Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H8O4.C6H14N2O2 |
Molecular Weight | 326.345 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCCC(N)C(O)=O.CC(=O)OC1=CC=CC=C1C(O)=O
InChI
InChIKey=JJBCTCGUOQYZHK-UHFFFAOYSA-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)
Molecular Formula | C6H14N2O2 |
Molecular Weight | 146.1876 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | C9H8O4 |
Molecular Weight | 180.1574 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
Letter: Aspirin sensitivity: other drugs. | 1975 Feb |
|
Analgesic-induced renal papillary necrosis in the Gunn rat: the comparative nephrotoxicity of aspirin and phenacetin. | 1976 Nov |
|
The use of nimesulide in patients with acetylsalicylic acid and nonsteroidal anti-inflammatory drug intolerance. | 1999 Dec |
|
Statins and peripheral neuropathy. | 1999 Jan |
|
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes. | 1999 May |
|
Prospective study of aspirin use and risk of stroke in women. | 1999 Sep |
|
Dramatic augmentation of a food allergy by acetylsalicylic acid. | 2000 Apr |
|
Randomized comparative trial of triflusal and aspirin following acute myocardial infarction. | 2000 Mar |
|
[Aspirin-induced angioedema of the nape of the neck with naproxen cross-reaction: a case report]. | 2000 May |
|
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 |
|
Use of aspirin, epistaxis, and untreated hypertension as risk factors for primary intracerebral hemorrhage in middle-aged and elderly people. | 2001 Feb |
|
Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation. | 2001 Feb 10 |
|
Heterogenous nature of flow-mediated dilatation in human conduit arteries in vivo: relevance to endothelial dysfunction in hypercholesterolemia. | 2001 Feb 2 |
|
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 |
|
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 |
|
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans. | 2001 Jan |
|
Another reason for taking aspirin. | 2001 Jan |
|
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis. | 2001 Jan 15 |
|
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
|
Drug Points: tachycardia associated with moxifloxacin. | 2001 Jan 6 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:26:37 GMT 2023
by
admin
on
Fri Dec 15 17:26:37 GMT 2023
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Record UNII |
2JJ274J145
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C263
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