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INN: acetylsalicylic acid
Clinical data
Pronunciation acetylsalicylic acid /??si?t?l?s�l?'s?l?k/
Trade names Bayer Aspirin, many others
Other names 2-acetoxybenzoic acid
acetylsalicylic acid
O-acetylsalicylic acid, Aspirin (BAN UK), Aspirin (USAN US)
AHFS/ Monograph
MedlinePlus a682878
License data
US FDA: Aspirin
AU: C [1]
US: N (Not classified yet) [1]
Routes of
administration by mouth, rectal, lysine acetylsalicylate may be given
intravenously or intramuscularly
ATC code
A01AD05 (WHO) B01AC06 (WHO), N02BA01 (WHO)
Legal status
Legal status
AU: OTC except when given intravenously (in which case it is schedule 4), used in
animal medicine (schedule 5/6) or when the dose is higher than usual.
UK: General sales list (GSL, OTC)
Pharmacokinetic data
Bioavailability 80�100%[3]
Protein binding 80�90%[2]
Metabolism Liver, (CYP2C19 and possibly CYP3A), some is also hydrolysed to
salicylate in the gut wall.[2]
Elimination half-life Dose-dependent; 2 h to 3 h for low doses (100 mg or less),
15 h to 30 h for large doses.[2]
Excretion Urine (80�100%), sweat, saliva, feces[3]
IUPAC name[show]
CAS Number
50-78-2 ?
PubChem CID
DB00945 ?
2157 ?
D00109 ?
CHEBI:15365 ?
ChEMBL25 ?
PDB ligand
CompTox Dashboard (EPA)
DTXSID5020108 Edit this at Wikidata
ECHA InfoCard 100.000.059 Edit this at Wikidata
Chemical and physical data
Formula C9H8O4
Molar mass 180.158[4] g�mol-1
3D model (JSmol)
Interactive image
Density 1.40 g/cm3
Melting point 136 �C (277 �F) [4]
Boiling point 140 �C (284 �F) (decomposes)
Solubility in water 3 mg/mL (20 �C)
Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to treat
pain, fever, or inflammation.[5] Specific inflammatory conditions which aspirin is
used to treat include Kawasaki disease, pericarditis, and rheumatic fever.[5]
Aspirin given shortly after a heart attack decreases the risk of death.[5] Aspirin
is also used long-term to help prevent further heart attacks, ischaemic strokes,
and blood clots in people at high risk.[5] It may also decrease the risk of certain
types of cancer, particularly colorectal cancer.[6] For pain or fever, effects
typically begin within 30 minutes.[5] Aspirin is a nonsteroidal anti-inflammatory
drug (NSAID) and works similarly to other NSAIDs but also suppresses the normal
functioning of platelets.[5]

One common adverse effect is an upset stomach.[5] More significant side effects
include stomach ulcers, stomach bleeding, and worsening asthma.[5] Bleeding risk is
greater among those who are older, drink alcohol, take other NSAIDs, or are on
other blood thinners.[5] Aspirin is not recommended in the last part of pregnancy.
[5] It is not generally recommended in children with infections because of the risk
of Reye syndrome.[5] High doses may result in ringing in the ears.[5]

A precursor to aspirin found in leaves from the willow tree has been used for its
health effects for at least 2,400 years.[7][8] In 1853, chemist Charles Fr�d�ric
Gerhardt treated the medicine sodium salicylate with acetyl chloride to produce
acetylsalicylic acid for the first time.[9] For the next fifty years, other
chemists established the chemical structure and came up with more efficient
production methods.[9]:69�75 In 1897, scientists at the Bayer company began
studying acetylsalicylic acid as a less-irritating replacement medication for
common salicylate medicines.[9]:69�75[10] By 1899, Bayer had named it "Aspirin" and
sold it around the world.[11] Aspirin's popularity grew over the first half of the
twentieth century leading to competition between many brands and formulations.[12]
The word Aspirin was Bayer's brand name; however, their rights to the trademark
were lost or sold in many countries.[12]

Aspirin is one of the most widely used medications globally, with an estimated
40,000 tonnes (44,000 tons) (50 to 120 billion pills) consumed each year.[7][13] It
is on the World Health Organization's List of Essential Medicines, the safest and
most effective medicines needed in a health system.[14] As of 2014, the wholesale
cost in the developing world is US$0.002 to US$0.025 per dose.[15] As of 2015, the
cost for a typical month of medication in the United States is less than US$25.00.
[16] It is available as a generic medication.[5] In 2016, it was the 38th most
prescribed medication in the United States, with more than 19 million

1 Medical use
1.1 Pain
1.2 Fever
1.3 Inflammation
1.4 Heart attacks and strokes
1.5 Cancer prevention
1.6 Other uses
1.7 Resistance
1.8 Dosages
2 Adverse effects
2.1 Contraindications
2.2 Gastrointestinal
2.3 Central effects
2.4 Reye's syndrome
2.5 Skin
2.6 Other adverse effects
2.7 Overdose
2.8 Interactions
3 Chemical properties
3.1 Synthesis
4 Physical properties
4.1 Polymorphism
5 Mechanism of action
5.1 Discovery of the mechanism
5.2 Prostaglandins and thromboxanes
5.3 COX-1 and COX-2 inhibition
5.4 Additional mechanisms
6 Pharmacokinetics
7 History
7.1 Trademark
7.2 Compendial status
8 Veterinary medicine
8.1 Cats and dogs
8.2 Horses
9 See also
10 References
11 External links
Medical use
Aspirin is used in the treatment of a number of conditions, including fever, pain,
rheumatic fever, and inflammatory conditions, such as rheumatoid arthritis,
pericarditis, and Kawasaki disease.[18] Lower doses of aspirin have also been shown
to reduce the risk of death from a heart attack, or the risk of stroke in people
who are at high risk or who have cardiovascular disease, but not in elderly people
who are otherwise healthy.[19][20][21][22][23] There is some evidence that aspirin
is effective at preventing colorectal cancer, though the mechanisms of this effect
are unclear.[24] In the United States, low-dose aspirin is deemed reasonable in
those between 50 and 70 years old who have a risk of cardiovascular disease over
10%, are not at an increased risk of bleeding, and are otherwise healthy.[25]


Aspirin 325 milligrams (5 grains) for pain

Uncoated aspirin tablets, consisting of about 90% acetylsalicylic acid, along with
a minor amount of inert fillers and binders
Aspirin is an effective analgesic for acute pain, although it is generally
considered inferior to ibuprofen because aspirin is more likely to cause
gastrointestinal bleeding.[26] Aspirin is generally ineffective for those pains
caused by muscle cramps, bloating, gastric distension, or acute skin irritation.
[27] As with other NSAIDs, combinations of aspirin and caffeine provide slightly
greater pain relief than aspirin alone.[28] Effervescent formulations of aspirin
relieve pain faster than aspirin in tablets,[29] which makes them useful for the
treatment of migraines.[30] Topical aspirin may be effective for treating some
types of neuropathic pain.[31]