6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Property

Melting point:

190-193 °C(lit.)

Boiling point:

464.9±37.0 °C(Predicted)

Density 

1.4767 (rough estimate)

refractive index 

1.6800 (estimate)

storage temp. 

Refrigerator

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly)

pka

pKa 8.12(H2O t=25.0) (Uncertain)

form 

Solid

color 

Off-White

Water Solubility 

10.33mg/L(25 ºC)

Merck 

13,3790

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

DL6390000

Hazardous Substances Data

452-35-7(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Chemical Properties,Usage,Production

Originator

Cardrase,Upjohn,US,1957

Uses

alcohol dehydrogenase inhibitor, antidote

Uses

Ethoxzolamide is used in the treatment of glaucoma, and is also used as a diuretic, acting as a carbonic anhydrase inhibitor.

Definition

ChEBI: 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.

Manufacturing Process

Preparation of 6-Ethoxybenzothiazole-2-Sulfenamide: A solution prepared by dissolving 21.0 grams (0.1 mol) of 6-ethoxybenzothiazole-2-thiol, Sebrell and Boord, J. Am. Chem. Soc. 45: 2390 to 2399 (1923), in 75 ml of water containing 5 grams of sodium hydroxide, and 75 ml of 10% sodium hypochlorite solution were added simultaneously to 300 ml of concentrated ammonium hydroxide which was cooled to 0°C, and vigorously stirred. During the addition the temperature was not allowed to rise above 5°C. The resulting solid was recovered by filtration, washed thoroughly with water, and dried at room temperature under reduced pressure. There was obtained 21 grams of 6-ethoxybenzothiazole-2-sulfenamide melting at 132° to 155°C (decomposition). Recrystallization from ethyl acetate gave a product melting at 140.5° to 143°C (decomposition).
Preparation of 6-Ethoxybenzothiazole-2-Sulfonamide: A solution of 3.39 grams (0.015 mol) of the sulfenamide in 100 ml of acetone was treated dropwise, with stirring, with a solution of 3.5 grams of potassium permanganate in 100 ml of water. The temperature rose to 42°C. After stirring an additional 10 minutes the reaction mixture was filtered to remove manganese dioxide, the latter was washed with 100 ml of warm water, and the combined filtrates were concentrated under reduced pressure to remove acetone. The residual solution was treated with charcoal, filtered and acidified with concentrated hydrochloric acid. After standing in the refrigerator for 4 hours the solid sulfonamide was recovered by filtration, washed with water and dried. There was obtained 2.37 grams of 6-ethoxybenzothiazole-2-sulfonamide melting at 180° to 190°C. Recrystallization from ethyl acetate-Skellysolve B gave 1.25 grams of material melting at 188° to 190.5°C.

Therapeutic Function

Diuretic, Cardiotonic, Smooth muscle relaxant, Respiratory stimulant

General Description

6-Ethoxy-2-benzothiazolesulfonamide is a membrane permeable carbonic anhydrase inhibitor and its ocular disposition and pharmacology in normal albino rabbits has been investigated. It causes inhibition of insulin degradation in vitro.

Clinical Use

Ethoxzolamide is another carbonic anhydrase inhibitor with properties and uses resembling those of acetazolamide.