aspirin

Also known as acetylsalicylic acid, ASA, o-acetoxybenzoic acid, o-carboxyphenyl acetate, salicylic acid acetate, o-(acetyloxy)benzoic acid, 2-carboxyphenyl acetate, 2-acetoxybenzoic acid

Aspirin () is the genericized trademark for acetylsalicylic acid (ASA), a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and inflammation, and as an antithrombotic. Aspirin is used to treat inflammatory conditions including Kawasaki disease, pericarditis, and rheumatic fever.

OverviewAI-generated

Aspirin, also known as acetylsalicylic acid, is a chemical compound with the formula C₉H₈O₄. Its IUPAC name is 2-acetyloxybenzoic acid. The substance has a molecular mass of 180.042 or 180.16 depending on the source. It is recognized in the National Inventors Hall Of Fame collection.

Physically, aspirin has a density of 1.35 and a melting point of 275. It decomposes at 284. The vapor pressure is 0. Its solubility is 0.003. The pKa is 3.49. It has zero charge and one hydrogen bond donor. There are four hydrogen bond acceptors. The canonical SMILES is CC(=O)OC1=CC=CC=C1C(=O)O.

Safety data indicates a minimal lethal dose of 1216 and a median lethal dose (LD50) of 3500. The minimum explosive concentration is 40. Exposure limits include a time-weighted average of 5 and a short-term limit of 0.5. In literature, a PubMed query for aspirin yields 79,920 results. The subject is referenced by 1,859 other encyclopedia articles.

Synthesized by Vinony from 33 facts across 5 sources: Wikidata, PubChem, PubMed, Vinony collections, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.metabolism: Liver (CYP2C19 and possibly CYP3A), some is also hydrolysed to salicylate in the gut wall.
Drug.drug_name: Acetylsalicylic acid
Drug.INN: none
Drug.imageL: Aspirin-skeletal.svg
Drug.image_classL: skin-invert-image
Drug.imageR: Aspirin-B-3D-balls.png
Drug.image_classR: bg-transparent
Drug.image2: acetylsalicylic_acid.jpg
Drug.caption2: pure acetylsalicylic acid
Drug.tradename: Bayer Aspirin, others
Drug.MedlinePlus: a682878
Drug.DailyMedID: Acetylsalicylic acid
Drug.pregnancy_AU: C
Drug.routes_of_administration: Oral, rectal
Drug.class: Nonsteroidal anti-inflammatory drug (NSAID)
Drug.ATC_prefix: A01
Drug.legal_AU: S6
Drug.legal_AU_comment: /Schedule 5; Schedule 4; Schedule 2 Appendix F, clause 4

via Wikipedia infobox

Chemical data

Formula: C9H8O4
Molecular weight: 180.16 g/mol
IUPAC name: 2-acetyloxybenzoic acid
SMILES: CC(=O)OC1=CC=CC=C1C(=O)O
InChIKey: BSYNRYMUTXBXSQ-UHFFFAOYSA-N
XLogP: 1.2
Polar surface area: 63.6 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

79,920 papers

Low-dose aspirin for the prevention of atherosclerotic cardiovascular disease.ReviewEuropean heart journal · 2024Patrono CDOI: 10.1093/eurheartj/ehae324
Aspirin in Primary Prevention of Cardiovascular Events.ReviewClinical medicine & research · 2020Soodi D, VanWormer JJ, Rezkalla SHDOI: 10.3121/cmr.2020.1548
Aspirin in the Modern Era of Cardiovascular Disease Prevention.ReviewMethodist DeBakey cardiovascular journal · 2021Murphy E, Curneen JMG, McEvoy JWDOI: 10.14797/mdcvj.293
Use of aspirin to reduce risk of initial vascular events in patients at moderate risk of cardiovascular disease (ARRIVE): a randomised, double-blind, placebo-controlled trial.Lancet (London, England) · 2018Gaziano JM, Brotons C, Coppolecchia R et al.DOI: 10.1016/S0140-6736(18)31924-X
Aspirin nanosensors.ReviewClinica chimica acta; international journal of clinical chemistry · 2025Koohkansaadi G, Tabean M, Mohagheghi A et al.DOI: 10.1016/j.cca.2025.120222
Aspirin and its pleiotropic application.ReviewEuropean journal of pharmacology · 2020Hybiak J, Broniarek I, Kiryczyński G et al.DOI: 10.1016/j.ejphar.2019.172762
Aspirin in the Prevention of Colorectal Neoplasia.ReviewAnnual review of medicine · 2021Drew DA, Chan ATDOI: 10.1146/annurev-med-060319-120913
Aspirin is associated with improved outcomes in patients with sepsis-induced myocardial injury: An analysis of the MIMIC-IV database.Journal of clinical anesthesia · 2024Dong Y, Wei S, Liu Y et al.DOI: 10.1016/j.jclinane.2024.111597

via PubMed

Wikidata facts

Has part: hydrogen
Named after: Filipendula ulmaria
Mass: 180.042
Image: Aspirin.jpg
Has use: essential medicine

Show 30 more facts

has characteristic: bitterness
minimum explosive concentration: 40
Commons category: Acetylsalicylic acid
chemical formula: C₉H₈O₄
minimal lethal dose: 1216
route of administration: oral administration
topic's main category: Category:Aspirin
found in taxon: liquorice
density: 1.35
NIOSH Pocket Guide ID: 0010
melting point: 138
decomposition point: 284
vapor pressure: 0
solubility: 0.003
time-weighted average exposure limit: 5
World Health Organisation international non-proprietary name: acetylsalicylic acid
median lethal dose (LD50): 1020
short-term exposure limit: 0.5
medical condition treated: myocardial infarction
canonical SMILES: CC(=O)OC1=CC=CC=C1C(=O)O
significant drug interaction: acetazolamide
discoverer or inventor: Felix Hoffmann
subject has role: analgesic
may prevent disease: myocardial infarction
physically interacts with: Prostaglandin-endoperoxide synthase 1
WordLift URL: data.medicalrecords.com/medicalrecords/healthwise/aspirin_for_pain__fever__and_inflammation
history of topic: history of aspirin
hashtag: aspirin
native label: Acidum acetylsalicylicum
pKa: 3.49

Sources (10)

via Wikidata · CC0

~46 min read

Encyclopedic overview

39 sections

Contents

Brand vs. generic name
Chemical properties
Synthesis
Physical properties
Polymorphism
Mechanism of action
Discovery of the mechanism
Prostaglandins and thromboxanes
COX-1 and COX-2 inhibition
Additional mechanisms
Formulations
Pharmacokinetics
History
Trademark
Compendial status
Medical use
Pain
Fever
Inflammation
Heart attacks and strokes
Cancer prevention
Psychiatry
Other uses
Resistance
Dosages
Adverse effects
Contraindications
Gastrointestinal
Retinal vein occlusion
Central effects
Reye syndrome
Skin
Other adverse effects
Overdose
Interactions
Research
Veterinary medicine
References
Further reading

Aspirin is also used long-term to help prevent further heart attacks, ischaemic strokes, and blood clots in people at high risk. For pain or fever, effects typically begin within 30 minutes. Aspirin works similarly to other NSAIDs but also suppresses the normal functioning of platelets.

Excerpted from Wikipedia’s “aspirin” article, available under the CC BY-SA 4.0 licence.