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

Details

Stereochemistry RACEMIC
Molecular Formula C9H8O4.C6H14N2O2
Molecular Weight 326.345
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASPIRIN DL-LYSINE

SMILES

NCCCCC(N)C(O)=O.CC(=O)OC1=CC=CC=C1C(O)=O

InChI

InChIKey=JJBCTCGUOQYZHK-UHFFFAOYSA-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)

HIDE SMILES / InChI

Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

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
Studies on the modification of renal lesions due to aspirin and oxyphenbutazone in the rat and the effects on the kidney of 2:4 dinitrophenol.
1976 Jul
Severe gastrointestinal hemorrhage and anemia after therapeutic doses of aspirin in normal children.
1976 Mar
Analgesic-induced renal papillary necrosis in the Gunn rat: the comparative nephrotoxicity of aspirin and phenacetin.
1976 Nov
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
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
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
Effects of tetrandrine and fangchinoline on experimental thrombosis in mice and human platelet aggregation.
1999 Mar
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes.
1999 May
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
Spontaneous compartment syndrome after thrombolytic therapy.
1999 Sep
Hypophysectomy and/or peroxisome proliferators strongly influence the levels of phase II xenobiotic metabolizing enzymes in rat testis.
1999 Sep 30
Sleep attacks (sleep episodes) with pergolide.
2000 Apr 15
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria.
2000 Aug
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
Intermediate but not low doses of aspirin can suppress angiotensin-converting enzyme inhibitor-induced cough.
2000 Jul
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
Aspirin-associated intracerebral hemorrhage: clinical and radiologic features.
2000 Jun 27
[Aspirin-induced angioedema of the nape of the neck with naproxen cross-reaction: a case report].
2000 May
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
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.
2001 Jan
Platelet-active drugs : the relationships among dose, effectiveness, and side effects.
2001 Jan
Angioplasty increases coronary sinus F2-isoprostane formation: evidence for in vivo oxidative stress during PTCA.
2001 Jan
Multiple endothelial injury in epicardial coronary artery induces downstream microvascular spasm as well as remodeling partly via thromboxane A2.
2001 Jan
Disaggregation of in vitro preformed platelet-rich clots by abciximab increases fibrin exposure and promotes fibrinolysis.
2001 Jan
Low-dose aspirin therapy and periodontal attachment loss in ex- and non-smokers.
2001 Jan
Is optimal antithrombotic therapy after myocardial infarction well defined?
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
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism.
2001 Jan 15
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 Jan 2
Authors' reply on aspirin for primary prevention.
2001 Jan 20
Drug Points: tachycardia associated with moxifloxacin.
2001 Jan 6
The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa.
2001 Mar 9
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 Fri Dec 15 17:26:37 GMT 2023
Edited
by admin
on Fri Dec 15 17:26:37 GMT 2023
Record UNII
2JJ274J145
Record Status Validated (UNII)
Record Version
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Name Type Language
ASPIRIN DL-LYSINE
JAN  
Common Name English
ACETYLSALICYLATE LYSINE
WHO-DD  
Systematic Name English
DL-LYSINE-ACETYLSALICYLATE
Common Name English
ASPIRIN DL-LYSINE [JAN]
Common Name English
Acetylsalicylate lysine [WHO-DD]
Common Name English
LYSINE ASPIRIN [MART.]
Common Name English
SOLPIRIN
Brand Name English
EGICALM
Common Name English
DL-LYSINE ACETYLSALICYLATE
Common Name English
ASPEGIC
Common Name English
DL-LYSINE ACETYLSALICYLATE [EP MONOGRAPH]
Common Name English
VENOPIRIN
Brand Name English
ASPIRISINE
Common Name English
ASPIDOL
Common Name English
VETALGINE
Brand Name English
LYSINE ACETYLSALICYLATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C263
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
Code System Code Type Description
EVMPD
SUB12727MIG
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
PUBCHEM
44219
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
EVMPD
SUB34053
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
MERCK INDEX
m6968
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C91032
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
FDA UNII
2JJ274J145
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID50886518
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
CAS
62952-06-1
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
SMS_ID
100000091435
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
263-769-3
Created by admin on Fri Dec 15 17:26:37 GMT 2023 , Edited by admin on Fri Dec 15 17:26:37 GMT 2023
PRIMARY
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