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

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

Molecular Formula C9H8O4
Molecular Weight 180.1574
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
[Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid].
1999 Feb
Statins and peripheral neuropathy.
1999 Jan
Aspirin and heparin in acute ischaemic stroke in older patients.
1999 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
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
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
Sleep attacks (sleep episodes) with pergolide.
2000 Apr 15
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
Intermediate but not low doses of aspirin can suppress angiotensin-converting enzyme inhibitor-induced cough.
2000 Jul
Aspirin-associated intracerebral hemorrhage: clinical and radiologic features.
2000 Jun 27
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-induced angioedema of the nape of the neck with naproxen cross-reaction: a case report].
2000 May
The role of hydroxyl radical as a messenger in Cr(VI)-induced p53 activation.
2000 Sep
Cardiac risk factors, medication, and recurrent clinical events after acute coronary disease; a prospective cohort study.
2001 Feb
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
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
Diabetes mellitus with left transverse sinus thrombosis and right transverse sinus aplasia.
2001 Jan
Increased platelet reactivity and significant changes in coagulation markers after cavopulmonary connection.
2001 Jan
Blood donations and risk of coronary heart disease in men.
2001 Jan 2
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:02:46 UTC 2023
Edited
by admin
on Wed Jul 05 23:02:46 UTC 2023
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 Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
253-723-0
Created by admin on Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
PRIMARY
PUBCHEM
91626
Created by admin on Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
PRIMARY
FDA UNII
XAN4V337CI
Created by admin on Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
PRIMARY
CAS
37933-78-1
Created by admin on Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
PRIMARY
EVMPD
SUB34053
Created by admin on Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
PRIMARY
SMS_ID
100000127914
Created by admin on Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID30958944
Created by admin on Wed Jul 05 23:02:46 UTC 2023 , Edited by admin on Wed Jul 05 23:02:46 UTC 2023
PRIMARY
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