Aspirin: Difference between revisions

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{{Infobox drug
[[File:Aspirin-skeletal.svg|thumb|right|Skeletal formula of aspirin]]
| Watchedfields      = changed
| verifiedrevid      = 464364671
| drug_name          = Acetylsalicylic acid
| INN                = none
| image              = Aspirin-skeletal.svg
| image_class        = skin-invert-image
| width              = 100
| alt                =
| image2            = Aspirin-B-3D-balls.png
| width2            = 125
| alt2              =
| caption            =


<!-- Clinical data -->
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.
| pronounce          = {{IPAc-en|ə|ˌ|s|iː|t|əl|ˌ|s|æ|l|ᵻ|ˈ|s|ɪ|l|ᵻ|k}}
| tradename          = Bayer Aspirin, others
| Drugs.com          =
| MedlinePlus        = a682878
| DailyMedID        = Acetylsalicylic acid
| pregnancy_AU      = C
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = Oral, rectal
| class              = Nonsteroidal anti-inflammatory drug (NSAID)
| ATC_prefix        = A01
| ATC_suffix        = AD05
| ATC_supplemental  = {{ATC|B01|AC06}}, {{ATC|N02|BA01}}


<!-- Legal status -->
==History==
| legal_AU          = OTC
[[File:Aspirine-1923.jpg|thumb|left|Aspirin advertisement from 1923]]
| 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 -->
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.
| bioavailability    = 80–100%
| 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
| duration_of_action =
| excretion          = Urine (80–100%), sweat, saliva, feces


<!-- Identifiers -->
==Chemical Structure==
| CAS_number        = 50-78-2
[[File:Aspirin-B-3D-balls.png|thumb|right|3D ball model of aspirin]]
| CAS_supplemental  =  
| PubChem            = 2244
| IUPHAR_ligand      = 4139
| DrugBank          = DB00945
| ChemSpiderID      = 2157
| UNII              = R16CO5Y76E
| KEGG              = D00109
| KEGG2              = C01405
| ChEBI              = 15365
| ChEMBL            = 25
| NIAID_ChemDB      =
| PDB_ligand        = AIN
| synonyms          = 2-acetoxybenzoic acid, 2-(acetyloxy)benzoic acid, ''o''-acetylsalicylic acid, acetylsalicylic acid, acetyl salicylate, salicylic acid acetate, o-carboxyphenyl acetate, monoacetic acid ester of salicylic acid


<!-- Chemical and physical data -->
Aspirin is a [[salicylate]] drug, and its chemical formula is C₉H₈O₄. It is an ester of [[salicylic acid]] and [[acetic anhydride]].
| IUPAC_name        = 2-acetyloxybenzoic acid
| C                  = 9
| H                  = 8
| O                  = 4
| SMILES            = O=C(C)Oc1ccccc1C(=O)O
| StdInChI          = 1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
| StdInChIKey        = BSYNRYMUTXBXSQ-UHFFFAOYSA-N
| density            = 1.40
| melting_point      = 135
| boiling_point      = 140 (decomposes)
| solubility        = 3 g/L
}}


'''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.
==Mechanism of Action==
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.


== Introduction ==
==Synthesis==
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:Aspirin_synthesis.svg|thumb|right|Synthesis of aspirin]]


== Benefits and Risks ==
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.
=== 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.
===Reaction Mechanism===
[[File:Acetylation of salicylic acid, mechanism.png|thumb|left|Mechanism of acetylation of salicylic acid]]


== Liver Safety ==
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.
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 ==
==Medical Uses==
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.
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.


== Clinical Uses ==
==Side Effects==
Aspirin's therapeutic application spans:
Common side effects include [[gastrointestinal bleeding]], [[ulceration]], and [[tinnitus]]. Aspirin should be used with caution in people with [[asthma]] or [[peptic ulcer disease]].
* 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 ==
==Commercial Availability==
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.
[[File:Old_Package_of_Aspirin.jpg|thumb|right|Old package of aspirin]]
[[File:Bayer Aspirin and store-brand generic on Canadian drugstore shelf.jpg|thumb|left|Bayer aspirin and generic aspirin on a store shelf]]


== Dosage and Administration ==
Aspirin is available over-the-counter in many countries and is sold under various brand names, including Bayer Aspirin.
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.


== Brand Names ==
==Related Pages==
Aspirin is marketed under various commercial names, including:
* [[Nonsteroidal anti-inflammatory drug]]
** [[Bayer’s aspirin]]
* [[Salicylic acid]]
** [[Alka seltzer]]
* [[Cyclooxygenase]]
** [[Anacin]]
* [[Thromboxane]]
** [[Ascriptin]]
** [[Aspergum]]
** [[BC powder]]
** Bufferin
** [[Ecotrin]]
** [[Excedrin]]
** [[Stanback]]
 
== See Also ==
* [[Analgesic]]
* [[Antipyretic]]
* [[NSAID]]
* [[Cox-1]]
* [[Cox-2]]
* [[Reye syndrome]]
* [[Kawasaki disease]]
 
{{ATC navboxes|B01|D10|M01A|N02A}}
{{Salicylates}}
{{Salicylates}}
{{Prostanoid signaling modulators}}
{{Prostanoid signaling modulators}}
{{Portal bar | Medicine}}
{{Portal bar | Medicine}}
{{antithrombotic agents}}
{{coststubd}}
[[Category:Aspirin| ]]
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[[Category:1897 in Germany]]
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[[Category:Salicylic acids]]
[[Category:Salicylic acids]]
[[Category:Salicylyl esters]]
[[Category:Salicylyl esters]]
[[Category:Medications]]
[[Category:Analgesics]]
[[Category:Analgesics]]
[[Category:Antipyretics]]
[[Category:Nonsteroidal anti-inflammatory drugs]]
[[Category:NSAIDs]]
[[Category:Antiplatelet drugs]]
<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>

Latest revision as of 15:55, 21 February 2025

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.

History[edit]

Aspirin advertisement from 1923

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.

Chemical Structure[edit]

3D ball model of aspirin

Aspirin is a salicylate drug, and its chemical formula is C₉H₈O₄. It is an ester of salicylic acid and acetic anhydride.

Mechanism of Action[edit]

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[edit]

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[edit]

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[edit]

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.

Side Effects[edit]

Common side effects include gastrointestinal bleeding, ulceration, and tinnitus. Aspirin should be used with caution in people with asthma or peptic ulcer disease.

Commercial Availability[edit]

Old package of aspirin
Bayer aspirin and generic aspirin on a store shelf

Aspirin is available over-the-counter in many countries and is sold under various brand names, including Bayer Aspirin.

Related Pages[edit]

Salicylates


Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)
EP (E2)
EP1
EP2
EP3
EP4
Unsorted
FP (F2α)
IP (I2)
TP (TXA2)
Enzyme
(inhibitors)
COX
(PTGS )
* Salicylic acids: Aloxiprin
PGD2S
PGES
PGFS
PGI2S
Others
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