Acetazolamide

Not to be confused with acetohexamide or methazolamide.

Acetazolamide
Skeletal formula of acetazolamide
Ball-and-stick model of the acetazolamide molecule
Clinical data
Trade namesDiamox, Diacarb, others
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, intravenous
Drug classCarbonic anhydrase inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding70–90%[1]
MetabolismNone[1]
Elimination half-life2–4 hours[1]
ExcretionUrine (90%)[1]
Identifiers
  • N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.400 Edit this at Wikidata
Chemical and physical data
FormulaC4H6N4O3S2
Molar mass222.24 g·mol−1
3D model (JSmol)
Melting point258 to 259 °C (496 to 498 °F)
  • NS(=O)(=O)c1nnc(s1)NC(=O)C
  • 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) checkY
  • Key:BZKPWHYZMXOIDC-UHFFFAOYSA-N checkY
  (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.[2][3] 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.[4] It is taken by mouth or injection into a vein.[2] Acetazolamide is a first generation carbonic anhydrase inhibitor and it decreases the ocular fluid and osmolality in the eye to decrease intraocular pressure.[5][6]

Common side effects include numbness, ringing in the ears, loss of appetite, vomiting, and sleepiness.[2] It is not recommended in those with significant kidney problems, liver problems, or who are allergic to sulfonamides.[2][4] Acetazolamide is in the diuretic and carbonic anhydrase inhibitor families of medication.[2] It works by decreasing the formation of hydrogen ions and bicarbonate from carbon dioxide and water.[2]

Acetazolamide came into medical use in 1952.[7] It is on the World Health Organization's List of Essential Medicines.[8] Acetazolamide is available as a generic medication.[2]

  1. ^ a b c d "Diamox Sequels (acetazolamide) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 13 April 2014. Retrieved 10 April 2014.
  2. ^ a b c d e f g "Acetazolamide". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  3. ^ Smith SV, Friedman DI (September 2017). "The Idiopathic Intracranial Hypertension Treatment Trial: A Review of the Outcomes". Headache. 57 (8): 1303–1310. doi:10.1111/head.13144. PMID 28758206. S2CID 13909867.
  4. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 439. hdl:10665/44053. ISBN 9789241547659.
  5. ^ Scozzafava A, Supuran CT (2014). "Glaucoma and the Applications of Carbonic Anhydrase Inhibitors". Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications. Subcellular Biochemistry. Vol. 75. Springer. pp. 349–359. doi:10.1007/978-94-007-7359-2_17. ISBN 978-94-007-7358-5. PMID 24146387.
  6. ^ "Acetazolamide: mechanism of action". www.openanesthesia.org. Retrieved 10 May 2017.
  7. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 390. ISBN 9780471899792. Archived from the original on 28 December 2016.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.