Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H21NO4 |
| Molecular Weight | 279.3315 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCOC(=O)C1=CC=CC=C1OC(C)=O
InChI
InChIKey=GHIVDTCFLFLOBV-UHFFFAOYSA-N
InChI=1S/C15H21NO4/c1-4-16(5-2)10-11-19-15(18)13-8-6-7-9-14(13)20-12(3)17/h6-9H,4-5,10-11H2,1-3H3
| Molecular Formula | C15H21NO4 |
| Molecular Weight | 279.3315 |
| 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.
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 Date-3.62620813E11 |
|||
| 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 Date2.00016003E11 |
|||
| 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 Date1.44132486E12 |
|||
| 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 Date9.4322878E11 |
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 |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
Page: - |
yes | |||
| yes | ||||
| yes | ||||
| yes | ||||
Page: - |
yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [Km 1242 uM] | ||||
| yes [Km 2337 uM] | ||||
| yes [Km 278.6 uM] | ||||
| yes [Km 40.7 uM] | ||||
| yes [Km 683.1 uM] | ||||
| yes [Km 698.2 uM] | ||||
| yes [Km 94.2 uM] | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Analgesic-induced renal papillary necrosis in the Gunn rat: the comparative nephrotoxicity of aspirin and phenacetin. | 1976 Nov |
|
| Risk factors for acetaminophen and nimesulide intolerance in patients with NSAID-induced skin disorders. | 1999 Jun |
|
| Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes. | 1999 May |
|
| Hypophysectomy and/or peroxisome proliferators strongly influence the levels of phase II xenobiotic metabolizing enzymes in rat testis. | 1999 Sep 30 |
|
| Transcriptional regulation of cyclooxygenase-2 gene expression: novel effects of nonsteroidal anti-inflammatory drugs. | 2000 Feb 15 |
|
| Effect of vitamin E on aspirin-induced gastric mucosal injury in rats. | 2000 Mar |
|
| 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 |
|
| 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 |
|
| Antithrombotic agents in coronary artery disease. | 2001 Jan |
|
| Antithrombotic therapy in patients with mechanical and biological prosthetic heart valves. | 2001 Jan |
|
| Antithrombotic therapy in atrial fibrillation. | 2001 Jan |
|
| Use of antithrombotic agents during pregnancy. | 2001 Jan |
|
| Lp(a) lipoprotein--an independent risk factor for coronary heart disease after menopause. | 2001 Jan |
|
| The PlA polymorphism of glycoprotein IIIa functions as a modifier for the effect of estrogen on platelet aggregation. | 2001 Jan |
|
| Anticoagulation and heart failure. | 2001 Jan |
|
| Reduced risk of colorectal cancer among long-term users of aspirin and nonaspirin nonsteroidal antiinflammatory drugs. | 2001 Jan |
|
| Diabetes mellitus with left transverse sinus thrombosis and right transverse sinus aplasia. | 2001 Jan |
|
| Low-grade exercise enhances platelet aggregability in patients with obstructive coronary disease independently of myocardial ischemia. | 2001 Jan 1 |
|
| 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 |
|
| Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 21:05:32 UTC 2022
by
admin
on
Fri Dec 16 21:05:32 UTC 2022
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| Record UNII |
JKW59XM343
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| Record Status |
Validated (UNII)
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| Record Version |
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10245201
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DTXSID80222228
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7194-12-9
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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