U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of Aspirin Trelamine

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

HIDE SMILES / InChI

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.

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
Antiplatelet drugs for prevention of pre-eclampsia and its consequences: systematic review.
2001-02-10
Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation.
2001-02-10
Heterogenous nature of flow-mediated dilatation in human conduit arteries in vivo: relevance to endothelial dysfunction in hypercholesterolemia.
2001-02-02
Cardiac risk factors, medication, and recurrent clinical events after acute coronary disease; a prospective cohort study.
2001-02
Non-steroidal anti-inflammatory drugs and gastrointestinal damage-problems and solutions.
2001-02
A novel synthetic inhibitor of factor Xa decreases early reocclusion and improves 24-h patency after coronary fibrinolysis in dogs.
2001-02
The effects of diaspirin cross-linked hemoglobin on the tone of human saphenous vein.
2001-02
Renal function and intensive lowering of blood pressure in hypertensive participants of the hypertension optimal treatment (HOT) study.
2001-02
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).
2001-02
Use of aspirin, epistaxis, and untreated hypertension as risk factors for primary intracerebral hemorrhage in middle-aged and elderly people.
2001-02
Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery.
2001-01-23
Authors' reply on aspirin for primary prevention.
2001-01-20
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.
2001-01-15
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism.
2001-01-15
Drug Points: tachycardia associated with moxifloxacin.
2001-01-06
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.
2001-01-05
Blood donations and risk of coronary heart disease in men.
2001-01-02
Local delivery of enoxaparin to decrease restenosis after stenting: results of initial multicenter trial: Polish-American Local Lovenox NIR Assessment study (The POLONIA study).
2001-01-02
Low-grade exercise enhances platelet aggregability in patients with obstructive coronary disease independently of myocardial ischemia.
2001-01-01
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.
2001-01
Present treatment options for unstable angina and non-Q-wave myocardial infarction.
2001-01
Antithrombotic agents in coronary artery disease.
2001-01
Antithrombotic therapy in patients with mechanical and biological prosthetic heart valves.
2001-01
Antithrombotic therapy in atrial fibrillation.
2001-01
Use of antithrombotic agents during pregnancy.
2001-01
Platelet-active drugs : the relationships among dose, effectiveness, and side effects.
2001-01
Gastric mucosal resistance to acute injury in experimental portal hypertension.
2001-01
Angioplasty increases coronary sinus F2-isoprostane formation: evidence for in vivo oxidative stress during PTCA.
2001-01
Multiple endothelial injury in epicardial coronary artery induces downstream microvascular spasm as well as remodeling partly via thromboxane A2.
2001-01
Lp(a) lipoprotein--an independent risk factor for coronary heart disease after menopause.
2001-01
The PlA polymorphism of glycoprotein IIIa functions as a modifier for the effect of estrogen on platelet aggregation.
2001-01
Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols.
2001-01
Endogenous nitric oxide and prostaglandins synergistically counteract thromboembolism in arterioles but not in venules.
2001-01
Disaggregation of in vitro preformed platelet-rich clots by abciximab increases fibrin exposure and promotes fibrinolysis.
2001-01
Low-dose aspirin therapy and periodontal attachment loss in ex- and non-smokers.
2001-01
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.
2001-01
[Leukocytoclastic vasculitis associated with ticlopidine].
2001-01
Antithrombotic therapy in cardiac stent patients.
2001-01
Anticoagulation and heart failure.
2001-01
Is optimal antithrombotic therapy after myocardial infarction well defined?
2001-01
Reduced risk of colorectal cancer among long-term users of aspirin and nonaspirin nonsteroidal antiinflammatory drugs.
2001-01
Diabetes mellitus with left transverse sinus thrombosis and right transverse sinus aplasia.
2001-01
Active-control trials: how would a new agent compare with placebo? A method illustrated with clopidogrel, aspirin, and placebo.
2001-01
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans.
2001-01
Prevention of pre-eclampsia: status and perspectives 2000.
2001-01
Hemoglobin and methemoglobin concentrations after large-dose infusions of diaspirin cross-linked hemoglobin.
2001-01
Effect of acetylsalicylic acid on endogenous I kappa B kinase activity in lung epithelial cells.
2001-01
Novel platelet inhibitors.
2001
Human herpesvirus 8 K1-associated nuclear factor-kappa B-dependent promoter activity: role in Kaposi's sarcoma inflammation?
2001
Letter: Aspirin sensitivity: other drugs.
1975-02
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:36:50 GMT 2025
Edited
by admin
on Mon Mar 31 18:36:50 GMT 2025
Record UNII
JKW59XM343
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EDAN
WHO-DD  
Preferred Name English
Aspirin Trelamine
USAN  
Official Name English
2-(Diethylamino)ethyl 2-acetoxybenzoate
Systematic Name English
X-0023
Code English
2-(ACETYLOXY)BENZOIC ACID 2-(DIETHYLAMINO)ETHYL ESTER
Systematic Name English
ASPIRIN TRELAMINE [USAN]
Common Name English
Benzoic acid, 2-(acetyloxy)-, 2-(diethylamino)ethyl ester
Systematic Name English
Edan [WHO-DD]
Common Name English
TF-0023
Code English
SALICYLIC ACID, 2-(DIETHYLAMINO)ETHYL ESTER, ACETATE
Systematic Name English
Code System Code Type Description
SMS_ID
300000040210
Created by admin on Mon Mar 31 18:36:50 GMT 2025 , Edited by admin on Mon Mar 31 18:36:50 GMT 2025
PRIMARY
FDA UNII
JKW59XM343
Created by admin on Mon Mar 31 18:36:50 GMT 2025 , Edited by admin on Mon Mar 31 18:36:50 GMT 2025
PRIMARY
NCI_THESAURUS
C203171
Created by admin on Mon Mar 31 18:36:50 GMT 2025 , Edited by admin on Mon Mar 31 18:36:50 GMT 2025
PRIMARY
PUBCHEM
10245201
Created by admin on Mon Mar 31 18:36:50 GMT 2025 , Edited by admin on Mon Mar 31 18:36:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID80222228
Created by admin on Mon Mar 31 18:36:50 GMT 2025 , Edited by admin on Mon Mar 31 18:36:50 GMT 2025
PRIMARY
CAS
7194-12-9
Created by admin on Mon Mar 31 18:36:50 GMT 2025 , Edited by admin on Mon Mar 31 18:36:50 GMT 2025
PRIMARY
USAN
LM-73
Created by admin on Mon Mar 31 18:36:50 GMT 2025 , Edited by admin on Mon Mar 31 18:36:50 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY