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Details

Stereochemistry ACHIRAL
Molecular Formula C11H12O4
Molecular Weight 208.2106
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYL ACETYLSALICYLATE

SMILES

CCOC(=O)C1=C(OC(C)=O)C=CC=C1

InChI

InChIKey=UYDSGXAKLVZWIJ-UHFFFAOYSA-N
InChI=1S/C11H12O4/c1-3-14-11(13)9-6-4-5-7-10(9)15-8(2)12/h4-7H,3H2,1-2H3

HIDE SMILES / InChI
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

Curator's Comment: The penetration of the blood-brain barrier was studied in animals.

Originator

Curator's Comment: Felix Hoffmann discovered aspirin when working for Friedrich Bayer & Co. # Bayer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SYNALGOS-DC

Approved Use

SYNALGOS-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

1958
Primary
FIORINAL

Approved Use

FIORINAL 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 Date

1976
Preventing
DURLAZA

Approved Use

DURLAZA 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 Date

2015
Preventing
AGGRENOX

Approved Use

AGGRENOX 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 Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
54.25 mg/L
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
10.31 mg × h/L
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.322 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
68%
ASPIRIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical 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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Letter: Aspirin sensitivity: other drugs.
1975 Feb
Severe gastrointestinal hemorrhage and anemia after therapeutic doses of aspirin in normal children.
1976 Mar
Acetyl salicylic acid improves somatosensory evoked potentials in streptozotocin-diabetic rats.
1999 Dec
Capsaicin-sensitive afferent sensory nerves in modulating gastric mucosal defense against noxious agents.
1999 Nov
Iron deficiency anaemia and aspirin use in old age.
1999 Sep
Spontaneous compartment syndrome after thrombolytic therapy.
1999 Sep
Dramatic augmentation of a food allergy by acetylsalicylic acid.
2000 Apr
Pharmacotherapies for cocaine dependence.
2000 Dec
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
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
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
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
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
Antiplatelet drugs for prevention of pre-eclampsia and its consequences: systematic review.
2001 Feb 10
Heterogenous nature of flow-mediated dilatation in human conduit arteries in vivo: relevance to endothelial dysfunction in hypercholesterolemia.
2001 Feb 2
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
Antithrombotic therapy in patients with mechanical and biological prosthetic heart valves.
2001 Jan
Antithrombotic therapy in atrial fibrillation.
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
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
Anticoagulation and heart failure.
2001 Jan
Is optimal antithrombotic therapy after myocardial infarction well defined?
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
Active-control trials: how would a new agent compare with placebo? A method illustrated with clopidogrel, aspirin, and placebo.
2001 Jan
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans.
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
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
Blood donations and risk of coronary heart disease in men.
2001 Jan 2
Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery.
2001 Jan 23
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.
2001 Jan 5
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Name Type Language
ETHYL ACETYLSALICYLATE
Systematic Name English
2-ACETOXYBENZOIC ACID ETHYL ESTER
Systematic Name English
ETHYL 2-ACETYLOXYBENZOATE
Systematic Name English
Code System Code Type Description
FDA UNII
VX19C5613T
Created by admin on Fri Dec 15 15:46:16 GMT 2023 , Edited by admin on Fri Dec 15 15:46:16 GMT 2023
PRIMARY
PUBCHEM
10728
Created by admin on Fri Dec 15 15:46:16 GMT 2023 , Edited by admin on Fri Dec 15 15:46:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID60200948
Created by admin on Fri Dec 15 15:46:16 GMT 2023 , Edited by admin on Fri Dec 15 15:46:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-467-4
Created by admin on Fri Dec 15 15:46:16 GMT 2023 , Edited by admin on Fri Dec 15 15:46:16 GMT 2023
PRIMARY
CAS
529-68-0
Created by admin on Fri Dec 15 15:46:16 GMT 2023 , Edited by admin on Fri Dec 15 15:46:16 GMT 2023
PRIMARY