Identification

Name
Acetylsalicylic acid
Commonly known or available as Aspirin
Accession Number
DB00945
Description

Also known as Aspirin, acetylsalicylic acid (ASA) is a commonly used drug for the treatment of pain and fever due to various causes. Acetylsalicylic acid has both anti-inflammatory and antipyretic effects. This drug also inhibits platelet aggregation and is used in the prevention of blood clots stroke, and myocardial infarction (MI) Label.

Interestingly, the results of various studies have demonstrated that long-term use of acetylsalicylic acid may decrease the risk of various cancers, including colorectal, esophageal, breast, lung, prostate, liver and skin cancer 15. Aspirin is classified as a non-selective cyclooxygenase (COX) inhibitor 11,14 and is available in many doses and forms, including chewable tablets, suppositories, extended release formulations, and others 19.

Acetylsalicylic acid is a very common cause of accidental poisoning in young children. It should be kept out of reach from young children, toddlers, and infants Label.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 180.1574
Monoisotopic: 180.042258744
Chemical Formula
C9H8O4
Synonyms
  • 2-Acetoxybenzenecarboxylic acid
  • 2-Acetoxybenzoic acid
  • Acetylsalicylate
  • Acetylsalicylsäure
  • acide 2-(acétyloxy)benzoïque
  • Acide acétylsalicylique
  • ácido acetilsalicílico
  • Acidum acetylsalicylicum
  • ASA
  • Aspirin
  • Aspirina
  • Azetylsalizylsäure
  • o-acetoxybenzoic acid
  • O-acetylsalicylic acid
  • o-carboxyphenyl acetate
  • Polopiryna
  • Salicylic acid acetate
External IDs
  • BAY1019036
  • NSC-27223
  • NSC-406186

Pharmacology

Indication

Pain, fever, and inflammation

Acetylsalicylic acid (ASA), in the regular tablet form (immediate-release), is indicated to relieve pain, fever, and inflammation associated with many conditions, including the flu, the common cold, neck and back pain, dysmenorrhea, headache, tooth pain, sprains, fractures, myositis, neuralgia, synovitis, arthritis, bursitis, burns, and various injuries. It is also used for symptomatic pain relief after surgical and dental procedures Label.

The extra strength formulation of acetylsalicylic acid is also indicated for the management migraine pain with photophobia (sensitivity to light) and phonophobia (sensitivity to sound)Label.

Other indications

ASA is also indicated for various other purposes, due to its ability to inhibit platelet aggregation. These include:

Reducing the risk of cardiovascular death in suspected cases of myocardial infarction (MI) Label.

Reducing the risk of a first non-fatal myocardial infarction in patients, and for reducing the risk of morbidity and mortality in cases of unstable angina and in those who have had a prior myocardial infarction Label.

For reducing the risk of transient ischemic attacks (TIA) and to prevent atherothrombotic cerebral infarction (in conjunction with other treatments) Label.

For the prevention of thromboembolism after hip replacement surgery Label.

For decreasing platelet to platelet adhesion following carotid endarterectomy, aiding in the prevention of transient ischemic attacks (TIA) Label.

Used for patients undergoing hemodialysis with a silicone rubber arteriovenous cannula inserted to prevent thrombosis at the insertion site Label.

Important note regarding use of the extended-release formulation 21

In the setting of acute myocardial infarction, or before percutaneous interventions, the extended-release form of acetylsalicylic acid should not be used. Use immediate-release formulations in scenarios requiring rapid onset of action Label,21. The extended-release form is taken to decrease the incidence of mortality and myocardial infarction (MI) for individuals diagnosed with chronic coronary artery disease (CAD), including patients with previous myocardial infarction (MI) or unstable angina or with chronic stable angina. Additionally, the extended-release form is used to decrease the risk of death and recurrent episodes of stroke in patients with a history of stroke or TIA 21.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Effects on pain and fever

Acetylsalicylic acid disrupts the production of prostaglandins throughout the body by targeting cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) 9,10,11. Prostaglandins are potent, irritating substances that have been shown to cause headaches and pain upon injection into humans. Prostaglandins increase the sensitivity of pain receptors and substances such as histamine and bradykinin. Through the disruption of the production and prevention of release of prostaglandins in inflammation, this drug may stop their action at pain receptors, preventing symptoms of pain. Acetylsalicylic acid is considered an antipyretic agent because of its ability to interfere with the production of brain prostaglandin E1. Prostaglandin E1 is known to be an extremely powerful fever-inducing agent Label.

Effects on platelet aggregation

The inhibition of platelet aggregation by ASA occurs because of its interference with thromboxane A2 in platelets, caused by COX-1 inhibition. Thromboxane A2 is an important lipid responsible for platelet aggregation, which can lead to clot formation and future risk of heart attack or stroke Label.

A note on cancer prevention

ASA has been studied in recent years to determine its effect on the prevention of various malignancies 15. In general, acetylsalicylic acid is involved in the interference of various cancer signaling pathways, sometimes inducing or upregulating tumor suppressor genes 15,17. Results of various studies suggest that there are beneficial effects of long-term ASA use in the prevention of several types of cancer, including stomach, colorectal, pancreatic, and liver cancers 16. Research is ongoing.

Mechanism of action

Acetylsalicylic acid (ASA) blocks prostaglandin synthesis. It is non-selective for COX-1 and COX-2 enzymes 9,10,11. Inhibition of COX-1 results in the inhibition of platelet aggregation for about 7-10 days (average platelet lifespan). The acetyl group of acetylsalicylic acid binds with a serine residue of the cyclooxygenase-1 (COX-1) enzyme, leading to irreversible inhibition. This prevents the production of pain-causing prostaglandins. This process also stops the conversion of arachidonic acid to thromboxane A2 (TXA2), which is a potent inducer of platelet aggregation Label. Platelet aggregation can result in clots and harmful venous and arterial thromboembolism, leading to conditions such as pulmonary embolism and stroke.

It is important to note that there is 60% homology between the protein structures of COX-1 and COX-2. ASA binds to serine 516 residue on the active site of COX-2 in the same fashion as its binding to the serine 530 residue located on the active site of COX-1. The active site of COX-2 is, however, slightly larger than the active site of COX-1, so that arachidonic acid (which later becomes prostaglandins) manages to bypass the aspirin molecule inactivating COX-2 11,12. ASA, therefore, exerts more action on the COX-1 receptor rather than on the COX-2 receptor 14. A higher dose of acetylsalicylic acid is required for COX-2 inhibition 15.

TargetActionsOrganism
AProstaglandin G/H synthase 1
inhibitor
Humans
AProstaglandin G/H synthase 2
inhibitor
Humans
UAldo-keto reductase family 1 member C1
inhibitor
Humans
U5'-AMP-activated protein kinase
activator
Humans
UEndothelin-1 receptor
inhibitor
Humans
UCellular tumor antigen p53
inducer
acetylation
Humans
U78 kDa glucose-regulated protein
binding
Humans
URibosomal protein S6 kinase alpha-3
inhibitor
Humans
UNF-kappa-B inhibitor alpha
inhibitor
Humans
UTumor necrosis factor-inducible gene 6 protein
inhibitor
downregulator
Humans
UCaspase-1
inhibitor
downregulator
Humans
UCaspase-3
inhibitor
downregulator
Humans
UInhibitor of nuclear factor kappa-B kinase subunit betaNot AvailableHumans
UExtracellular signal-regulated kinase (ERK)Not AvailableHumans
UG1/S-specific cyclin-D1
downregulator
Humans
UMyc proto-oncogene protein
downregulator
Humans
UProliferating cell nuclear antigen
downregulator
Humans
UCyclin A
downregulator
Absorption

Absorption is generally rapid and complete following oral administration but absorption may be variable depending on the route, dosage form, and other factors including but not limited to the rate of tablet dissolution, gastric contents, gastric emptying time, and gastric pH Label.

Detailed absorption information

When ingested orally, acetylsalicylic acid is rapidly absorbed in both the stomach and proximal small intestine. The non-ionized acetylsalicylic acid passes through the stomach lining by passive diffusion. Ideal absorption of salicylate in the stomach occurs in the pH range of 2.15 - 4.10. Intestinal absorption of acetylsalicylic acid occurs at a much faster rate. At least half of the ingested dose is hydrolyzed to salicylic acid in the first-hour post-ingestion by esterases found in the gastrointestinal tract. Peak plasma salicylate concentrations occur between 1-2 hours post-administration Label.

Volume of distribution

This drug is distributed to body tissues shortly after administration. It is known to cross the placenta. The plasma contains high levels of salicylate, as well as tissues such as spinal, peritoneal and synovial fluids, saliva and milk. The kidney, liver, heart, and lungs are also found to be rich in salicylate concentration after dosing. Low concentrations of salicylate are usually low, and minimal concentrations are found in feces, bile, and sweat Label.

Protein binding

50% to 90% of a normal therapeutic concentration salicylate (a main metabolite of acetylsalicylic acid Label) binds plasma proteins, particularly albumin, while acetylsalicylic acid itself binds negligibly Label. Acetylsalicylic acid has the ability to bind to and acetylate many proteins, hormones, DNA, platelets, and hemoglobin Label.

Metabolism

Acetylsalicylic acid is hydrolyzed in the plasma to salicylic acid. Plasma concentrations of aspirin following after administration of the extended-release form are mostly undetectable 4-8 hours after ingestion of a single dose. Salicylic acid was measured at 24 hours following a single dose of extended-release acetylsalicylic acid 21.

Salicylate is mainly metabolized in the liver, although other tissues may also be involved in this process Label. The major metabolites of acetylsalicylic acid are salicylic acid, salicyluric acid, the ether or phenolic glucuronide and the ester or acyl glucuronide. A small portion is converted to gentisic acid and other hydroxybenzoic acids Label.

Hover over products below to view reaction partners

Route of elimination

Excretion of salicylates occurs mainly through the kidney, by the processes of glomerular filtration and tubular excretion, in the form of free salicylic acid, salicyluric acid, and, additionally, phenolic and acyl glucuronides Label.

Salicylate can be found in the urine soon after administration, however, the entire dose takes about 48 hours to be completely eliminated. The rate of salicylate is often variable, ranging from 10% to 85% in the urine, and heavily depends on urinary pH. Acidic urine generally aids in reabsorption of salicylate by the renal tubules, while alkaline urine increases excretion Label.

After the administration of a typical 325mg dose, the elimination of ASA is found to follow first order kinetics in a linear fashion. At high concentrations, the elimination half-life increases Label.

Half-life

The half-life of ASA in the circulation ranges from 13 - 19 minutes. Blood concentrations drop rapidly after complete absorption. The half-life of the salicylate ranges between 3.5 and 4.5 hours Label.

Clearance

The clearance rate of acetylsalicylic acid is extremely variable, depending on several factors 6. Dosage adjustments may be required in patients with renal impairment Label. The extended-release tablet should not be administered to patients with eGFR of less than 10 mL/min 21.

Adverse Effects
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Toxicity

Lethal doses

Acute oral LD50 values have been reported as over 1.0 g/kg in humans, cats, and dogs, 0.92 g/kg - 1.48 g/kg in albino rats, 1.19 g/kg in guinea pigs, 1.1 g/kg in mice, and 1.8 g/kg in rabbit models Label.

Acute toxicity

Salicylate toxicity is a problem that may develop with both acute and chronic salicylate exposure 7. Multiple organ systems may be affected by salicylate toxicity, including the central nervous system, the pulmonary system, and the gastrointestinal system. Severe bleeding may occur. In the majority of cases, patients suffering from salicylate toxicity are volume-depleted at the time of presentation for medical attention. Fluid resuscitation should occur immediately and volume status should be monitored closely. Disruptions in acid-base balance are frequent in ASA toxicity 7.

The acute toxicity of acetylsalicylic in animals has been widely studied. The signs of poisoning in rats from lethal doses are mild to severe gastroenteritis, hepatitis, nephritis, pulmonary edema, encephalopathy, shock and some toxic effects on other organs and tissues. Mortality has been observed following convulsions or cardiovascular shock. An important differentiating property between various animal species is the ability to vomit toxic doses. Humans, cats and dogs have this ability, but rodents or rabbits do not Label.

Chronic toxicity and carcinogenesis

Chronic ASA toxicity is frequently accompanied by atypical clinical presentations that may be similar to diabetic ketoacidosis, delirium, cerebrovascular accident (CVA), myocardial infarction (MI) or cardiac failure. Plasma salicylate concentrations should be measured if salicylate intoxication is suspected, even if there no documentation available to suggest ASA was ingested. In older age, nephrotoxicity from salicylates increases, and the risk of upper gastrointestinal hemorrhage is increased, with higher rates of mortality 8. It is also important to note that ASA toxicity may occur even with close to normal serum concentrations. Prevention of chronic ASA includes the administration of smallest possible doses, avoidance of concurrent use of salicylate drugs, and therapeutic drug monitoring. Renal function should be regularly monitored and screening for gastrointestinal bleeding should be done at regular intervals 8.

Chronic toxicity studies were performed in rodents. ASA was administered at doses measured to be 2 to 20 times the maximum tolerated clinical dose to mice for up to one year. Negative dose-related effects were seen. These include decreased mean survival time, decreased number of births and progeny reaching an appropriate age for weaning. No evidence of carcinogenesis was found in 1-year studies Label. At daily doses of 0.24 g/kg/day given for 100 days to albino rats, ASA led to signs to excessive thirst, aciduria, diuresis, drowsiness, hyperreflexia, piloerection, changes in respiration, tachycardia, followed by soft stools, epistaxis, sialorrhea, dacryorrhea and mortality during hypothermic coma in the second study month Label.

Use in pregnancy and lactation

While teratogenic effects were observed in animals nearly lethal doses, no evidence suggests that this drug is teratogenic in humans Label. It is advisable, however, to avoid ASA use the first and second trimester of pregnancy, unless it is clearly required. If acetylsalicylic acid containing drugs are ingested by a patient attempting to conceive, or during the first and second trimester of pregnancy, the lowest possible dose at the shortest possible duration should be taken Label. This drug is contraindicated in the 3rd trimester of pregnancy Label.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Acetylsalicylic Acid Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of acetylsalicylic acid.Details
Leukotriene C4 synthase---(A;C) / (C;C)C alleleADR Directly StudiedThe presence of this genotype in LTC4S may indicate an increased risk of chronic urticaria when treated with acetylsalicylic acid.Details
Integrin beta-3GPIIIa PlA2(C;C) / (C;T)T > CEffect Directly StudiedPatients with this genotype have increased resistance to the anti-thrombotic effects of aspirin.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAcetylsalicylic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe metabolism of Acetylsalicylic acid can be increased when combined with Abatacept.
AbciximabAcetylsalicylic acid may increase the antiplatelet activities of Abciximab.
AbirateroneThe metabolism of Acetylsalicylic acid can be decreased when combined with Abiraterone.
AcarboseThe risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Acarbose.
AcebutololAcetylsalicylic acid may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Acetylsalicylic acid.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Acemetacin is combined with Acetylsalicylic acid.
AcenocoumarolAcetylsalicylic acid may increase the anticoagulant activities of Acenocoumarol.
AcetazolamideAcetylsalicylic acid may decrease the excretion rate of Acetazolamide which could result in a higher serum level.
Additional Data Available
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    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol. Alcohol increases the risk of gastrointestinal bleeding.
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
  • Take after a meal. This reduces irritating gastrointestinal effects.
  • Take with a full glass of water.

Products

Product Images
International/Other Brands
Acenterine / Acetophen (Merck) / Adiro / Aspergum / Aspro / Easprin / Empirin / Nu-seals / Rhodine / Rhonal / Solprin / Solprin acid / St. Joseph Aspirin for Adults / Tasprin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DurlazaCapsule, extended release162.5 mg/1OralNew Haven Pharmaceuticals, Inc.2015-09-25Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
365 Everyday Value AspirinTablet, film coated325 mg/1OralWhole Foods Market, Inc.2018-08-23Not applicableUS flag
7 Select Adult Chewable AspirinTablet, chewable81 mg/1Oral7 Eleven2014-08-052017-08-09US flag
7 Select AspirinTablet, film coated325 mg/1Oral7-Eleven2014-08-052021-03-31US flag
81 mg Low Dose AspirinTablet81 mg/1OralBig Lots Stores, Inc.2008-02-122013-06-25US flag
A.S.A.TabletOralD.C. Labs Limited2001-05-282005-07-19Canada flag
A.S.A.TabletOralD.C. Labs Limited2001-12-222005-07-19Canada flag
A.S.A. (acetylsalicylic Acid) Tab 325mg USPTabletOralAccurex Health Care Manufacturing Inc.1996-12-312003-01-28Canada flag
A.S.A. 325 Mg TabletTabletOralJamp Pharma Corporation2003-10-16Not applicableCanada flag
A.S.A. 80mg Acetylsalicylic Acid TabletsTabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1995-12-312002-07-31Canada flag
A.S.A. Enteric Coated Tab 325mgTablet, delayed releaseOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1987-12-312004-07-26Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
10 Person ANSIAcetylsalicylic acid (325 mg/1) + Acetaminophen (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ibuprofen (200 mg/1) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalGenuine First Aid2010-04-24Not applicableUS flag
217Acetylsalicylic acid (325 mg) + Caffeine citrate (30 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1910-12-311998-04-21Canada flag
217 Strong TabAcetylsalicylic acid (500 mg) + Caffeine citrate (30 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1973-12-311998-04-21Canada flag
222 TabletsAcetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) + Codeine phosphate (8 mg)TabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1951-12-312015-08-17Canada flag
25 Person ANSIAcetylsalicylic acid (325 mg/1) + Acetaminophen (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Ibuprofen (200 mg/1) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalGenuine First Aid2010-04-25Not applicableUS flag
282 Mep TabAcetylsalicylic acid (350 mg) + Caffeine citrate (30 mg) + Codeine phosphate (15 mg) + Meprobamate (200 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1959-12-311998-08-14Canada flag
282 TabAcetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) + Codeine phosphate (15 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-311998-04-21Canada flag
282 TabletsAcetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) + Codeine phosphate (15 mg)TabletOralPendopharm Division Of De Pharmascience Inc1998-11-01Not applicableCanada flag
292 TabAcetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) + Codeine phosphate (30 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-311998-08-14Canada flag
292 TabletsAcetylsalicylic acid (375 mg) + Caffeine citrate (30 mg) + Codeine phosphate (30 mg)TabletOralPendopharm Division Of De Pharmascience Inc1998-10-01Not applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4032 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4134 First Aid KitAcetylsalicylic acid (325 mg/1) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4139 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)KitOral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4142 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Lidocaine hydrochloride (2 g/100g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4154 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)KitOral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4196 First Aid KitAcetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4209 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzocaine (20 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4211 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzocaine (20 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4213 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Povidone-iodine (10 mg/1mL)KitOral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4214 First Aid KitAcetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzalkonium chloride (0.13 g/100mL) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag

Categories

ATC Codes
B01AC06 — Acetylsalicylic acidC07FX04 — Bisoprolol and acetylsalicylic acidC10BX04 — Simvastatin, acetylsalicylic acid and ramiprilM01BA03 — Acetylsalicylic acid and corticosteroidsN02BA71 — Acetylsalicylic acid, combinations with psycholepticsC10BX02 — Pravastatin and acetylsalicylic acidB01AC56 — Acetylsalicylic acid, combinations with proton pump inhibitorsN02AJ07 — Codeine and acetylsalicylic acidN02AJ02 — Dihydrocodeine and acetylsalicylic acidN02BA01 — Acetylsalicylic acidC10BX05 — Rosuvastatin and acetylsalicylic acidN02BA51 — Acetylsalicylic acid, combinations excl. psycholepticsA01AD05 — Acetylsalicylic acidC10BX01 — Simvastatin and acetylsalicylic acidC07FX03 — Metoprolol and acetylsalicylic acidN02AJ18 — Oxycodone and acetylsalicylic acidC10BX12 — Atorvastatin, acetylsalicylic acid and perindoprilC10BX08 — Atorvastatin and acetylsalicylic acidC10BX06 — Atorvastatin, acetylsalicylic acid and ramiprilC07FX02 — Sotalol and acetylsalicylic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Acylsalicylic acids
Alternative Parents
Phenol esters / Benzoic acids / Phenoxy compounds / Benzoyl derivatives / Dicarboxylic acids and derivatives / Carboxylic acid esters / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Acylsalicylic acid / Aromatic homomonocyclic compound / Benzoic acid / Benzoyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
salicylates, acetate ester, benzoic acids (CHEBI:15365)

Chemical Identifiers

UNII
R16CO5Y76E
CAS number
50-78-2
InChI Key
BSYNRYMUTXBXSQ-UHFFFAOYSA-N
InChI
InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
IUPAC Name
2-(acetyloxy)benzoic acid
SMILES
CC(=O)OC1=CC=CC=C1C(O)=O

References

Synthesis Reference

Marino Gobetti, Guido Vandoni, "Acetylsalicylic acid thioesters, a process for their preparation and pharmaceutical compositions containing them." U.S. Patent US4563443, issued March, 1981.

US4563443
General References
  1. Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. [PubMed:12411346]
  2. Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. [PubMed:11124191]
  3. Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. [PubMed:12484694]
  4. Authors unspecified: 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:2899772]
  5. 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:17456544]
  6. Levy G: Clinical pharmacokinetics of aspirin. Pediatrics. 1978 Nov;62(5 Pt 2 Suppl):867-72. [PubMed:724339]
  7. Authors unspecified: Guidance document: management priorities in salicylate toxicity. J Med Toxicol. 2015 Mar;11(1):149-52. doi: 10.1007/s13181-013-0362-3. [PubMed:25715929]
  8. Durnas C, Cusack BJ: Salicylate intoxication in the elderly. Recognition and recommendations on how to prevent it. Drugs Aging. 1992 Jan-Feb;2(1):20-34. [PubMed:1554971]
  9. Flower R: What are all the things that aspirin does? BMJ. 2003 Sep 13;327(7415):572-3. doi: 10.1136/bmj.327.7415.572. [PubMed:12969898]
  10. Hall MN, Campos H, Li H, Sesso HD, Stampfer MJ, Willett WC, Ma J: Blood levels of long-chain polyunsaturated fatty acids, aspirin, and the risk of colorectal cancer. Cancer Epidemiol Biomarkers Prev. 2007 Feb;16(2):314-21. [PubMed:17301265]
  11. Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [PubMed:14592543]
  12. Vane JR, Bakhle YS, Botting RM: Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol. 1998;38:97-120. doi: 10.1146/annurev.pharmtox.38.1.97. [PubMed:9597150]
  13. Varga Z, Sabzwari SRA, Vargova V: Cardiovascular Risk of Nonsteroidal Anti-Inflammatory Drugs: An Under-Recognized Public Health Issue. Cureus. 2017 Apr 8;9(4):e1144. doi: 10.7759/cureus.1144. [PubMed:28491485]
  14. Ornelas A, Zacharias-Millward N, Menter DG, Davis JS, Lichtenberger L, Hawke D, Hawk E, Vilar E, Bhattacharya P, Millward S: Beyond COX-1: the effects of aspirin on platelet biology and potential mechanisms of chemoprevention. Cancer Metastasis Rev. 2017 Jun;36(2):289-303. doi: 10.1007/s10555-017-9675-z. [PubMed:28762014]
  15. Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [PubMed:24874482]
  16. Tsoi KKF, Ho JMW, Chan FCH, Sung JJY: Long-term use of low-dose aspirin for cancer prevention: A 10-year population cohort study in Hong Kong. Int J Cancer. 2018 Dec 21. doi: 10.1002/ijc.32083. [PubMed:30575949]
  17. Li D, Wang P, Yu Y, Huang B, Zhang X, Xu C, Zhao X, Yin Z, He Z, Jin M, Liu C: Tumor-preventing activity of aspirin in multiple cancers based on bioinformatic analyses. PeerJ. 2018 Sep 26;6:e5667. doi: 10.7717/peerj.5667. eCollection 2018. [PubMed:30280037]
  18. Hasan Arif; Sandeep Aggarwal (2018). Salicylic Acid (Aspirin): StatPearls. StatPearls Publishing.
  19. Mayo Clinic website: Salicylate [Link]
  20. FDA Approved Products: Aspirin (acetylsalicylic acid) oral tablets [Link]
  21. Durlaza FDA label [File]
Human Metabolome Database
HMDB0001879
KEGG Drug
D00109
KEGG Compound
C01405
PubChem Compound
2244
PubChem Substance
46505803
ChemSpider
2157
BindingDB
22360
RxNav
1191
ChEBI
15365
ChEMBL
CHEMBL25
ZINC
ZINC000000000053
Therapeutic Targets Database
DAP000843
PharmGKB
PA448497
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
AIN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Aspirin
AHFS Codes
  • 28:08.04.24 — Salicylates
PDB Entries
1oxr / 1tgm / 2qqt / 3gcl / 3iaz / 4nsb / 6mqf
FDA label
Download (399 KB)
MSDS
Download (24.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic SciencePlatelet Function1
4Active Not RecruitingPreventionAspirin / Coronary Artery Disease (CAD)1
4Active Not RecruitingPreventionDiabetes Mellitus1
4Active Not RecruitingPreventionIntracranial Hemorrhages / Ischemia, Brain1
4Active Not RecruitingPreventionMalignancies1
4Active Not RecruitingTreatmentAcute Myocardial Infarction (AMI)1
4Active Not RecruitingTreatmentAtrial Fibrillation (AF) / Valve Heart Disease1
4Active Not RecruitingTreatmentCerebral Small Vessels Disease1
4Active Not RecruitingTreatmentCoronary Heart Disease (CHD)1
4Active Not RecruitingTreatmentCoronary Heart Disease (CHD) / Percutaneous Transluminal Coronary Angioplasty1

Pharmacoeconomics

Manufacturers
  • Bayer healthcare llc
Packagers
  • 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.
Dosage Forms
FormRouteStrength
TabletOral
KitOphthalmic; Oral; Respiratory (inhalation); Topical
KitOral; Respiratory (inhalation); Topical
TabletOral100 mg
Kit; tablet, delayed release; tablet, extended releaseOral
Tablet, delayed releaseOral81 mg/1
TabletOral325 1/1
KitOral; Topical
KitTopical
TabletOral200 mg
Capsule, extended releaseOral
Tablet, effervescentOral324 mg
Granule, effervescentOral
Tablet, effervescentOral
Capsule, coated pellets160 mg
SuppositoryRectal
Tablet, chewableOral
Tablet, film coatedOral500 mg/1
Tablet, effervescentOral10 mg
Tablet, effervescentOral20 mg
Gum, chewingOral
SuppositoryRectal300 mg/1
SuppositoryRectal600 mg/1
TabletOral325 g/1
TabletOral325 mg/1
Tablet, coatedOral325 ng/1
Tablet, coatedOral325 mg/1
Tablet, extended releaseOral81 mg/1
Tablet, film coatedOral325 mg/1
Tablet0.5 g
Tablet, coatedOral500 MG
Tablet, delayed release; tablet, extended releaseOral
PowderOral500 mg
Tablet, delayed releaseOral81 mg/811
Tablet, chewableOral500 mg
Tablet, coatedOral81 mg/1
GranuleOral
TabletOral500 mg
Tablet, coatedOral500 mg/5001
TabletOral81 mg/1
Tablet, film coatedOral81 mg/1
Tablet, chewableOral81 mg/1
Tablet, effervescentOral500 mg
Tablet100 MG
Tablet, effervescentOral400 mg
Tablet, delayed releaseOral100 MG
Tablet, delayed releaseOral300 MG
Tablet0.1 g
PowderOral325 mg/1
Granule400 MG
Granule500 MG
Suppository1 G
Tablet400 MG
Tablet500 MG
Tablet, delayed releaseOral75 MG
Tablet75 MG
Tablet300 MG
Tablet, effervescentOral300 mg
Tablet80 mg
Tablet, coatedOral75 mg
Capsule10 mg
Capsule20 mg
TabletOral500 mg/1
PowderOral500 mg/1
Tablet, coatedOral500 mg/1
SprayOral6 mg/0.1mL
LozengeOral
Granule, effervescentOral0.65 g
Granule, effervescentOral0.5 g
TabletOral325 mg
CapsuleOral
TabletOral0.5 G
TabletOral324 MG
Tablet, delayed releaseOral81 mg
Powder, for solutionOral100 MG
Powder, for solutionOral160 MG
Powder, for solutionOral300 MG
Powder, for solutionOral75 MG
Tablet, effervescent500 mg
Tablet250 mg
Tablet, delayed release100 mg
Tablet, delayed release300 mg
TabletOral300 mg
Tablet500 mg/1
TabletOral250 mg
PasteDental
Tablet, film coatedOral
Capsule, extended releaseOral162.5 mg/1
Tablet, coatedOral150 mg
Tablet, delayed release150 mg
Tablet, delayed release500 mg
Tablet, delayed release81 mg
Capsule, coatedOral150 mg
Capsule, coatedOral300 mg
Capsule, coatedOral500 mg
Tablet, delayed releaseOral325 mg/3251
Tablet, delayed releaseOral
Capsule, gelatin coatedOral
Tablet, orally disintegratingOral81 mg/1
Tablet50 MG
KitOphthalmic; Oral; Topical
Capsule, coatedOral
Tablet, coatedOral162 mg/1621
Tablet, coatedOral81 mg/811
Tablet, film coatedTopical
PowderOral
CapsuleOral75 mg
Tablet, coatedOral
Tablet
Tablet, multilayerOral
Kit; tablet; tablet, delayed releaseOral
Tablet, effervescentOral200 mg
TabletOral
KitOral
Tablet
Tablet, delayed releaseOral325 mg/1
Tablet, coatedOral100 mg
Tablet, effervescent0.33 g
StripOral81 mg/1
Tablet, delayed releaseOral
TabletOral81 mg/81mg
TabletOral325 mg/325mg
Prices
Unit descriptionCostUnit
Entrophen 10 650 mg Enteric-Coated Tablet0.09USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5972916No1999-10-262017-07-14US flag
US6015577No2000-01-182017-01-18US flag
US6926907No2005-08-092023-02-28US flag
US9101637No2015-08-112022-03-23US flag
US9226892No2016-01-052032-09-29US flag
US8865187No2014-10-212022-03-23US flag
US9216150No2015-12-222032-09-29US flag
US9351984No2016-05-312021-12-19US flag
US9539214No2017-01-102033-03-13US flag
US9364439No2016-06-142022-05-31US flag
US8206741No2012-06-262023-02-28US flag
US9987231No2018-06-052033-01-02US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)138-140http://www.rsc.org/learn-chemistry/content/filerepository/CMP/00/000/045/Aspirin.pdf
boiling point (°C)140 °Chttp://www.chemicalland21.com/lifescience/phar/ACETYLSALICYLIC%20ACID.htm
water solubility10 mg/mLhttps://www.sigmaaldrich.com/catalog/product/sigma/a5376?lang=en®ion=US
logP1.18https://www.fip.org/files/fip/BPS/BCS/Monographs/AcetylsalicylicAcid.pdf
pKa3.5https://www.fip.org/files/fip/BPS/BCS/Monographs/AcetylsalicylicAcid.pdf
Predicted Properties
PropertyValueSource
Water Solubility1.46 mg/mLALOGPS
logP1.43ALOGPS
logP1.24ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.45 m3·mol-1ChemAxon
Polarizability17.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9645
Blood Brain Barrier+0.9376
Caco-2 permeable-0.6607
P-glycoprotein substrateNon-substrate0.685
P-glycoprotein inhibitor INon-inhibitor0.9118
P-glycoprotein inhibitor IINon-inhibitor0.9615
Renal organic cation transporterNon-inhibitor0.914
CYP450 2C9 substrateNon-substrate0.7518
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7225
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9576
CYP450 2C19 inhibitorNon-inhibitor0.9445
CYP450 3A4 inhibitorNon-inhibitor0.9611
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9557
Ames testNon AMES toxic0.9326
CarcinogenicityNon-carcinogens0.8356
BiodegradationReady biodegradable0.9067
Rat acute toxicity2.6386 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9433
hERG inhibition (predictor II)Non-inhibitor0.9799
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.27 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014l-2960000000-ffcb8d28ab7e460b0da8
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-006w-2910000000-910e8ce2493a05870b33
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00dl-9400000000-64327d3bef0063cf4fe1
GC-MS Spectrum - CI-BGC-MSsplash10-00di-0900000000-113943b65024522c1712
GC-MS Spectrum - EI-BGC-MSsplash10-014i-1590000000-7890c99ca2b0e2c4ff19
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014l-2960000000-ffcb8d28ab7e460b0da8
GC-MS Spectrum - GC-MSGC-MSsplash10-006w-2910000000-910e8ce2493a05870b33
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006w-2900000000-253eb678a85f77d4ba61
Mass Spectrum (Electron Ionization)MSsplash10-00dl-6900000000-74f8a29aa18d0c3afe98
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00kr-6900000000-324f46e8def1652ed4bf
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-cdf64eaf75083da6f355
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-ee75806b6fb8a38fd697
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-00dl-9400000000-64327d3bef0063cf4fe1
MS/MS Spectrum - CI-B (Unknown) , PositiveLC-MS/MSsplash10-00di-0900000000-113943b65024522c1712
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-1900000000-bc50013edb10656e0aa4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-2900000000-8c55c1f8d7cb7f247a5d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000l-9700000000-d475fd0478daf18a419a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9100000000-3daaf3c8697e17e67869
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9000000000-ee876bcdd1a5c7c229a0
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9000000000-cd4e1f8fe0a2bbc869f9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9000000000-4dca49851b5b9fd03d1a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00kf-9000000000-4611655c6aff89d706eb
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014l-9000000000-4d636e2d7318b857528d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ot-0900000000-1256ca04e4244fbc4a64
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ot-0900000000-2cae7e19320bfa1a03a0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ot-0900000000-42f69c49b256900b7524
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ot-0900000000-4860d5cbeeb9c31311ec
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006t-3900000000-cc185048e2a1bcc52124
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ba-9700000000-ec436cb71e803899f611
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9100000000-75f611f9e761b63033d9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-02tc-9000000000-15b9abe0f191aedd9620
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ik9-9000000000-644d508a79eb48c24ec3
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Flipo RM: [Are the NSAIDs able to compromising the cardio-preventive efficacy of aspirin?]. Presse Med. 2006 Sep;35(9 Spec No 1):1S53-60. [PubMed:17078596]
  2. Schwartz KA: Aspirin resistance: a review of diagnostic methodology, mechanisms, and clinical utility. Adv Clin Chem. 2006;42:81-110. [PubMed:17131625]
  3. Birnbaum Y, Ye Y, Lin Y, Freeberg SY, Huang MH, Perez-Polo JR, Uretsky BF: Aspirin augments 15-epi-lipoxin A4 production by lipopolysaccharide, but blocks the pioglitazone and atorvastatin induction of 15-epi-lipoxin A4 in the rat heart. Prostaglandins Other Lipid Mediat. 2007 Feb;83(1-2):89-98. Epub 2006 Nov 7. [PubMed:17259075]
  4. Guthikonda S, Lev EI, Patel R, DeLao T, Bergeron AL, Dong JF, Kleiman NS: Reticulated platelets and uninhibited COX-1 and COX-2 decrease the antiplatelet effects of aspirin. J Thromb Haemost. 2007 Mar;5(3):490-6. [PubMed:17319904]
  5. Durlaza FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Hall MN, Campos H, Li H, Sesso HD, Stampfer MJ, Willett WC, Ma J: Blood levels of long-chain polyunsaturated fatty acids, aspirin, and the risk of colorectal cancer. Cancer Epidemiol Biomarkers Prev. 2007 Feb;16(2):314-21. [PubMed:17301265]
  2. Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [PubMed:14592543]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
This is a potential target. Supporting data in the literature are limited.
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the in...
Gene Name
AKR1C1
Uniprot ID
Q04828
Uniprot Name
Aldo-keto reductase family 1 member C1
Molecular Weight
36788.02 Da
References
  1. Dhagat U, Carbone V, Chung RP, Matsunaga T, Endo S, Hara A, El-Kabbani O: A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase. Med Chem. 2007 Nov;3(6):546-50. [PubMed:18045204]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Tau-protein kinase activity
Specific Function
Catalytic subunit of AMP-activated protein kinase (AMPK), an energy sensor protein kinase that plays a key role in regulating cellular energy metabolism. In response to reduction of intracellular A...

Components:
References
  1. Din FV, Valanciute A, Houde VP, Zibrova D, Green KA, Sakamoto K, Alessi DR, Dunlop MG: Aspirin inhibits mTOR signaling, activates AMP-activated protein kinase, and induces autophagy in colorectal cancer cells. Gastroenterology. 2012 Jun;142(7):1504-15.e3. doi: 10.1053/j.gastro.2012.02.050. Epub 2012 Mar 6. [PubMed:22406476]
  2. Hawley SA, Fullerton MD, Ross FA, Schertzer JD, Chevtzoff C, Walker KJ, Peggie MW, Zibrova D, Green KA, Mustard KJ, Kemp BE, Sakamoto K, Steinberg GR, Hardie DG: The ancient drug salicylate directly activates AMP-activated protein kinase. Science. 2012 May 18;336(6083):918-22. doi: 10.1126/science.1215327. Epub 2012 Apr 19. [PubMed:22517326]
  3. Steinberg GR, Dandapani M, Hardie DG: AMPK: mediating the metabolic effects of salicylate-based drugs? Trends Endocrinol Metab. 2013 Oct;24(10):481-7. doi: 10.1016/j.tem.2013.06.002. Epub 2013 Jul 19. [PubMed:23871515]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
Receptor for endothelin-1. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of binding affinities for ET-A is:...
Gene Name
EDNRA
Uniprot ID
P25101
Uniprot Name
Endothelin-1 receptor
Molecular Weight
48721.76 Da
References
  1. Talbodec A, Berkane N, Blandin V, Breittmayer JP, Ferrari E, Frelin C, Vigne P: Aspirin and sodium salicylate inhibit endothelin ETA receptors by an allosteric type of mechanism. Mol Pharmacol. 2000 Apr;57(4):797-804. [PubMed:10727528]
  2. Blandin V, Vigne P, Breittmayer JP, Frelin C: Allosteric inhibition of endothelin ETA receptors by 3, 5-dibromosalicylic acid. Mol Pharmacol. 2000 Dec;58(6):1461-9. [PubMed:11093786]
  3. Davenport AP, Hyndman KA, Dhaun N, Southan C, Kohan DE, Pollock JS, Pollock DM, Webb DJ, Maguire JJ: Endothelin. Pharmacol Rev. 2016 Apr;68(2):357-418. doi: 10.1124/pr.115.011833. [PubMed:26956245]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Acetylation
General Function
Not Available
Specific Function
Not Available
Gene Name
TP53
Uniprot ID
P04637
Uniprot Name
Cellular tumor antigen p53
Molecular Weight
43652.79 Da
References
  1. Alfonso LF, Srivenugopal KS, Bhat GJ: Does aspirin acetylate multiple cellular proteins? (Review). Mol Med Rep. 2009 Jul-Aug;2(4):533-7. doi: 10.3892/mmr_00000132. [PubMed:21475861]
  2. Ai G, Dachineni R, Kumar DR, Marimuthu S, Alfonso LF, Bhat GJ: Aspirin acetylates wild type and mutant p53 in colon cancer cells: identification of aspirin acetylated sites on recombinant p53. Tumour Biol. 2016 May;37(5):6007-16. doi: 10.1007/s13277-015-4438-3. Epub 2015 Nov 23. [PubMed:26596838]
  3. Su YF, Yang SH, Lee YH, Wu BC, Huang SC, Liu CM, Chen SL, Pan YF, Chou SS, Chou MY, Yang HW: Aspirin-induced inhibition of adipogenesis was p53-dependent and associated with inactivation of pentose phosphate pathway. Eur J Pharmacol. 2014 Sep 5;738:101-10. doi: 10.1016/j.ejphar.2014.03.009. Epub 2014 Apr 12. [PubMed:24726874]
  4. Ranganathan S, Joseph J, Mehta JL: Aspirin inhibits human coronary artery endothelial cell proliferation by upregulation of p53. Biochem Biophys Res Commun. 2003 Jan 31;301(1):143-6. [PubMed:12535653]
  5. Luciani MG, Campregher C, Gasche C: Aspirin blocks proliferation in colon cells by inducing a G1 arrest and apoptosis through activation of the checkpoint kinase ATM. Carcinogenesis. 2007 Oct;28(10):2207-17. doi: 10.1093/carcin/bgm101. Epub 2007 May 17. [PubMed:17510082]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binding
Curator comments
Data regarding this target in relation to acetylsalicylic acid are limited in the literature.
General Function
Unfolded protein binding
Specific Function
Probably plays a role in facilitating the assembly of multimeric protein complexes inside the endoplasmic reticulum. Involved in the correct folding of proteins and degradation of misfolded protein...
Gene Name
HSPA5
Uniprot ID
P11021
Uniprot Name
78 kDa glucose-regulated protein
Molecular Weight
72332.425 Da
References
  1. Deng WG, Ruan KH, Du M, Saunders MA, Wu KK: Aspirin and salicylate bind to immunoglobulin heavy chain binding protein (BiP) and inhibit its ATPase activity in human fibroblasts. FASEB J. 2001 Nov;15(13):2463-70. [PubMed:11689471]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Ribosomal protein s6 kinase activity
Specific Function
Serine/threonine-protein kinase that acts downstream of ERK (MAPK1/ERK2 and MAPK3/ERK1) signaling and mediates mitogenic and stress-induced activation of the transcription factors CREB1, ETV1/ER81 ...
Gene Name
RPS6KA3
Uniprot ID
P51812
Uniprot Name
Ribosomal protein S6 kinase alpha-3
Molecular Weight
83735.325 Da
References
  1. Stevenson MA, Zhao MJ, Asea A, Coleman CN, Calderwood SK: Salicylic acid and aspirin inhibit the activity of RSK2 kinase and repress RSK2-dependent transcription of cyclic AMP response element binding protein- and NF-kappa B-responsive genes. J Immunol. 1999 Nov 15;163(10):5608-16. [PubMed:10553090]
  2. Stratford AL, Dunn SE: The promise and challenges of targeting RSK for the treatment of cancer. Expert Opin Ther Targets. 2011 Jan;15(1):1-4. doi: 10.1517/14728222.2011.537656. [PubMed:21142801]
  3. O'Neill EA: A new target for aspirin. Nature. 1998 Nov 5;396(6706):15, 17. doi: 10.1038/23810. [PubMed:9817196]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data in the literature are limited regarding this target action.
General Function
Ubiquitin protein ligase binding
Specific Function
Inhibits the activity of dimeric NF-kappa-B/REL complexes by trapping REL dimers in the cytoplasm through masking of their nuclear localization signals. On cellular stimulation by immune and proinf...
Gene Name
NFKBIA
Uniprot ID
P25963
Uniprot Name
NF-kappa-B inhibitor alpha
Molecular Weight
35608.65 Da
References
  1. Stevenson MA, Zhao MJ, Asea A, Coleman CN, Calderwood SK: Salicylic acid and aspirin inhibit the activity of RSK2 kinase and repress RSK2-dependent transcription of cyclic AMP response element binding protein- and NF-kappa B-responsive genes. J Immunol. 1999 Nov 15;163(10):5608-16. [PubMed:10553090]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
General Function
Hyaluronic acid binding
Specific Function
Possibly involved in cell-cell and cell-matrix interactions during inflammation and tumorigenesis.
Gene Name
TNFAIP6
Uniprot ID
P98066
Uniprot Name
Tumor necrosis factor-inducible gene 6 protein
Molecular Weight
31203.09 Da
References
  1. Shackelford RE, Alford PB, Xue Y, Thai SF, Adams DO, Pizzo S: Aspirin inhibits tumor necrosis factoralpha gene expression in murine tissue macrophages. Mol Pharmacol. 1997 Sep;52(3):421-9. [PubMed:9281604]
  2. Jiang DQ, Liu H, Zhang SB, Zhang XL: Aspirin inhibits tumor necrosis factor-alpha-stimulated fractalkine expression in human umbilical vein endothelial cells. Chin Med J (Engl). 2009 May 20;122(10):1147-53. [PubMed:19493461]
  3. Kim J, Lee KS, Kim JH, Lee DK, Park M, Choi S, Park W, Kim S, Choi YK, Hwang JY, Choe J, Won MH, Jeoung D, Lee H, Ryoo S, Ha KS, Kwon YG, Kim YM: Aspirin prevents TNF-alpha-induced endothelial cell dysfunction by regulating the NF-kappaB-dependent miR-155/eNOS pathway: Role of a miR-155/eNOS axis in preeclampsia. Free Radic Biol Med. 2017 Mar;104:185-198. doi: 10.1016/j.freeradbiomed.2017.01.010. Epub 2017 Jan 11. [PubMed:28087411]
  4. Kutuk O, Basaga H: Aspirin inhibits TNFalpha- and IL-1-induced NF-kappaB activation and sensitizes HeLa cells to apoptosis. Cytokine. 2004 Mar 7;25(5):229-37. doi: 10.1016/j.cyto.2003.11.007. [PubMed:15036249]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
General Function
Endopeptidase activity
Specific Function
Thiol protease that cleaves IL-1 beta between an Asp and an Ala, releasing the mature cytokine which is involved in a variety of inflammatory processes. Important for defense against pathogens. Cle...
Gene Name
CASP1
Uniprot ID
P29466
Uniprot Name
Caspase-1
Molecular Weight
45158.215 Da
References
  1. Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [PubMed:24874482]
  2. Pathi S, Jutooru I, Chadalapaka G, Nair V, Lee SO, Safe S: Aspirin inhibits colon cancer cell and tumor growth and downregulates specificity protein (Sp) transcription factors. PLoS One. 2012;7(10):e48208. doi: 10.1371/journal.pone.0048208. Epub 2012 Oct 26. [PubMed:23110215]
  3. Zhang H, Lu J, Jiao Y, Chen Q, Li M, Wang Z, Yu Z, Huang X, Yao A, Gao Q, Xie W, Li L, Yao P: Aspirin Inhibits Natural Killer/T-Cell Lymphoma by Modulation of VEGF Expression and Mitochondrial Function. Front Oncol. 2019 Jan 14;8:679. doi: 10.3389/fonc.2018.00679. eCollection 2018. [PubMed:30693272]
  4. Dhanoya T, Burn J: Colon cancer and Salicylates. Evol Med Public Health. 2016 Apr 15;2016(1):146-7. doi: 10.1093/emph/eow009. Print 2016. [PubMed:26980842]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
General Function
Phospholipase a2 activator activity
Specific Function
Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' ...
Gene Name
CASP3
Uniprot ID
P42574
Uniprot Name
Caspase-3
Molecular Weight
31607.58 Da
References
  1. Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [PubMed:24874482]
  2. Pathi S, Jutooru I, Chadalapaka G, Nair V, Lee SO, Safe S: Aspirin inhibits colon cancer cell and tumor growth and downregulates specificity protein (Sp) transcription factors. PLoS One. 2012;7(10):e48208. doi: 10.1371/journal.pone.0048208. Epub 2012 Oct 26. [PubMed:23110215]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Scaffold protein binding
Specific Function
Serine kinase that plays an essential role in the NF-kappa-B signaling pathway which is activated by multiple stimuli such as inflammatory cytokines, bacterial or viral products, DNA damages or oth...
Gene Name
IKBKB
Uniprot ID
O14920
Uniprot Name
Inhibitor of nuclear factor kappa-B kinase subunit beta
Molecular Weight
86563.245 Da
References
  1. Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [PubMed:24874482]
  2. Yamamoto Y, Yin MJ, Gaynor RB: IkappaB kinase alpha (IKKalpha) regulation of IKKbeta kinase activity. Mol Cell Biol. 2000 May;20(10):3655-66. [PubMed:10779355]
  3. Konig HG, Watters O, Kinsella S, Ameen M, Fenner BJ, Prehn JHM: A constitutively-active IKK-complex at the axon initial segment. Brain Res. 2018 Jan 1;1678:356-366. doi: 10.1016/j.brainres.2017.10.020. Epub 2017 Oct 24. [PubMed:29079505]
  4. Gamble C, McIntosh K, Scott R, Ho KH, Plevin R, Paul A: Inhibitory kappa B Kinases as targets for pharmacological regulation. Br J Pharmacol. 2012 Feb;165(4):802-19. doi: 10.1111/j.1476-5381.2011.01608.x. [PubMed:21797846]
  5. Yamamoto Y, Gaynor RB: Therapeutic potential of inhibition of the NF-kappaB pathway in the treatment of inflammation and cancer. J Clin Invest. 2001 Jan;107(2):135-42. doi: 10.1172/JCI11914. [PubMed:11160126]
  6. Rohl M, Pasparakis M, Baudler S, Baumgartl J, Gautam D, Huth M, De Lorenzi R, Krone W, Rajewsky K, Bruning JC: Conditional disruption of IkappaB kinase 2 fails to prevent obesity-induced insulin resistance. J Clin Invest. 2004 Feb;113(3):474-81. doi: 10.1172/JCI18712. [PubMed:14755344]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
General Function
Rna polymerase ii carboxy-terminal domain kinase activity
Specific Function
Serine/threonine kinase which acts as an essential component of the MAP kinase signal transduction pathway. MAPK1/ERK2 and MAPK3/ERK1 are the 2 MAPKs which play an important role in the MAPK/ERK ca...

Components:
References
  1. Alfonso L, Ai G, Spitale RC, Bhat GJ: Molecular targets of aspirin and cancer prevention. Br J Cancer. 2014 Jul 8;111(1):61-7. doi: 10.1038/bjc.2014.271. Epub 2014 May 29. [PubMed:24874482]
  2. Wang L, Wu J, Zhang W, Zhi Y, Wu Y, Jiang R, Yang R: Effects of aspirin on the ERK and PI3K/Akt signaling pathways in rats with acute pulmonary embolism. Mol Med Rep. 2013 Nov;8(5):1465-71. doi: 10.3892/mmr.2013.1676. Epub 2013 Sep 10. [PubMed:24026640]
  3. Nishio T, Usami M, Awaji M, Shinohara S, Sato K: Dual effects of acetylsalicylic acid on ERK signaling and Mitf transcription lead to inhibition of melanogenesis. Mol Cell Biochem. 2016 Jan;412(1-2):101-10. doi: 10.1007/s11010-015-2613-x. Epub 2015 Dec 23. [PubMed:26699907]
  4. Weissmann G, Montesinos MC, Pillinger M, Cronstein BN: Non-prostaglandin effects of aspirin III and salicylate: inhibition of integrin-dependent human neutrophil aggregation and inflammation in COX 2- and NF kappa B (P105)-knockout mice. Adv Exp Med Biol. 2002;507:571-7. [PubMed:12664642]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Transcription factor binding
Specific Function
Regulatory component of the cyclin D1-CDK4 (DC) complex that phosphorylates and inhibits members of the retinoblastoma (RB) protein family including RB1 and regulates the cell-cycle during G(1)/S t...
Gene Name
CCND1
Uniprot ID
P24385
Uniprot Name
G1/S-specific cyclin-D1
Molecular Weight
33728.74 Da
References
  1. Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [PubMed:10993886]
  2. Cheng R, Liu YJ, Cui JW, Yang M, Liu XL, Li P, Wang Z, Zhu LZ, Lu SY, Zou L, Wu XQ, Li YX, Zhou Y, Fang ZY, Wei W: Aspirin regulation of c-myc and cyclinD1 proteins to overcome tamoxifen resistance in estrogen receptor-positive breast cancer cells. Oncotarget. 2017 May 2;8(18):30252-30264. doi: 10.18632/oncotarget.16325. [PubMed:28415819]
  3. Fan W, Li J, Chen J, Zhu L, Wang Y, Sun B, Hua B, Guo C, Yan Z: Aspirin inhibits the proliferation of synovium-derived mesenchymal stem cells by arresting the cell cycle in the G0/G1 phase. Am J Transl Res. 2017 Nov 15;9(11):5056-5062. eCollection 2017. [PubMed:29218104]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
Transcription factor that binds DNA in a non-specific manner, yet also specifically recognizes the core sequence 5'-CAC[GA]TG-3'. Activates the transcription of growth-related genes.
Gene Name
MYC
Uniprot ID
P01106
Uniprot Name
Myc proto-oncogene protein
Molecular Weight
48803.55 Da
References
  1. Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [PubMed:10993886]
  2. Cheng R, Liu YJ, Cui JW, Yang M, Liu XL, Li P, Wang Z, Zhu LZ, Lu SY, Zou L, Wu XQ, Li YX, Zhou Y, Fang ZY, Wei W: Aspirin regulation of c-myc and cyclinD1 proteins to overcome tamoxifen resistance in estrogen receptor-positive breast cancer cells. Oncotarget. 2017 May 2;8(18):30252-30264. doi: 10.18632/oncotarget.16325. [PubMed:28415819]
  3. Ai G, Dachineni R, Muley P, Tummala H, Bhat GJ: Aspirin and salicylic acid decrease c-Myc expression in cancer cells: a potential role in chemoprevention. Tumour Biol. 2016 Feb;37(2):1727-38. doi: 10.1007/s13277-015-3959-0. Epub 2015 Aug 28. [PubMed:26314861]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Auxiliary protein of DNA polymerase delta and is involved in the control of eukaryotic DNA replication by increasing the polymerase's processibility during elongation of the leading strand. Induces a robust stimulatory effect on the 3'-5' exonuclease and 3'-phosphodiesterase, but not apurinic-apyrimidinic (AP) endonuclease, APEX2 activities. Has to be loaded onto DNA in order to be able to stimulate APEX2. Plays a key role in DNA damage response (DDR) by being conveniently positioned at the replication fork to coordinate DNA replication with DNA repair and DNA damage tolerance pathways (PubMed:24939902). Acts as a loading platform to recruit DDR proteins that allow completion of DNA replication after DNA damage and promote postreplication repair: Monoubiquitinated PCNA leads to recruitment of translesion (TLS) polymerases, while 'Lys-63'-linked polyubiquitination of PCNA is involved in error-free pathway and employs recombination mechanisms to synthesize across the lesion.
Specific Function
Chromatin binding
Gene Name
PCNA
Uniprot ID
P12004
Uniprot Name
Proliferating cell nuclear antigen
Molecular Weight
28768.48 Da
References
  1. Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [PubMed:10993886]
  2. Krishnan K, Aoki T, Ruffin MT, Normolle DP, Boland CR, Brenner DE: Effects of low dose aspirin (81 mg) on proliferating cell nuclear antigen and Amaranthus caudatus labeling in normal-risk and high-risk human subjects for colorectal cancer. Cancer Detect Prev. 2004;28(2):107-13. doi: 10.1016/j.cdp.2004.01.001. [PubMed:15068834]
  3. Din FV, Valanciute A, Houde VP, Zibrova D, Green KA, Sakamoto K, Alessi DR, Dunlop MG: Aspirin inhibits mTOR signaling, activates AMP-activated protein kinase, and induces autophagy in colorectal cancer cells. Gastroenterology. 2012 Jun;142(7):1504-15.e3. doi: 10.1053/j.gastro.2012.02.050. Epub 2012 Mar 6. [PubMed:22406476]
18. Cyclin A
Kind
Group
Organism
Not Available
Pharmacological action
Unknown
Actions
Downregulator
References
  1. Law BK, Waltner-Law ME, Entingh AJ, Chytil A, Aakre ME, Norgaard P, Moses HL: Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen. J Biol Chem. 2000 Dec 8;275(49):38261-7. doi: 10.1074/jbc.M005545200. [PubMed:10993886]
  2. Dachineni R, Ai G, Kumar DR, Sadhu SS, Tummala H, Bhat GJ: Cyclin A2 and CDK2 as Novel Targets of Aspirin and Salicylic Acid: A Potential Role in Cancer Prevention. Mol Cancer Res. 2016 Mar;14(3):241-52. doi: 10.1158/1541-7786.MCR-15-0360. Epub 2015 Dec 18. [PubMed:26685215]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
Data found in the literature regarding this enzyme action are currently limited to the results of one study.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Chen XP, Tan ZR, Huang SL, Huang Z, Ou-Yang DS, Zhou HH: Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects. Clin Pharmacol Ther. 2003 Mar;73(3):264-71. doi: 10.1067/mcp.2003.14. [PubMed:12621391]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Palikhe NS, Kim SH, Nam YH, Ye YM, Park HS: Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6. doi: 10.4168/aair.2011.3.4.273. Epub 2011 Jul 1. [PubMed:21966608]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
Gene Name
UGT1A6
Uniprot ID
P19224
Uniprot Name
UDP-glucuronosyltransferase 1-6
Molecular Weight
60750.215 Da
References
  1. Palikhe NS, Kim SH, Nam YH, Ye YM, Park HS: Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6. doi: 10.4168/aair.2011.3.4.273. Epub 2011 Jul 1. [PubMed:21966608]
  2. Chan AT, Tranah GJ, Giovannucci EL, Hunter DJ, Fuchs CS: Genetic variants in the UGT1A6 enzyme, aspirin use, and the risk of colorectal adenoma. J Natl Cancer Inst. 2005 Mar 16;97(6):457-60. doi: 10.1093/jnci/dji066. [PubMed:15770010]
  3. Chen Y, Kuehl GE, Bigler J, Rimorin CF, Schwarz Y, Shen DD, Lampe JW: UGT1A6 polymorphism and salicylic acid glucuronidation following aspirin. Pharmacogenet Genomics. 2007 Aug;17(8):571-9. doi: 10.1097/01.fpc.0000236339.79916.07. [PubMed:17622933]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Arylamine n-acetyltransferase activity
Specific Function
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name
NAT2
Uniprot ID
P11245
Uniprot Name
Arylamine N-acetyltransferase 2
Molecular Weight
33542.235 Da
References
  1. Palikhe NS, Kim SH, Nam YH, Ye YM, Park HS: Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6. doi: 10.4168/aair.2011.3.4.273. Epub 2011 Jul 1. [PubMed:21966608]
  2. McDonagh EM, Boukouvala S, Aklillu E, Hein DW, Altman RB, Klein TE: PharmGKB summary: very important pharmacogene information for N-acetyltransferase 2. Pharmacogenet Genomics. 2014 Aug;24(8):409-25. doi: 10.1097/FPC.0000000000000062. [PubMed:24892773]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563]
  2. Parvez MM, Shin HJ, Jung JA, Shin JG: Evaluation of para-Aminosalicylic Acid as a Substrate of Multiple Solute Carrier Uptake Transporters and Possible Drug Interactions with Nonsteroidal Anti-inflammatory Drugs In Vitro. Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: AAC.02392-16. doi: 10.1128/AAC.02392-16. Print 2017 May. [PubMed:28223391]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
Modulator
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186]
  2. Li MP, Tang J, Zhang ZL, Chen XP: Induction of both P-glycoprotein and specific cytochrome P450 by aspirin eventually does not alter the antithrombotic effect of clopidogrel. Clin Pharmacol Ther. 2015 Apr;97(4):324. doi: 10.1002/cpt.32. Epub 2014 Dec 15. [PubMed:25669934]
  3. Oh J, Shin D, Lim KS, Lee S, Jung KH, Chu K, Hong KS, Shin KH, Cho JY, Yoon SH, Ji SC, Yu KS, Lee H, Jang IJ: Aspirin decreases systemic exposure to clopidogrel through modulation of P-glycoprotein but does not alter its antithrombotic activity. Clin Pharmacol Ther. 2014 Jun;95(6):608-16. doi: 10.1038/clpt.2014.49. Epub 2014 Feb 24. [PubMed:24566733]
  4. Kugai M, Uchiyama K, Tsuji T, Yoriki H, Fukui A, Qin Y, Higashimura Y, Mizushima K, Yoshida N, Katada K, Kamada K, Handa O, Takagi T, Konishi H, Yagi N, Yoshikawa T, Shirasaka Y, Tamai I, Naito Y, Itoh Y: MDR1 is related to intestinal epithelial injury induced by acetylsalicylic acid. Cell Physiol Biochem. 2013;32(4):942-50. doi: 10.1159/000354497. Epub 2013 Oct 1. [PubMed:24107783]
  5. Flescher E, Rotem R, Kwon P, Azare J, Jaspers I, Cohen D: Aspirin enhances multidrug resistance gene 1 expression in human Molt-4 T lymphoma cells. Anticancer Res. 2000 Nov-Dec;20(6B):4441-4. [PubMed:11205285]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Parvez MM, Shin HJ, Jung JA, Shin JG: Evaluation of para-Aminosalicylic Acid as a Substrate of Multiple Solute Carrier Uptake Transporters and Possible Drug Interactions with Nonsteroidal Anti-inflammatory Drugs In Vitro. Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: AAC.02392-16. doi: 10.1128/AAC.02392-16. Print 2017 May. [PubMed:28223391]
  2. Wang C, Wang C, Liu Q, Meng Q, Cang J, Sun H, Peng J, Ma X, Huo X, Liu K: Aspirin and probenecid inhibit organic anion transporter 3-mediated renal uptake of cilostazol and probenecid induces metabolism of cilostazol in the rat. Drug Metab Dispos. 2014 Jun;42(6):996-1007. doi: 10.1124/dmd.113.055194. Epub 2014 Apr 1. [PubMed:24692216]

Drug created on June 13, 2005 07:24 / Updated on September 19, 2020 16:48

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