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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
Letter: Aspirin sensitivity: other drugs.
1975 Feb
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
Statins and peripheral neuropathy.
1999 Jan
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes.
1999 May
Prospective study of aspirin use and risk of stroke in women.
1999 Sep
Dramatic augmentation of a food allergy by acetylsalicylic acid.
2000 Apr
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
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
Gastric mucosal resistance to acute injury in experimental portal hypertension.
2001 Jan
Angioplasty increases coronary sinus F2-isoprostane formation: evidence for in vivo oxidative stress during PTCA.
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
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans.
2001 Jan
Another reason for taking aspirin.
2001 Jan
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.
2001 Jan 15
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.
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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