Acetazolamide

Acetazolamide
Clinical data


Trade names	Diamox, Diacarb, others
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	by mouth or intravenous
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
Biological 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^Y
PubChem (CID)	1986
IUPHAR/BPS	6792
DrugBank	DB00819^Y
ChemSpider	1909^Y
UNII	O3FX965V0I^Y
KEGG	D00218^Y
ChEBI	CHEBI:27690^Y
ChEMBL	CHEMBL20^Y
PDB ligand ID	AZM (PDBe, RCSB PDB)
ECHA InfoCard	100.000.400
Chemical and physical data
Formula	C₄H₆N₄O₃S₂
Molar mass	222.245 g/mol
3D model (Jmol)	Interactive image
Melting point	258 to 259 °C (496 to 498 °F)
SMILES O=S(=O)(c1nnc(s1)NC(=O)C)N
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)^Y Key:BZKPWHYZMXOIDC-UHFFFAOYSA-N^Y

Acetazolamide, sold under the trade name Diamox among others, is a medication used to treat glaucoma, epilepsy, altitude sickness, periodic paralysis, and heart failure. 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.

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 amount of hydrogen ions and bicarbonate in the body.

Acetazolamide came into medical use in 1952. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Acetazolamide is available as a generic medication. The wholesale cost in the developing world is about 1.40 to 16.93 USD per month. In the United States the wholesale cost is about 125.34 USD per month.