Acetazolamide

Acetazolamide
Clinical data
Trade names	Diamox, Diacarb, others
AHFS/Drugs.com	Monograph
Pregnancy; category	AU: B3;
Routes of; administration	By mouth, intravenous
Drug class	Carbonic anhydrase inhibitor
ATC code	S01EC01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Protein binding	70–90%
Metabolism	None
Elimination half-life	2–4 hours
Excretion	Urine (90%)
Identifiers
	IUPAC name N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide;
CAS Number	59-66-5 ;
PubChem CID	1986;
IUPHAR/BPS	6792;
DrugBank	DB00819 ;
ChemSpider	1909 ;
UNII	O3FX965V0I;
KEGG	D00218 ;
ChEBI	CHEBI:27690 ;
ChEMBL	ChEMBL20 ;
PDB ligand	AZM (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID7022544 ;
ECHA InfoCard	100.000.400
Chemical and physical data
Formula	C4H6N4O3S2
Molar mass	222.24 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	258 to 259 °C (496 to 498 °F)
	SMILES NS(=O)(=O)c1nnc(s1)NC(=O)C;
	InChI InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9) ; Key:BZKPWHYZMXOIDC-UHFFFAOYSA-N ;
	(verify)

Acetazolamide, sold under the trade name Diamox among others, is a medication used to treat glaucoma, epilepsy, acute mountain sickness, periodic paralysis, idiopathic intracranial hypertension (raised brain pressure of unclear cause), heart failure and to alkalinize urine. It may be used long term for the treatment of open angle glaucoma and short term for acute angle closure glaucoma until surgery can be carried out. It is taken by mouth or injection into a vein. Acetazolamide is a first generation carbonic anhydrase inhibitor and it decreases the ocular fluid and osmolality in the eye to decrease intraocular pressure.

Common side effects include numbness, ringing in the ears, loss of appetite, vomiting, and sleepiness. It is not recommended in those with significant kidney problems, liver problems, or who are allergic to sulfonamides. Acetazolamide is in the diuretic and carbonic anhydrase inhibitor families of medication. It works by decreasing the formation of hydrogen ions and bicarbonate from carbon dioxide and water.

Acetazolamide came into medical use in 1952. It is on the World Health Organization's List of Essential Medicines. Acetazolamide is available as a generic medication.

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