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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H8O4.C6H14N2O2
Molecular Weight 326.3456
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASPIRIN LYSINE

SMILES

CC(=O)Oc1ccccc1C(=O)O.C(CCN)C[C@@]([H])(C(=O)O)N

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

Molecular Formula C6H14N2O2
Molecular Weight 146.1878
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C9H8O4
Molecular Weight 180.1578
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

-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
Acetyl salicylic acid improves somatosensory evoked potentials in streptozotocin-diabetic rats.
1999 Dec
The use of nimesulide in patients with acetylsalicylic acid and nonsteroidal anti-inflammatory drug intolerance.
1999 Dec
Risk factors for acetaminophen and nimesulide intolerance in patients with NSAID-induced skin disorders.
1999 Jun
Leptin in gastroprotection induced by cholecystokinin or by a meal. Role of vagal and sensory nerves and nitric oxide.
1999 Jun 18
Bleeding during warfarin and aspirin therapy in patients with atrial fibrillation: the AFASAK 2 study. Atrial Fibrillation Aspirin and Anticoagulation.
1999 Jun 28
Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells.
1999 May 21
Capsaicin-sensitive afferent sensory nerves in modulating gastric mucosal defense against noxious agents.
1999 Nov
Prospective study of aspirin use and risk of stroke in women.
1999 Sep
Sulindac inhibits activation of the NF-kappaB pathway.
1999 Sep 17
Dramatic augmentation of a food allergy by acetylsalicylic acid.
2000 Apr
Pharmacotherapies for cocaine dependence.
2000 Dec
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
Intermediate but not low doses of aspirin can suppress angiotensin-converting enzyme inhibitor-induced cough.
2000 Jul
Symptomatic secondary hemorrhagic transformation of ischemic Wallenberg's syndrome.
2000 Jun
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
Aspirin induces apoptosis through mitochondrial cytochrome c release.
2000 Sep 1
Cardiac risk factors, medication, and recurrent clinical events after acute coronary disease; a prospective cohort study.
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
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
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
Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols.
2001 Jan
Endogenous nitric oxide and prostaglandins synergistically counteract thromboembolism in arterioles but not in venules.
2001 Jan
[Leukocytoclastic vasculitis associated with ticlopidine].
2001 Jan
Antithrombotic therapy in cardiac stent patients.
2001 Jan
Anticoagulation and heart failure.
2001 Jan
Is optimal antithrombotic therapy after myocardial infarction well defined?
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
Effect of acetylsalicylic acid on endogenous I kappa B kinase activity in lung epithelial cells.
2001 Jan
Another reason for taking aspirin.
2001 Jan
Increased platelet reactivity and significant changes in coagulation markers after cavopulmonary connection.
2001 Jan
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.
2001 Jan 15
Authors' reply on aspirin for primary prevention.
2001 Jan 20
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:25:00 UTC 2021
Edited
by admin
on Sat Jun 26 10:25:00 UTC 2021
Record UNII
XAN4V337CI
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Jun 26 10:25:01 UTC 2021 , Edited by admin on Sat Jun 26 10:25:01 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
253-723-0
Created by admin on Sat Jun 26 10:25:01 UTC 2021 , Edited by admin on Sat Jun 26 10:25:01 UTC 2021
PRIMARY
PUBCHEM
91626
Created by admin on Sat Jun 26 10:25:01 UTC 2021 , Edited by admin on Sat Jun 26 10:25:01 UTC 2021
PRIMARY
FDA UNII
XAN4V337CI
Created by admin on Sat Jun 26 10:25:01 UTC 2021 , Edited by admin on Sat Jun 26 10:25:01 UTC 2021
PRIMARY
CAS
37933-78-1
Created by admin on Sat Jun 26 10:25:01 UTC 2021 , Edited by admin on Sat Jun 26 10:25:01 UTC 2021
PRIMARY
EVMPD
SUB34053
Created by admin on Sat Jun 26 10:25:01 UTC 2021 , Edited by admin on Sat Jun 26 10:25:01 UTC 2021
PRIMARY
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