53. Acetazolamide

Nomenclature

CAS number: 59-66-5
N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide; 5-acetamido-1,3,4-thiadiazole-2-sulfonamide; 2-acetylamino-1,3,4-thiadiazole-5-sulfonamide; 6063; Acetamox (Tobishi-Santen); Atenezol (Tsuruhara); Défiltran (Gallier); Diamox (Barr); Didoc (Sawai); Diuriwas (IFI); Donmox (Horita); Edemox (Wassermann); Fonurit (Chinoin); Glaupax (Erco).
C4H6N4O3S2; mol wt 222.25.
C 21.62%, H 2.72%, N 25.21%, O 21.60%, S 28.85%.

Description and references

Carbonic anhydrase inhibitor. Prepn: R. O. Roblin, J. W. Clapp, J. Am. Chem. Soc. 72, 4890 (1950) DOI; J. W. Clapp, R. O. Roblin, US 2554816 (1951 to Am. Cyanamid). HPLC determn in pharmaceuticals: Z. S. Gomaa, Biomed. Chromatogr. 7, 134 (1993) DOI PubMed. Effect on retinal circulation: S. M. B. Rassam et al., Eye 7, 697 (1993) PubMed. Clinical trial in postoperative elevation of intraocular pressure: I. D. Ladas et al., Br. J. Ophthalmol. 77, 136 (1993) DOI PubMed. Comprehensive description: J. Parasrampuria, Anal. Profiles Drug Subs. Excip. 22, 1-32 (1993) DOI. Review of efficacy in acute mountain sickness: L. D. Ried et al., J. Wilderness Med. 5, 34-48 (1994).

Chemical structure

Properties

Crystals from water, mp 258-259° (effervescence). Weak acid. pKa 7.2. Sparingly sol in practically boiling water. Slightly sol in alcohol, acetone. Very slightly sol in water. Practically insol in carbon tetrachloride, chloroform, ether. Soly (mg/ml): polyethylene glycol-400 87.81; propylene glycol 7.44; ethanol 3.93; glycerin 3.65; water 0.72.

Derivative

Sodium salt.

Nomenclature

CAS number: 1424-27-7
Vetamox (Am. Cyanamid).

Therapeutic Category

Antiglaucoma; diuretic; in treatment of acute mountain sickness.

Therapeutic Category (Veterinary)

Diuretic.

Keywords

Antiglaucoma; Carbonic Anhydrase Inhibitor; Diuretic; Sulfonamide Derivatives