5962. Methazolamide

Nomenclature

CAS number: 554-57-4
N-[5-(Aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide; N-(4-methyl-2-sulfamoyl-Δ2-1,3,4-thiadiazolin-5-ylidene)acetamide; 5-acetylamino-4-methyl-Δ2-1,3,4-thiadiazoline-2-sulfonamide.
C5H8N4O3S2; mol wt 236.27.
C 25.42%, H 3.41%, N 23.71%, O 20.31%, S 27.14%.

Description and references

Carbonic anhydrase inhibitor. Prepn: Young et al., J. Am. Chem. Soc. 78, 4649 (1956); US 2783241 (1957 to Am. Cyanamid); Pala, Farmaco Ed. Sci. 13, 650 (1958). HPLC determn in biological fluids: G. R. Iyer, D. R. Taft, J. Pharm. Biomed. Anal. 16, 1021 (1998). Effects on intraocular pressure and aqueous humor flow rate in dogs: B. J. Skorobohach et al., Am. J. Vet. Res. 64, 183 (2003).

Chemical structure

Properties

Crystals from water, mp 213-214°. pKa 7.30. uv max (95% ethanol): 254 nm (log ε 3.66); (0.1N NaOH): 247 nm (log ε 3.61). Sol in DMF; slightly sol in acetone; very slightly sol in water, alcohol.

Therapeutic Category

Diuretic; antiglaucoma.

Therapeutic Category (Veterinary)

Antiglaucoma.

Keywords

Antiglaucoma; Carbonic Anhydrase Inhibitor; Diuretic; Sulfonamide Derivatives