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

Details

Stereochemistry ACHIRAL
Molecular Formula C9H7O4.Na
Molecular Weight 202.1396
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASPIRIN SODIUM

SMILES

CC(=O)Oc1ccccc1C(=O)[O-].[Na+]

InChI

InChIKey=JZLOKWGVGHYBKD-UHFFFAOYSA-M
InChI=1S/C9H8O4.Na/c1-6(10)13-8-5-3-2-4-7(8)9(11)12;/h2-5H,1H3,(H,11,12);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula C9H7O4
Molecular Weight 179.1498
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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
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
Analgesic-induced renal papillary necrosis in the Gunn rat: the comparative nephrotoxicity of aspirin and phenacetin.
1976 Nov
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
Seizures induced by NSAID.
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
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
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
Regular use of analgesics is a risk factor for renal cell carcinoma.
1999 Oct
Iron deficiency anaemia and aspirin use in old age.
1999 Sep
Spontaneous compartment syndrome after thrombolytic therapy.
1999 Sep
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
Sulindac inhibits activation of the NF-kappaB pathway.
1999 Sep 17
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
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
Symptomatic secondary hemorrhagic transformation of ischemic Wallenberg's syndrome.
2000 Jun
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
Clinical, biochemical, and genetic characterization of a novel estrogen-dependent inherited form of angioedema.
2000 Sep
Human herpesvirus 8 K1-associated nuclear factor-kappa B-dependent promoter activity: role in Kaposi's sarcoma inflammation?
2001
Cardiac risk factors, medication, and recurrent clinical events after acute coronary disease; a prospective cohort 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
Heterogenous nature of flow-mediated dilatation in human conduit arteries in vivo: relevance to endothelial dysfunction in hypercholesterolemia.
2001 Feb 2
Antithrombotic agents in coronary artery disease.
2001 Jan
Antithrombotic therapy in atrial fibrillation.
2001 Jan
Multiple endothelial injury in epicardial coronary artery induces downstream microvascular spasm as well as remodeling partly via thromboxane A2.
2001 Jan
Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols.
2001 Jan
Anticoagulation and heart failure.
2001 Jan
Is optimal antithrombotic therapy after myocardial infarction well defined?
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
Effect of acetylsalicylic acid on endogenous I kappa B kinase activity in lung epithelial cells.
2001 Jan
Hypothesized treatment for migraines using low doses of tryptophan, niacin, calcium, caffeine, and acetylsalicylic acid.
2001 Jan
Effect of a high loading dose of clopidogrel on platelet function in patients undergoing coronary stent placement.
2001 Jan
Low-grade exercise enhances platelet aggregability in patients with obstructive coronary disease independently of myocardial ischemia.
2001 Jan 1
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.
2001 Jan 15
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism.
2001 Jan 15
Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery.
2001 Jan 23
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 Sat Jun 26 09:57:20 UTC 2021
Edited
by admin
on Sat Jun 26 09:57:20 UTC 2021
Record UNII
E62HT5S2E9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASPIRIN SODIUM
Common Name English
BENZOIC ACID, 2-(ACETYLOXY)-, SODIUM SALT (1:1)
Common Name English
SALICYLIC ACID ACETATE, SODIUM SALT
Common Name English
BENZOIC ACID, 2-(ACETYLOXY)-, SODIUM SALT
Common Name English
ACETYLSALICYLATE SODIUM
VANDF   WHO-DD  
Systematic Name English
SALICYLIC ACID, ACETATE, SODIUM SALT
Common Name English
ACETYLSALICYLATE SODIUM [VANDF]
Common Name English
SODIUM O-ACETYLOXYBENZOATE
Common Name English
SODIUM ACETYLSALICYLATE
Systematic Name English
SODIUM O-ACETOXYBENZOATE
Common Name English
ACETYLSALICYLATE SODIUM [WHO-DD]
Common Name English
ACETYLSALICYLIC ACID, SODIUM SALT
Common Name English
SODIUM ACETYLSALICYLIC ACID
Systematic Name English
SODIUM ASPIRIN
Common Name English
ASPIRIN SODIUM SALT
Common Name English
Code System Code Type Description
CAS
493-53-8
Created by admin on Sat Jun 26 09:57:20 UTC 2021 , Edited by admin on Sat Jun 26 09:57:20 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-777-7
Created by admin on Sat Jun 26 09:57:20 UTC 2021 , Edited by admin on Sat Jun 26 09:57:20 UTC 2021
PRIMARY
PUBCHEM
23666729
Created by admin on Sat Jun 26 09:57:20 UTC 2021 , Edited by admin on Sat Jun 26 09:57:20 UTC 2021
PRIMARY
FDA UNII
E62HT5S2E9
Created by admin on Sat Jun 26 09:57:20 UTC 2021 , Edited by admin on Sat Jun 26 09:57:20 UTC 2021
PRIMARY
RXCUI
314293
Created by admin on Sat Jun 26 09:57:20 UTC 2021 , Edited by admin on Sat Jun 26 09:57:20 UTC 2021
PRIMARY RxNorm
EVMPD
SUB12729MIG
Created by admin on Sat Jun 26 09:57:20 UTC 2021 , Edited by admin on Sat Jun 26 09:57:20 UTC 2021
PRIMARY
EPA CompTox
493-53-8
Created by admin on Sat Jun 26 09:57:20 UTC 2021 , Edited by admin on Sat Jun 26 09:57:20 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE