8-hour Bayer;A.S.A. Empirin;Acenterine;Acesal;Acetal;Aceticyl;Acetisal;Acetol;Acetonyl;Acetophen;Acetosal;Acetosalin;Acetylin;Acetylsal;Acimetten;Acisal;Acylpyrin;Adiro;Asagran;Asatard;Ascoden-30;Aspalon;Aspec;Aspergum;Aspirdrops;Aspirin (Bayer);Aspirine;Aspro;Asteric;Bayer Extra Strength Aspirin For Migraine Pain;Benaspir;Bi-prin;Bialpirina;Bialpirinia;Bufferin;Caprin;Cemirit;Claradin;Clariprin;Colfarit;Contrheuma retard;Coricidin;Crystar;Decaten;Delgesic;Dolean pH 8;Duramax;Easprin;ECM;Ecolen;Ecotrin;Empirin;Endydol;Entericin;Enterophen;Enterosarein;Enterosarine;Entrophen;Extren;Globentyl;Globoid;Helicon;Idragin;Levius;Measurin;Micristin;Neuronika;Novid;Nu-seals;Nu-seals aspirin;Persistin;Pharmacin;Pirseal;Polopiryna;Premaspin;Rheumintabletten;Rhodine;Rhonal;Salacetin;Salcetogen;Saletin;Solfrin;Solprin;Solprin acid;Solpyron;Spira-Dine;St. Joseph;St. Joseph Aspirin for Adults;Supac;Tasprin;Temperal;Triaminicin;Triple-sal;Vanquish;Xaxa;Yasta;

2-Acetoxybenzenecarboxylic acid;2-Acetoxybenzoic acid;2-Carboxyphenyl acetate;A.S.A.;Acetilsalicilico;Acetilum acidulatum;Acetosalic acid;Acetoxybenzoic acid;Acetylsalicylate;Acetylsalicylsaure (GERMAN);Acetysalicylic acid;Acide acetylsalicylique (FRENCH);Acido acetilsalicilico;Acido O-acetil-benzoico;Acidum acetylsalicylicum;ASA;Kyselina 2-acetoxybenzoova;Kyselina acetylsalicylova;O-accetylsalicylic acid;o-Acetoxybenzoic acid;O-Acetylsalicylic acid;o-Carboxyphenyl acetate;Salicylic acid acetate;Salicylic acid, acetate;

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. Acetylsalicylic acid also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5)

• Bayer healthcare llc

• A-S Medication Solutions LLC
• BASF Corp.
• Excellium Pharmaceutical Inc.
• Harvest Pharmaceuticals Inc.
• Kaiser Foundation Hospital
• Major Pharmaceuticals
• Mckesson Corp.
• Par Pharmaceuticals
• Prepak Systems Inc.
• Rosedale Therapeutics
• Time-Cap Labs
• United Research Laboratories Inc.

Synthesis Reference

Not Available

General Reference

Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. Pubmed Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. Pubmed Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. Pubmed Randomised trial of intravenous streptokinase, oral aspirin, both, or neither among 17,187 cases of suspected acute myocardial infarction: ISIS-2. ISIS-2 (Second International Study of Infarct Survival) Collaborative Group. Lancet. 1988 Aug 13;2(8607):349-60. Pubmed Dorsch MP, Lee JS, Lynch DR, Dunn SP, Rodgers JE, Schwartz T, Colby E, Montague D, Smyth SS: Aspirin resistance in patients with stable coronary artery disease with and without a history of myocardial infarction. Ann Pharmacother. 2007 May;41(5):737-41. Epub 2007 Apr 24. Pubmed

Type	small molecule

Classes

Benzoates Salicylates and Derivatives Phenylacetates

Substructures

Carboxylic Acids and Derivatives Hydroxy Compounds Benzyl Alcohols and Derivatives Acetates Benzoates Salicylates and Derivatives Phenols and Derivatives Phenylacetates Ethers Benzene and Derivatives Aromatic compounds Anisoles Benzoyl Derivatives Phenyl Esters

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.
Pharmacodynamics	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.
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 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.
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.
Volume of distribution	Not Available
Protein binding	High (99.5%) to albumin. Decreases as plasma salicylate concentration increases, with reduced plasma albumin concentration or renal dysfunction, and during pregnancy.
Metabolism	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. Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us. Substrate Enzymes Product Acetylsalicylic acid 1-Salicylate glucuronide Details
Route of elimination	Not Available
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.
Clearance	Not Available
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
Pathways	Pathway Name SMPDB ID Acetylsalicylic Acid Pathway SMP00083

Properties
State	solid
Experimental Properties	Property Value Source melting point 135 °C PhysProp boiling point 140 °C Not Available water solubility 4600 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.19 HANSCH,C ET AL. (1995) Caco2 permeability -5.06 ADME Research, USCD pKa 3.49 (at 25 °C) MERCK INDEX (1983)
Predicted Properties	Property Value Source water solubility 1.46e+00 g/l ALOGPS logP 1.43 ALOGPS logP 1.24 ChemAxon logS -2.1 ALOGPS pKa (strongest acidic) 3.41 ChemAxon pKa (strongest basic) -7.1 ChemAxon physiological charge -1 ChemAxon hydrogen acceptor count 3 ChemAxon hydrogen donor count 1 ChemAxon polar surface area 63.6 ChemAxon rotatable bond count 3 ChemAxon refractivity 44.45 ChemAxon polarizability 17.1 ChemAxon

Drug	Interaction
Acenocoumarol	Acetylsalicylic acid increases the effect of the anticoagulant, acenocoumarol.
Acetazolamide	Acetylsalicylic acid at high dose increases the effect of the carbonic anhydrase inhibitor, acetazolamide.
Acetohexamide	Acetylsalicylic acid increases the effect of sulfonylurea, acetohexamide.
Anisindione	Acetylsalicylic acid increases effect of the anticoagulant, anisindione.
Azilsartan medoxomil	Increases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
Betamethasone	The corticosteroid, betamethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
Chlorpropamide	Acetylsalicylic acid may increase the effect of the sulfonylurea, chlorpropamide.
Cortisone acetate	The corticosteroid, cortisone acetate, may decrease the effect of the salicylate, acetylsalicylic acid.
Dexamethasone	The corticosteroid, dexamethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
Dichlorphenamide	Acetylsalicylic acid at high dose increases the effect of the carbonic anhydrase inhibitor, dichlorphenamide.
Dicumarol	Acetylsalicylic acid increases effect of the anticoagulant, dicumarol.
Eltrombopag	Decreases metabolism, will increase effect/level of eltrombopag.
Fludrocortisone	The corticosteroid, fludrocortisone, may decrease the effect of the salicylate, acetylsalicylic acid.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Gliclazide	Acetylsalicylic acid increases the effect of the sulfonylurea, gliclazide.
Glipizide	Acetylsalicylic acid increases the effect of the sulfonylurea, glipizide.
Glisoxepide	Acetylsalicylic acid increases the effect of the sulfonylurea, glisoxepide.
Glyburide	Acetylsalicylic acid increases the effect of the sulfonylurea, glibenclamide.
Glycodiazine	Acetylsalicylic acid increases the effect of sulfonylurea, glycodiazine.
Griseofulvin	Griseofulvin may decrease the efficacy of acetylsalicylic acid.
Heparin	Increased risk of bleeding.
Homoharringtonine	Avoid combination with acetylsalicylic acid due to the potential enhancement of homoharringtonine associated bleeding-related adverse effects. Specifically it is suggested to avoid this combination in patients with a platelet count of less than 50,000/uL.
Hydrocortisone	The corticosteroid, hydrocortisone, may decrease the effect of the salicylate, acetylsalicylic acid.
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.
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.
Ketorolac	Acetylsalicylic acid may increase the adverse GI effects ketorolac.
Methazolamide	Acetylsalicylic acid at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
Methotrexate	Acetylsalicylic acid increases the effect and toxicity of methotrexate.
Methylprednisolone	The corticosteroid, methylprednisolone, may decrease the effect of the salicylate, acetylsalicylic acid.
Paramethasone	The corticosteroid, paramethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
Prednisolone	The corticosteroid, prednisolone, may decrease the effect of the salicylate, acetylsalicylic acid.
Prednisone	The corticosteroid, prednisone, may decrease the effect of the salicylate, acetylsalicylic acid.
Probenecid	Acetylsalicylic acid decreases the uricosuric effect of probenecid.
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.
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.
Tiaprofenic acid	Increased risk of gastrointestinal bleeding.
Ticlopidine	Increased effect of ticlopidine
Tolazamide	Acetylsalicylic acid increases the effect of the sulfonylurea, tolazamide.
Tolbutamide	Acetylsalicylic acid increases the effect of the sulfonylurea, tolbutamide.
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.
Trandolapril	Acetylsalicylic acid may reduce the efficacy of Trandolapril. Monitor for changes in Trandolapril efficacy if Acetylsalicylic acid is initiated, discontinued or dose changed.
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.
Triamcinolone	The corticosteroid, triamcinolone, may decrease the effect of the salicylate, acetylsalicylic acid.
Valproic Acid	Acetylsalicylic acid increases the effect of valproic acid.
Warfarin	The antiplatelet effects of acetylsalicylic acid may increase the bleed risk associated with warfarin.

• Avoid alcohol, alcohol appears to cause a 50 to 100% increases in ASA serum levels.
• Take with a full glass of water.
• Take with food to reduce gastric irritation.