Structure via PubChem · Public domain (PubChem)
acetazolamide
Sign in to saveAlso known as Diamox®, N-[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide, Diamox, Acetazolamide 250mg, 5-acetamido-1,3,4-thiadiazole-2-sulfonamide, 5-acetylamino-1,3,4-thiadiazole-2-sulfonamide, Acetazolamid, Acetazolamida
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 de
OverviewAI-generated
Acetazolamide is a chemical compound with the formula C₄H₆N₄O₃S₂. Its IUPAC name is N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide, and it is also stylized as acetaZOLAMIDE. The substance has a mass of 221.988 and a weight of 222.3. It possesses a charge of 0, with an xlogp of -0.3 and a topological polar surface area of 152.
The molecule contains two hydrogen bond donors and seven hydrogen bond acceptors. Its canonical SMILES notation is CC(=O)NC1=NN=C(S1)S(=O)(=O)N. The compound is associated with a price of 0.1881.
Acetazolamide is the subject of 10,750 entries in PubMed literature. It is referenced by 340 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C4H6N4O3S2
- Molecular weight
- 222.3 g/mol
- IUPAC name
- N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
- SMILES
- CC(=O)NC1=NN=C(S1)S(=O)(=O)N
- InChIKey
- BZKPWHYZMXOIDC-UHFFFAOYSA-N
- XLogP
- -0.3
- Polar surface area
- 152 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1953
- Admin. routes
- oral, parenteral
- Indications
- kidney disease, Cardiodysrhythmic potassium-sensitive periodic paralysis, altitude sickness, heart failure
via ChEMBL · EBI
Research
10,750 papers- Acetazolamide use in postoperative CSF leak prevention: A literature review.American journal of otolaryngology · 2025
- Acetazolamide in the treatment of seizures.The Annals of pharmacotherapy · 1996
- Evaluating off-label uses of acetazolamide.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 2018
- [Acetazolamide].Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke · 1990
- Acetazolamide: a forgotten diuretic agent.Cardiology in review · 2011
via PubMed
Wikidata facts
- Subclass of
- sulfonamide
- Mass
- 221.988
- Has use
- medication
Show 8 more facts
- Commons category
- Acetazolamide
- chemical formula
- C₄H₆N₄O₃S₂
- significant drug interaction
- lithium
- medical condition treated
- altitude sickness
- price
- 0.0262
- canonical SMILES
- CC(=O)NC1=NN=C(S1)S(=O)(=O)N
- route of administration
- oral administration
- stylized name
- acetaZOLAMIDE
Sources (7)
via Wikidata · CC0
~12 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- High altitude sickness
- Pregnancy and lactation
- Side effects
- Contraindications
- Interactions
- Mechanism of action
- History
- Research
- Veterinary use
- References
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.
Excerpted from Wikipedia’s “acetazolamide” article, available under the CC BY-SA 4.0 licence.