390000
risk_code
36/37/38
hazard_code
Xi
safety_code
26
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
452-35-7(Hazardous Substances Data)
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Cellular LocationsCytoplasm

Verwendung und Herstellung

UsesMEDICATION
Formulations/Preparations(CARDRASE, ETHAMIDE) /Non US product/

Anwendungen

Verwendenalcohol dehydrogenase inhibitor, antidote

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Ammoniak, wasserfrei6-Ethoxy-2-mercaptobenzothiazolKaliumpermanganatNatriumhypochlorit

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Ergänzende Hinweise

DefinitionChEBI: 1,3-Benzothiazole substituted a sulfonamide and an ethoxy group at positions 2 and 6, respectively. A carbonic anhydrase inhibitor, it has been used in the treatment of glaucoma, and as a diuretic.