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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H8O4.C6H14N2O2
Molecular Weight 326.345
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASPIRIN LYSINE

SMILES

NCCCC[C@H](N)C(O)=O.CC(=O)OC1=C(C=CC=C1)C(O)=O

InChI

InChIKey=JJBCTCGUOQYZHK-ZSCHJXSPSA-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)/t;5-/m.0/s1

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

-3.62620813E11
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

2.00016003E11
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

1.44132486E12
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

9.4322878E11
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
[Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid].
1999 Feb
Seizures induced by NSAID.
1999 Jan
Aspirin and heparin in acute ischaemic stroke in older patients.
1999 Jul
Increased risk of intracranial hemorrhage when aspirin is combined with warfarin: A meta-analysis and hypothesis.
1999 Jul-Aug
Effects of tetrandrine and fangchinoline on experimental thrombosis in mice and human platelet aggregation.
1999 Mar
NSAID-induced bronchospasm--a common and serious problem. A report from MEDSAFE, the New Zealand Medicines and Medical Devices Safety Authority.
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
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria.
2000 Aug
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
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
Aspirin-associated intracerebral hemorrhage: clinical and radiologic features.
2000 Jun 27
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
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
The effects of diaspirin cross-linked hemoglobin on the tone of human saphenous vein.
2001 Feb
Renal function and intensive lowering of blood pressure in hypertensive participants of the hypertension optimal treatment (HOT) study.
2001 Feb
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
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.
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
Use of antithrombotic agents during pregnancy.
2001 Jan
Platelet-active drugs : the relationships among dose, effectiveness, and side effects.
2001 Jan
Gastric mucosal resistance to acute injury in experimental portal hypertension.
2001 Jan
Multiple endothelial injury in epicardial coronary artery induces downstream microvascular spasm as well as remodeling partly via thromboxane A2.
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
Endogenous nitric oxide and prostaglandins synergistically counteract thromboembolism in arterioles but not in venules.
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
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
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
Hypothesized treatment for migraines using low doses of tryptophan, niacin, calcium, caffeine, and acetylsalicylic acid.
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
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
Drug Points: tachycardia associated with moxifloxacin.
2001 Jan 6
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
ASPIRIN LYSINE
Common Name English
LYSINE ACETYLSALICYLATE
Common Name English
FLECTADOL
Brand Name English
LASPAL
Brand Name English
L-LYSINE ACETYLSALICYLATE
Common Name English
ACETYLSALICYLIC ACID LYSINATE
Common Name English
L-LYSINE, 2-(ACETYLOXY)BENZOATE (1:1)
Common Name English
LYSINE ASPIRIN
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 33988
Created by admin on Fri Dec 16 17:25:15 UTC 2022 , Edited by admin on Fri Dec 16 17:25:15 UTC 2022
Code System Code Type Description
ECHA (EC/EINECS)
253-723-0
Created by admin on Fri Dec 16 17:25:15 UTC 2022 , Edited by admin on Fri Dec 16 17:25:15 UTC 2022
PRIMARY
PUBCHEM
91626
Created by admin on Fri Dec 16 17:25:15 UTC 2022 , Edited by admin on Fri Dec 16 17:25:15 UTC 2022
PRIMARY
FDA UNII
XAN4V337CI
Created by admin on Fri Dec 16 17:25:15 UTC 2022 , Edited by admin on Fri Dec 16 17:25:15 UTC 2022
PRIMARY
CAS
37933-78-1
Created by admin on Fri Dec 16 17:25:15 UTC 2022 , Edited by admin on Fri Dec 16 17:25:15 UTC 2022
PRIMARY
EVMPD
SUB34053
Created by admin on Fri Dec 16 17:25:15 UTC 2022 , Edited by admin on Fri Dec 16 17:25:15 UTC 2022
PRIMARY
EPA CompTox
DTXSID30958944
Created by admin on Fri Dec 16 17:25:15 UTC 2022 , Edited by admin on Fri Dec 16 17:25:15 UTC 2022
PRIMARY