Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to reduce pain, fever, or inflammation. Specific inflammatory conditions which aspirin is used to treat include [[Kawasaki disease]], [[pericarditis]], and [[rheumatic fever]]. Aspirin is also used long-term to help prevent further heart attacks, [[ischemic stroke]], and blood clots in people at high risk.
| legal_AU = OTC
| legal_AU_comment = Schedule 2, 4, 5, 6
| legal_BR =
| legal_BR_comment =
| legal_CA = OTC
| legal_CA_comment =
| legal_DE =
| legal_DE_comment =
| legal_NZ =
| legal_NZ_comment =
| legal_UK = GSL
| legal_UK_comment =
| legal_US = OTC
| legal_US_comment = Rx-only
| legal_UN =
| legal_UN_comment =
| legal_status =
<!-- Pharmacokinetic data -->
==History==
| bioavailability = 80–100%
[[File:Aspirine-1923.jpg|thumb|left|Aspirin advertisement from 1923]]
| protein_bound = 80–90%
| metabolism = Liver (CYP2C19 and possibly CYP3A), some hydrolysed to salicylate in the gut wall
| metabolites =
| onset =
| elimination_half-life = Dose-dependent; 2–3 h for low doses (100 mg or less), 15–30 h for larger doses
The use of aspirin dates back to ancient times when extracts of [[willow bark]] were used for pain relief. The active ingredient, salicin, was identified in the 19th century, and acetylsalicylic acid was synthesized by [[Felix Hoffmann]] at [[Bayer]] in 1897.
'''Aspirin''', scientifically known as '''acetylsalicylic acid''', stands as one of the most ubiquitously employed [[analgesic]] and [[antipyretic]] medications across the globe, boasting over a century of clinical application.
Aspirin is a [[salicylate]] drug, and its chemical formula is C₉H₈O₄. It is an ester of [[salicylic acid]] and [[acetic anhydride]].
== Introduction ==
==Mechanism of Action==
Derived from salicylate, Aspirin has not only served as a remedy for pain and fever but has demonstrated efficacy in lowering risks associated with cardiovascular events like heart attacks, clot-induced strokes, and circulatory complications. Many healthcare professionals vouch for and prescribe aspirin for its cardioprotective qualities, especially for patients diagnosed with cardiovascular diseases or those with a history of cardiac or cerebrovascular events.
[[File:PTGS2 inhibited by Aspirin.png|thumb|left|Aspirin inhibits the enzyme PTGS2]]
== Benefits and Risks ==
Aspirin works by inhibiting the enzyme [[cyclooxygenase]] (COX), which results in a decreased formation of [[prostaglandins]] and [[thromboxanes]]. This inhibition is irreversible, which is why aspirin has a prolonged effect on platelet function.
=== Benefits ===
* '''Cardiovascular Protection:''' Daily consumption can aid in decreasing the chances of heart attacks, clot-associated strokes, and circulatory disturbances.
* '''Neurological Advantages:''' Those with compromised cerebral circulation might benefit from aspirin therapy.
=== Risks ===
Despite its therapeutic advantages, aspirin isn't devoid of potential risks. Complications may include:
* Stomach bleeding
* Cerebral hemorrhage
* Kidney dysfunction
* Stroke susceptibility
It's paramount that patients discuss with health professionals to strike a balance between benefits and potential adverse reactions.
==Synthesis==
[[File:Aspirin_synthesis.svg|thumb|right|Synthesis of aspirin]]
== Liver Safety ==
Aspirin is synthesized through the acetylation of salicylic acid with acetic anhydride. The reaction is catalyzed by an acid, such as sulfuric acid or phosphoric acid.
High doses of aspirin might pave the way for liver injuries. This includes marked elevations in serum aminotransferase, occasionally accompanied by jaundice. Particularly vulnerable are children with febrile illnesses; they might develop [[Reye syndrome]] upon exposure to even lower doses.
== Mechanism of Action ==
===Reaction Mechanism===
Classified under [[NSAID|nonsteroidal anti-inflammatory drugs (NSAIDs)]], aspirin acts by inhibiting cyclooxygenases ([[Cox-1]] and [[Cox-2]]), enzymes responsible for proinflammatory prostaglandin synthesis, which are mediators for pain and inflammation. Unique to aspirin is its irreversible and noncompetitive inhibition of Cox-1, making its effects relatively persistent. This potent and prolonged action also accounts for aspirin's association with gastric irritations and bleeding.
[[File:Acetylation of salicylic acid, mechanism.png|thumb|left|Mechanism of acetylation of salicylic acid]]
== Clinical Uses ==
The acetylation of salicylic acid involves the transfer of an acetyl group from acetic anhydride to the hydroxyl group of salicylic acid, forming aspirin and acetic acid as a byproduct.
Aspirin's therapeutic application spans:
* Mild to moderate pain relief stemming from diverse causes including headaches, traumas, menstrual cramps, and various arthritic conditions.
* Management of juvenile rheumatoid arthritis, systemic lupus erythematosus, rheumatoid arthritis, acute rheumatic fever, and [[Kawasaki disease]].
* Fever management, albeit not recommended for young individuals due to the Reye syndrome risk.
* Prophylactic use in atherosclerosis and post-coronary interventions, typically at a dose of 81 mg daily.
== FDA Approval ==
==Medical Uses==
The US welcomed aspirin's clinical introduction in the early 20th century. Presently, it graces many medicine cabinets as an over-the-counter staple, available in its pure form or combined with various other drugs.
Aspirin is used for its analgesic, antipyretic, and anti-inflammatory properties. It is also used in low doses to reduce the risk of heart attack and stroke.
== Dosage and Administration ==
==Side Effects==
Typical aspirin dosage ranges between 330 to 660 mg, administered every 4 to 6 hours. For its antiplatelet benefits, particularly in preventing atherosclerotic complications, 81 mg once daily is the norm.
Common side effects include [[gastrointestinal bleeding]], [[ulceration]], and [[tinnitus]]. Aspirin should be used with caution in people with [[asthma]] or [[peptic ulcer disease]].
== Brand Names ==
==Commercial Availability==
Aspirin is marketed under various commercial names, including:
[[File:Old_Package_of_Aspirin.jpg|thumb|right|Old package of aspirin]]
** [[Bayer’s aspirin]]
[[File:Bayer Aspirin and store-brand generic on Canadian drugstore shelf.jpg|thumb|left|Bayer aspirin and generic aspirin on a store shelf]]
** [[Alka seltzer]]
** [[Anacin]]
** [[Ascriptin]]
** [[Aspergum]]
** [[BC powder]]
** Bufferin
** [[Ecotrin]]
** [[Excedrin]]
** [[Stanback]]
== See Also ==
Aspirin is available over-the-counter in many countries and is sold under various brand names, including Bayer Aspirin.
* [[Analgesic]]
* [[Antipyretic]]
* [[NSAID]]
* [[Cox-1]]
* [[Cox-2]]
* [[Reye syndrome]]
* [[Kawasaki disease]]
{{ATC navboxes|B01|D10|M01A|N02A}}
==Related Pages==
{{Salicylates}}
* [[Nonsteroidal anti-inflammatory drug]]
{{Prostanoid signaling modulators}}
* [[Salicylic acid]]
{{Portal bar | Medicine}}
* [[Cyclooxygenase]]
{{antithrombotic agents}}
* [[Thromboxane]]
{{coststubd}}
[[Category:Aspirin| ]]
[[Category:Analgesics]]
[[Category:1897 in Germany]]
[[Category:Nonsteroidal anti-inflammatory drugs]]
[[Category:1897 in science]]
[[Category:Acetate esters]]
[[Category:Acetylsalicylic acids]]
[[Category:Antiplatelet drugs]]
[[Category:Antiplatelet drugs]]
[[Category:Drugs developed by Bayer]]
[[Category:Brands that became generic]]
[[Category:Chemical substances for emergency medicine]]
[[Category:Commercialization of traditional medicines]]
[[Category:Covalent inhibitors]]
[[Category:Equine medications]]
[[Category:German inventions]]
[[Category:Hepatotoxins]]
[[Category:Nonsteroidal anti-inflammatory drugs]]
[[Category:Salicylic acids]]
[[Category:Salicylyl esters]]
[[Category:Medications]]
[[Category:Analgesics]]
[[Category:Antipyretics]]
[[Category:NSAIDs]]
<gallery>
File:Aspirin-skeletal.svg|Aspirin
File:Aspirin-B-3D-balls.png|Aspirin
File:Aspirin synthesis.svg|Aspirin
File:Acetylation of salicylic acid, mechanism.png|Aspirin
File:PTGS2 inhibited by Aspirin.png|Aspirin
File:Aspirine-1923.jpg|Aspirin
File:Old Package of Aspirin.jpg|Aspirin
File:Bayer Aspirin and store-brand generic on Canadian drugstore shelf.jpg|Aspirin
File:Bayer and store-brand aspirin containers on US drugstore shelf.jpg|Aspirin
</gallery>
Revision as of 14:18, 21 February 2025
Aspirin
Skeletal formula of aspirin
Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to reduce pain, fever, or inflammation. Specific inflammatory conditions which aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin is also used long-term to help prevent further heart attacks, ischemic stroke, and blood clots in people at high risk.
The use of aspirin dates back to ancient times when extracts of willow bark were used for pain relief. The active ingredient, salicin, was identified in the 19th century, and acetylsalicylic acid was synthesized by Felix Hoffmann at Bayer in 1897.
Aspirin works by inhibiting the enzyme cyclooxygenase (COX), which results in a decreased formation of prostaglandins and thromboxanes. This inhibition is irreversible, which is why aspirin has a prolonged effect on platelet function.
Synthesis
Synthesis of aspirin
Aspirin is synthesized through the acetylation of salicylic acid with acetic anhydride. The reaction is catalyzed by an acid, such as sulfuric acid or phosphoric acid.
Reaction Mechanism
Mechanism of acetylation of salicylic acid
The acetylation of salicylic acid involves the transfer of an acetyl group from acetic anhydride to the hydroxyl group of salicylic acid, forming aspirin and acetic acid as a byproduct.
Medical Uses
Aspirin is used for its analgesic, antipyretic, and anti-inflammatory properties. It is also used in low doses to reduce the risk of heart attack and stroke.
