Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C9H7O4.Cu |
Molecular Weight | 421.845 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cu++].CC(=O)OC1=CC=CC=C1C([O-])=O.CC(=O)OC2=CC=CC=C2C([O-])=O
InChI
InChIKey=CMDYHTIDHSNRGW-UHFFFAOYSA-L
InChI=1S/2C9H8O4.Cu/c2*1-6(10)13-8-5-3-2-4-7(8)9(11)12;/h2*2-5H,1H3,(H,11,12);/q;;+2/p-2
Molecular Formula | Cu |
Molecular Weight | 63.546 |
Charge | 2 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C9H7O4 |
Molecular Weight | 179.1495 |
Charge | -1 |
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 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 |
---|---|---|---|---|
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 |
---|---|---|
Studies on the modification of renal lesions due to aspirin and oxyphenbutazone in the rat and the effects on the kidney of 2:4 dinitrophenol. | 1976 Jul |
|
Aspirin reduces experimental cerebral blood flow in vivo. | 1999 Jul |
|
Increased risk of intracranial hemorrhage when aspirin is combined with warfarin: A meta-analysis and hypothesis. | 1999 Jul-Aug |
|
Bleeding during warfarin and aspirin therapy in patients with atrial fibrillation: the AFASAK 2 study. Atrial Fibrillation Aspirin and Anticoagulation. | 1999 Jun 28 |
|
Effects of tetrandrine and fangchinoline on experimental thrombosis in mice and human platelet aggregation. | 1999 Mar |
|
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes. | 1999 May |
|
Iron deficiency anaemia and aspirin use in old age. | 1999 Sep |
|
Prospective study of aspirin use and risk of stroke in women. | 1999 Sep |
|
Hypophysectomy and/or peroxisome proliferators strongly influence the levels of phase II xenobiotic metabolizing enzymes in rat testis. | 1999 Sep 30 |
|
Dramatic augmentation of a food allergy by acetylsalicylic acid. | 2000 Apr |
|
Sleep attacks (sleep episodes) with pergolide. | 2000 Apr 15 |
|
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 |
|
Transcriptional regulation of cyclooxygenase-2 gene expression: novel effects of nonsteroidal anti-inflammatory drugs. | 2000 Feb 15 |
|
[Cholestatic hepatitis as a rare side effect of therapy with ticlopidine]. | 2000 Jul |
|
An uncommon case of fluid retention simulating a congestive heart failure after aspirin consumption. | 2000 Jul |
|
Acetaminophen inhibits iNOS gene expression in RAW 264.7 macrophages: differential regulation of NF-kappaB by acetaminophen and salicylates. | 2000 Jun 16 |
|
Effect of vitamin E on aspirin-induced gastric mucosal injury in rats. | 2000 Mar |
|
Randomized comparative trial of triflusal and aspirin following acute myocardial infarction. | 2000 Mar |
|
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 |
|
Renal function and intensive lowering of blood pressure in hypertensive participants of the hypertension optimal treatment (HOT) study. | 2001 Feb |
|
Use of aspirin, epistaxis, and untreated hypertension as risk factors for primary intracerebral hemorrhage in middle-aged and elderly people. | 2001 Feb |
|
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 |
|
Use of antithrombotic agents during pregnancy. | 2001 Jan |
|
Platelet-active drugs : the relationships among dose, effectiveness, and side effects. | 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 |
|
Antithrombotic therapy in cardiac stent patients. | 2001 Jan |
|
Anticoagulation and heart failure. | 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 |
|
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 |
|
Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery. | 2001 Jan 23 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 21:54:15 UTC 2022
by
admin
on
Fri Dec 16 21:54:15 UTC 2022
|
Record UNII |
5DR11472UI
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
31869
Created by
admin on Fri Dec 16 21:54:15 UTC 2022 , Edited by admin on Fri Dec 16 21:54:15 UTC 2022
|
PRIMARY | |||
|
23325-63-5
Created by
admin on Fri Dec 16 21:54:15 UTC 2022 , Edited by admin on Fri Dec 16 21:54:15 UTC 2022
|
PRIMARY | |||
|
245-583-4
Created by
admin on Fri Dec 16 21:54:15 UTC 2022 , Edited by admin on Fri Dec 16 21:54:15 UTC 2022
|
PRIMARY | |||
|
5DR11472UI
Created by
admin on Fri Dec 16 21:54:15 UTC 2022 , Edited by admin on Fri Dec 16 21:54:15 UTC 2022
|
PRIMARY | |||
|
SUB00273MIG
Created by
admin on Fri Dec 16 21:54:15 UTC 2022 , Edited by admin on Fri Dec 16 21:54:15 UTC 2022
|
PRIMARY | |||
|
DTXSID30177875
Created by
admin on Fri Dec 16 21:54:15 UTC 2022 , Edited by admin on Fri Dec 16 21:54:15 UTC 2022
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE | |||
|
PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |