Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H8O4.C6H14N2O2 |
Molecular Weight | 326.345 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC[C@H](N)C(O)=O.CC(=O)OC1=C(C=CC=C1)C(O)=O
InChI
InChIKey=JJBCTCGUOQYZHK-ZSCHJXSPSA-N
InChI=1S/C9H8O4.C6H14N2O2/c1-6(10)13-8-5-3-2-4-7(8)9(11)12;7-4-2-1-3-5(8)6(9)10/h2-5H,1H3,(H,11,12);5H,1-4,7-8H2,(H,9,10)/t;5-/m.0/s1
Aspirin is a nonsteroidal anti-inflammatory drug. Aspirin is unique in this class of drugs because it irreversibly inhibits both COX-1 and COX-2 activity by acetylating a serine residue (Ser529 and Ser516, respectively) positioned in the arachidonic acid-binding channel, thus inhibiting the synthesis of prostaglandins and reducing the inflammatory response. The drug is used either alone or in combination with other compounds for the treatment of pain, headache, as well as for reducing the risk of stroke and heart attacks in patients with brain ischemia and cardiovascular diseases.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18543581
Curator's Comment: The penetration of the blood-brain barrier was studied in animals.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11124191
Curator's Comment: Felix Hoffmann discovered aspirin when working for Friedrich Bayer & Co. # Bayer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P23219|||Q5T7T7 Gene ID: 5742.0 Gene Symbol: PTGS1 Target Organism: Homo sapiens (Human) |
1.2 µM [IC50] | ||
Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) |
5.2 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SYNALGOS-DC Approved UseSYNALGOS-DC is a combination of dihydrocodeine, an opioid agonist, aspirin, a nonsteroidal anti-inflammatory drug, and caffeine, a methylxanthine, and is indicated for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. Launch Date1958 |
|||
Primary | FIORINAL Approved UseFIORINAL is indicated for the relief of the symptom complex of tension (or muscle contraction) headache. Evidence supporting the efficacy and safety of Fiorinal in the treatment of multiple recurrent headaches is unavailable. Caution in this regard is required because butalbital is habit-forming and potentially abusable. Launch Date1976 |
|||
Preventing | DURLAZA Approved UseDURLAZA is a nonsteroidal anti-inflammatory drug indicated to reduce the risk of death and myocardial infarction (MI) in patients with chronic coronary artery disease, such as patients with a history of MI or unstable angina pectoris or with chronic stable angina and to reduce the risk of death and recurrent stroke in patients who have had an ischemic stroke or transient ischemic attack. Launch Date2015 |
|||
Preventing | AGGRENOX Approved UseAGGRENOX is indicated to reduce the risk of stroke in patients who have had transient ischemia of the brain or completed ischemic stroke due to thrombosis. Launch Date1999 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54.25 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24672263 |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ASPIRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.84 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24672263 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
ASPIRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.31 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24672263 |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ASPIRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.12 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24672263 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
ASPIRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.322 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24672263 |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ASPIRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.422 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24672263 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
ASPIRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
68% |
ASPIRIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Sources: https://www.karger.com/Article/Abstract/321727 Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Sources: https://dmd.aspetjournals.org/content/42/6/996.short Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11205285/ Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
no | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
no | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
yes [Km 1242 uM] | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
yes [Km 2337 uM] | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
yes [Km 278.6 uM] | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
yes [Km 40.7 uM] | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
yes [Km 683.1 uM] | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
yes [Km 698.2 uM] | |||
Sources: https://dmd.aspetjournals.org/content/34/2/199.short Page: - |
yes [Km 94.2 uM] | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Severe gastrointestinal hemorrhage and anemia after therapeutic doses of aspirin in normal children. | 1976 Mar |
|
Iron deficiency anaemia and aspirin use in old age. | 1999 Sep |
|
Sleep attacks (sleep episodes) with pergolide. | 2000 Apr 15 |
|
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria. | 2000 Aug |
|
Pharmacotherapies for cocaine dependence. | 2000 Dec |
|
The discovery of aspirin: a reappraisal. | 2000 Dec 23-30 |
|
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. | 2000 Dec 8 |
|
[Cholestatic hepatitis as a rare side effect of therapy with ticlopidine]. | 2000 Jul |
|
Intermediate but not low doses of aspirin can suppress angiotensin-converting enzyme inhibitor-induced cough. | 2000 Jul |
|
An uncommon case of fluid retention simulating a congestive heart failure after aspirin consumption. | 2000 Jul |
|
Symptomatic secondary hemorrhagic transformation of ischemic Wallenberg's syndrome. | 2000 Jun |
|
Indications for early aspirin use in acute ischemic stroke : A combined analysis of 40 000 randomized patients from the chinese acute stroke trial and the international stroke trial. On behalf of the CAST and IST collaborative groups. | 2000 Jun |
|
Acetaminophen inhibits iNOS gene expression in RAW 264.7 macrophages: differential regulation of NF-kappaB by acetaminophen and salicylates. | 2000 Jun 16 |
|
Aspirin-associated intracerebral hemorrhage: clinical and radiologic features. | 2000 Jun 27 |
|
[Aspirin-induced angioedema of the nape of the neck with naproxen cross-reaction: a case report]. | 2000 May |
|
Clinical, biochemical, and genetic characterization of a novel estrogen-dependent inherited form of angioedema. | 2000 Sep |
|
The role of hydroxyl radical as a messenger in Cr(VI)-induced p53 activation. | 2000 Sep |
|
Aspirin induces apoptosis through mitochondrial cytochrome c release. | 2000 Sep 1 |
|
Novel platelet inhibitors. | 2001 |
|
Collagen as a model system to investigate the use of aspirin as an inhibitor of protein glycation and crosslinking. | 2001 Apr |
|
Cardiac risk factors, medication, and recurrent clinical events after acute coronary disease; a prospective cohort study. | 2001 Feb |
|
Non-steroidal anti-inflammatory drugs and gastrointestinal damage-problems and solutions. | 2001 Feb |
|
A novel synthetic inhibitor of factor Xa decreases early reocclusion and improves 24-h patency after coronary fibrinolysis in dogs. | 2001 Feb |
|
Risk factors for severe hemorrhagic transformation in ischemic stroke patients treated with recombinant tissue plasminogen activator: a secondary analysis of the European-Australasian Acute Stroke Study (ECASS II). | 2001 Feb |
|
Antiplatelet drugs for prevention of pre-eclampsia and its consequences: systematic review. | 2001 Feb 10 |
|
Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation. | 2001 Feb 10 |
|
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior. | 2001 Jan |
|
Present treatment options for unstable angina and non-Q-wave myocardial infarction. | 2001 Jan |
|
Antithrombotic agents in coronary artery disease. | 2001 Jan |
|
Gastric mucosal resistance to acute injury in experimental portal hypertension. | 2001 Jan |
|
Angioplasty increases coronary sinus F2-isoprostane formation: evidence for in vivo oxidative stress during PTCA. | 2001 Jan |
|
The PlA polymorphism of glycoprotein IIIa functions as a modifier for the effect of estrogen on platelet aggregation. | 2001 Jan |
|
Endogenous nitric oxide and prostaglandins synergistically counteract thromboembolism in arterioles but not in venules. | 2001 Jan |
|
Disaggregation of in vitro preformed platelet-rich clots by abciximab increases fibrin exposure and promotes fibrinolysis. | 2001 Jan |
|
Low-dose aspirin therapy and periodontal attachment loss in ex- and non-smokers. | 2001 Jan |
|
Selectivity of recombinant human leukotriene D(4), leukotriene B(4), and lipoxin A(4) receptors with aspirin-triggered 15-epi-LXA(4) and regulation of vascular and inflammatory responses. | 2001 Jan |
|
[Leukocytoclastic vasculitis associated with ticlopidine]. | 2001 Jan |
|
Reduced risk of colorectal cancer among long-term users of aspirin and nonaspirin nonsteroidal antiinflammatory drugs. | 2001 Jan |
|
Prevention of pre-eclampsia: status and perspectives 2000. | 2001 Jan |
|
Hemoglobin and methemoglobin concentrations after large-dose infusions of diaspirin cross-linked hemoglobin. | 2001 Jan |
|
Effect of acetylsalicylic acid on endogenous I kappa B kinase activity in lung epithelial cells. | 2001 Jan |
|
Another reason for taking aspirin. | 2001 Jan |
|
Hypothesized treatment for migraines using low doses of tryptophan, niacin, calcium, caffeine, and acetylsalicylic acid. | 2001 Jan |
|
Effect of a high loading dose of clopidogrel on platelet function in patients undergoing coronary stent placement. | 2001 Jan |
|
Increased platelet reactivity and significant changes in coagulation markers after cavopulmonary connection. | 2001 Jan |
|
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis. | 2001 Jan 15 |
|
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism. | 2001 Jan 15 |
|
Blood donations and risk of coronary heart disease in men. | 2001 Jan 2 |
|
Drug Points: tachycardia associated with moxifloxacin. | 2001 Jan 6 |
|
The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa. | 2001 Mar 9 |
Sample Use Guides
Severe pain: Initiate treatment with two capsules (1 capsule contains 16 mg dihydrocodeine bitartrate, 356.4 mg aspirin, and 30 mg caffeine) orally every 4 hours as needed for pain. Headache: One or 2 capsules (1 capsule contains 50 mg butalbital, 325 mg aspirin and 40 mg caffeine) every 4 hours. Total daily dose should not exceed 6 capsules. Prevention of stoke and heart attacks: the recommended dose is one capsule of aspirin (162.5 mg) once daily. Take the capsules with a full glass of water at the same time each day. Prevention of stroke (in combination with dipyridamole): the recommended dose is one capsule (200 mg dipyridamole and 25 mg aspirin) given orally twice daily.
Route of Administration:
Enteral
Human platelet-rich plasma was incubated with various aspirin concentrations (10, 20, 50, 100, 200, 300, 400, 500 uM) at 37C for up to 4.5 h. Platelet aggregation and thromboxane generation were measured. Inhibition of platelet aggregation and thromboxane formation by 10 uM aspirin was maximal by 90 min. There was progressive inhibition by 3 uM aspirin during incubation for 270 min. By the end of this time there was also significant inhibition by 1 uM aspirin.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
33988
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SUB34053
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DTXSID30958944
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD