Ethoxzolamide

Ethoxzolamide (alternatively known as ethoxyzolamide) is a sulfonamide medication that functions as a carbonic anhydrase inhibitor. It is used in the treatment of glaucoma and duodenal ulcers, and as a diuretic. It may also be used in the treatment of some forms of epilepsy.

Ethoxzolamide

Clinical data
ATC code	None
Pharmacokinetic data
Protein binding	~89%
Elimination half-life	2.5–5.5 hours
Identifiers
IUPAC name 6-Ethoxy-1,3-benzothiazole-2-sulfonamide
CAS Number	452-35-7^Y
PubChem CID	3295
IUPHAR/BPS	6814
DrugBank	DB00311^Y
ChemSpider	3179^Y
UNII	Z52H4811WX
KEGG	D02441^Y
ChEBI	CHEBI:101096^Y
ChEMBL	ChEMBL18^Y
CompTox Dashboard (EPA)	DTXSID1023021
ECHA InfoCard	100.006.546
Chemical and physical data
Formula	C9H10N2O3S2
Molar mass	258.31 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=S(=O)(c1nc2ccc(OCC)cc2s1)N
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)^Y Key:OUZWUKMCLIBBOG-UHFFFAOYSA-N^Y
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Pharmacology

Ethoxzolamide, a sulfonamide, inhibits carbonic anhydrase activity in proximal renal tubules to decrease reabsorption of water, sodium, potassium, bicarbonate. It also decreases carbonic anhydrase in the CNS, increasing the seizure threshold. This reduction in carbonic anhydrase also reduces the intraocular pressure in the eye by decreasing aqueous humor.

Mechanism of action

Ethoxzolamide binds and inhibits carbonic anhydrase I. Carbonic anhydrase plays an essential role in facilitating the transport of carbon dioxide and protons in the intracellular space, across biological membranes and in the layers of the extracellular space. The inhibition of this enzyme effects the balance of applicable membrane equilibrium systems.

Synthesis

Ethoxzolamide synthesis: GB 795174; J. Korman, U.S. Patent 2,868,800 (1958, 1959 both to Upjohn).

See also

• Dimazole
• Dithiazanine iodide