QuickView for Acetylsalicylic acid (compound)

Summary
General Info

PubChem

PubChem Compound 21975

Name:	Aspirin
PubChem Compound ID:	21975
Description:	The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5)
Molecular formula:	C₁₉H₁₈CaN₂O₉
Molecular weight:	458.432 g/mol
Synonyms:	CARBASPIRIN CALCIUM; 52080-78-1; Salicylic acid acetate calcium salt, compound with urea (1:1) complex; Carbasalate calcium; EINECS 227-273-0; Carbasalatum calcicum [INN-Latin]; D03385; Carbasalato calcico [INN-Spanish]; Carbaspirin calcium [USAN]; Carbaspirin calcium (USAN). show more » CARBASPIRIN CALCIUM; 52080-78-1; Salicylic acid acetate calcium salt, compound with urea (1:1) complex; Carbasalate calcium; EINECS 227-273-0; Carbasalatum calcicum [INN-Latin]; D03385; Carbasalato calcico [INN-Spanish]; Carbaspirin calcium [USAN]; Carbaspirin calcium (USAN); 5749-67-7; Benzoic acid, 2-(acetyloxy)-, calcium salt, compd. with urea (1:1); Carbasalate calcique [INN-French]; Calcium acetylsalicylate complex with urea; Carbasalatcalcium show less «

DrugBank

Identification

Name:	Aspirin
Name (isomeric):	DB00945
Drug Type:	small molecule
Description:	The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5)
Synonyms:	Acide acetylsalicylique (FRENCH); Acetilum acidulatum; Acido O-acetil-benzoico; o-Carboxyphenyl acetate; O-Acetylsalicylic acid; O-accetylsalicylic acid; Kyselina acetylsalicylova; Acetoxybenzoic acid; o-Acetoxybenzoic acid; 2-Acetoxybenzenecarboxylic acid. show more » Acide acetylsalicylique (FRENCH); Acetilum acidulatum; Acido O-acetil-benzoico; o-Carboxyphenyl acetate; O-Acetylsalicylic acid; O-accetylsalicylic acid; Kyselina acetylsalicylova; Acetoxybenzoic acid; o-Acetoxybenzoic acid; 2-Acetoxybenzenecarboxylic acid; A.S.A.; Kyselina 2-acetoxybenzoova; Acetosalic acid; ASA; Acetilsalicilico; Acetylsalicylsaure (GERMAN); Acetylsalicylate; Acetysalicylic acid; Salicylic acid, acetate; 2-Carboxyphenyl acetate; Salicylic acid acetate; 2-Acetoxybenzoic acid; Acidum acetylsalicylicum; Acido acetilsalicilico show less «
Brand:	Bufferin, Delgesic, Levius, Rhodine, Caprin, Enterosarein, Acetonyl, Acetosal, Solprin, Tasprin, Persistin, Dolean pH 8, Solprin acid, Salacetin, Entrophen, 8-hour Bayer, Acetylin, Bialpirina, Endydol, Asteric, Enterosarine, Aspirine, Ecolen, Triaminicin, Helicon, Globentyl, Acetosalin, Saletin, Acetylsal, Adiro, Decaten, Triple-sal, Aspirdrops, Acetal, Coricidin, Idragin, Spira-Dine, Rhonal, Asatard, Benaspir, Vanquish, Salcetogen, Polopiryna, Extren, Crystar, Acenterine, Acetisal, Acisal, Bialpirinia, Empirin, Aceticyl, Aspec, Measurin, Yasta, Xaxa, Rheumintabletten, Acimetten, Pharmacin, Bayer Extra Strength Aspirin For Migraine Pain, Aspirin, Clariprin, Acetophen, Nu-seals aspirin, Acetol, Easprin, Entericin, Colfarit, Supac, St. Joseph Aspirin for Adults, Solfrin, Pirseal, Acesal, ECM, Aspalon, Premaspin, Claradin, Enterophen, Micristin, A.S.A. Empirin, Ecotrin, Globoid, Temperal, Aspergum, Nu-seals, Cemirit, Contrheuma retard, Novid, Ascoden-30, Asagran, Solpyron, Aspro, St. Joseph, Acylpyrin, Duramax, Bi-prin, Neuronika
Brand name mixture:	Aspirin Plus Stomach Guard Extra Strength(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide), Aspirin with Stomach Guard(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide), Extra Strength Aspirin Backache(Acetylsalicylic Acid + Methocarbamol), Aspirin Plus Stomach Guard Ext.Stgth.Capl... show more » Aspirin Plus Stomach Guard Extra Strength(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide), Aspirin with Stomach Guard(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide), Extra Strength Aspirin Backache(Acetylsalicylic Acid + Methocarbamol), Aspirin Plus Stomach Guard Ext.Stgth.Caplet(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide), Aspirin Plus Stomach Guard Tab(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide), Aspirin with Stomach Guard Extra Strength - Tab(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide), Aspirin Plus Stomach Guard(Acetylsalicylic Acid + Calcium Carbonate + Magnesium Carbonate + Magnesium Oxide) show less «
Category:	Anticoagulants, Cyclooxygenase Inhibitors, Salicylates, Fibrinolytic Agents, Platelet Aggregation Inhibitors
CAS number:	50-78-2

Pharmacology

Indication:	For use in the temporary relief of various forms of pain, inflammation associated with various conditions (including rheumatoid arthritis, juvenile rheumatoid arthritis, systemic lupus erythematosus, osteoarthritis, and ankylosing spondylitis), and is also used to reduce the risk of death and/or nonfatal myocardial infarction in patients with a previous infarction or unstable angina pectoris.
Pharmacology:	Acetylsalicylic acid is an analgesic, antipyretic, antirheumatic, and anti-inflammatory agent. Acetylsalicylic acid's mode of action as an antiinflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. Acetylsalicylic acid appears to produce analgesia by virtue of both a peripheral and CNS effect. Peri... show more » Acetylsalicylic acid is an analgesic, antipyretic, antirheumatic, and anti-inflammatory agent. Acetylsalicylic acid's mode of action as an antiinflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. Acetylsalicylic acid appears to produce analgesia by virtue of both a peripheral and CNS effect. Peripherally, acetylsalicylic acid acts by inhibiting the synthesis and release of prostaglandins. Acting centrally, it would appear to produce analgesia at a hypothalamic site in the brain, although the mode of action is not known. Acetylsalicylic acid also acts on the hypothalamus to produce antipyresis; heat dissipation is increased as a result of vasodilation and increased peripheral blood flow. Acetylsalicylic acid's antipyretic activity may also be related to inhibition of synthesis and release of prostaglandins. show less «
Mechanism of Action:	The analgesic, antipyretic, and anti-inflammatory effects of acetylsalicylic acid are due to actions by both the acetyl and the salicylate portions of the intact molecule as well as by the active salicylate metabolite. Acetylsalicylic acid directly and irreversibly inhibits the activity of both types of cyclooxygenase (COX-1 and COX-2) to decrease ... show more » The analgesic, antipyretic, and anti-inflammatory effects of acetylsalicylic acid are due to actions by both the acetyl and the salicylate portions of the intact molecule as well as by the active salicylate metabolite. Acetylsalicylic acid directly and irreversibly inhibits the activity of both types of cyclooxygenase (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. This makes acetylsalicylic acid different from other NSAIDS (such as diclofenac and ibuprofen) which are reversible inhibitors. Salicylate may competitively inhibit prostaglandin formation. Acetylsalicylic acid's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms; the therapeutic effects are not due to pituitary-adrenal stimulation. The platelet aggregation-inhibiting effect of acetylsalicylic acid specifically involves the compound's ability to act as an acetyl donor to cyclooxygenase; the nonacetylated salicylates have no clinically significant effect on platelet aggregation. Irreversible acetylation renders cyclooxygenase inactive, thereby preventing the formation of the aggregating agent thromboxane A2 in platelets. Since platelets lack the ability to synthesize new proteins, the effects persist for the life of the exposed platelets (7-10 days). Acetylsalicylic acid may also inhibit production of the platelet aggregation inhibitor, prostacyclin (prostaglandin I2), by blood vessel endothelial cells; however, inhibition prostacyclin production is not permanent as endothelial cells can produce more cyclooxygenase to replace the non-functional enzyme. show less «
Absorption:	Absorption is generally rapid and complete following oral administration but may vary according to specific salicylate used, dosage form, and other factors such as tablet dissolution rate and gastric or intraluminal pH.
Protein binding:	High (99.5%) to albumin. Decreases as plasma salicylate concentration increases, with reduced plasma albumin concentration or renal dysfunction, and during pregnancy.
Biotransformation:	Acetylsalicylic acid is rapidly hydrolyzed primarily in the liver to salicylic acid, which is conjugated with glycine (forming salicyluric acid) and glucuronic acid and excreted largely in the urine.
Half Life:	The plasma half-life is approximately 15 minutes; that for salicylate lengthens as the dose increases: doses of 300 to 650 mg have a half-life of 3.1 to 3.2 hours; with doses of 1 gram, the half-life is increased to 5 hours and with 2 grams it is increased to about 9 hours.
Toxicity:	Oral, mouse: LD₅₀ = 250 mg/kg; Oral, rabbit: LD₅₀ = 1010 mg/kg; Oral, rat: LD₅₀ = 200 mg/kg. Effects of overdose include: tinnitus, abdominal pain, hypokalemia, hypoglycemia, pyrexia, hyperventilation, dysrhythmia, hypotension, hallucination, renal failure, confusion, seizure, coma, and death.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take with food to reduce gastric irritation.

Avoid alcohol, alcohol appears to cause a 50 to 100% increases in ASA serum levels.

Take with a full glass of water.

Drug interaction:

Methazolamide	Acetylsalicylic acid at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
Tiaprofenic acid	Increased risk of gastrointestinal bleeding.
Methotrexate	Acetylsalicylic acid increases the effect and toxicity of methotrexate.
Glipizide	Acetylsalicylic acid increases the effect of the sulfonylurea, glipizide.
Paramethasone	The corticosteroid, paramethasone, may decrease the effect of the salicylate, acetylsalicylic acid.

Methazolamide	Acetylsalicylic acid at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
Tiaprofenic acid	Increased risk of gastrointestinal bleeding.
Methotrexate	Acetylsalicylic acid increases the effect and toxicity of methotrexate.
Glipizide	Acetylsalicylic acid increases the effect of the sulfonylurea, glipizide.
Paramethasone	The corticosteroid, paramethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
Tolazamide	Acetylsalicylic acid increases the effect of the sulfonylurea, tolazamide.
Dexamethasone	The corticosteroid, dexamethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
Cortisone acetate	The corticosteroid, cortisone acetate, may decrease the effect of the salicylate, acetylsalicylic acid.
Ketoprofen	Concomitant therapy of the NSAID, ketoprofen, and acetylsalicylic acid may result in additive adverse/toxic effects (e.g. GI bleeding). The NSAID may also limit the cardioprotective effect of acetylsalicylic acid. Occasional concomitant use may not cause clinically significant problems, but regular, frequent concomitant therapy is not recommended.
Treprostinil	The prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Acetylsalicylic acid. Monitor for increased bleeding during concomitant thearpy.
Prednisolone	The corticosteroid, prednisolone, may decrease the effect of the salicylate, acetylsalicylic acid.
Acenocoumarol	Acetylsalicylic acid increases the effect of the anticoagulant, acenocoumarol.
Triamcinolone	The corticosteroid, triamcinolone, may decrease the effect of the salicylate, acetylsalicylic acid.
Divalproex sodium	Acetylsalicylic acid increases the effect of divalproex sodium.
Tolbutamide	Acetylsalicylic acid increases the effect of the sulfonylurea, tolbutamide.
Acetazolamide	Acetylsalicylic acid at high dose increases the effect of the carbonic anhydrase inhibitor, acetazolamide.
Acetohexamide	Acetylsalicylic acid increases the effect of sulfonylurea, acetohexamide.
Warfarin	The antiplatelet effects of acetylsalicylic acid may increase the bleed risk associated with warfarin.
Chlorpropamide	Acetylsalicylic acid may increase the effect of the sulfonylurea, chlorpropamide.
Hydrocortisone	The corticosteroid, hydrocortisone, may decrease the effect of the salicylate, acetylsalicylic acid.
Heparin	Increased risk of bleeding.
Prednisone	The corticosteroid, prednisone, may decrease the effect of the salicylate, acetylsalicylic acid.
Ticlopidine	Increased effect of ticlopidine
Probenecid	Acetylsalicylic acid decreases the uricosuric effect of probenecid.
Methylprednisolone	The corticosteroid, methylprednisolone, may decrease the effect of the salicylate, acetylsalicylic acid.
Tolmetin	Additive adverse effects increase the risk of gastrointestinal bleeding. Possible decrease in the cardioprotective effect of acetylsalicylic acid. Monitor for increased bleeding risk during concomitant therapy.
Glisoxepide	Acetylsalicylic acid increases the effect of the sulfonylurea, glisoxepide.
Valproic Acid	Acetylsalicylic acid increases the effect of valproic acid.
Fludrocortisone	The corticosteroid, fludrocortisone, may decrease the effect of the salicylate, acetylsalicylic acid.
Trandolapril	Acetylsalicylic acid may reduce the efficacy of Trandolapril. Monitor for changes in Trandolapril efficacy if Acetylsalicylic acid is initiated, discontinued or dose changed.
Anisindione	Acetylsalicylic acid increases effect of the anticoagulant, anisindione.
Gliclazide	Acetylsalicylic acid increases the effect of the sulfonylurea, gliclazide.
Ibuprofen	Concomitant therapy of the NSAID, ketoprofen, and acetylsalicylic acid may result in additive adverse/toxic effects (e.g. GI bleeding). The NSAID may also limit the cardioprotective effect of acetylsalicylic acid. Occasional concomitant use may not cause clinically significant problems, but regular, frequent concomitant therapy is not recommended.
Dicumarol	Acetylsalicylic acid increases effect of the anticoagulant, dicumarol.
Betamethasone	The corticosteroid, betamethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
Glyburide	Acetylsalicylic acid increases the effect of the sulfonylurea, glibenclamide.
Glycodiazine	Acetylsalicylic acid increases the effect of sulfonylurea, glycodiazine.
Sulindac	Risk of additive toxicity (e.g. bleed risk). Acetylsalicylic acid may decrease the serum concentration of sulindac. Sulindac may counteract the cardioprotective effects of acetylsalicylic acid. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of both agents if the interacting agent is initiated, discontinued or dose changed.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Griseofulvin	Griseofulvin may decrease the efficacy of acetylsalicylic acid.
Ketorolac	Acetylsalicylic acid may increase the adverse GI effects ketorolac.
Dichlorphenamide	Acetylsalicylic acid at high dose increases the effect of the carbonic anhydrase inhibitor, dichlorphenamide.
Telmisartan	Concomitant use of Telmisartan and Acetylsalicylic acid may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.

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Targets

Prostaglandin G/H synthase 1

Prostaglandin G/H synthase 2

Aldo-keto reductase family 1 member C1

Enzymes

Cytochrome P450 2C19

Cytochrome P450 2C8

Cytochrome P450 2C9

Transporters

Solute carrier family 22 member 6

Multidrug resistance protein 1

Solute carrier family 22 member 7

Carriers

Serum albumin