ASPIRIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1950)
Entry Type: Small molecule
Molecule Category: Parent
UNII: R16CO5Y76E

Structure
InChI Key BSYNRYMUTXBXSQ-UHFFFAOYSA-N
Smile CC(=O)Oc1ccccc1C(=O)O
InChI
InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H8O4
Molecular Weight 180.16
AlogP 1.31
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 63.6
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 13.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cyclooxygenase inhibitor PubMed PubMed Wikipedia
Primary Target
COX-1
COX-2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 5 Cytochrome P450 family 5A Cytochrome P450 5A1
- - - - 100-100
Enzyme Hydrolase
- - - - 90
Enzyme Oxidoreductase
- 300-100000 - 52000 22-80
Enzyme
- 300-100000 - 52000 22-80
Membrane receptor
- 5000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 96
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Myocardial Infarction 4 D009203 ClinicalTrials
Thrombosis 4 D013927 ClinicalTrials
Coronary Disease 4 D003327 ClinicalTrials
Myocardial Infarction 4 D009203 ClinicalTrials
Cerebral Infarction 3 D002544 ClinicalTrials
Peptic Ulcer 3 D010437 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Esophageal Neoplasms 3 D004938 ClinicalTrials
Diabetes Mellitus 3 D003920 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Cardiomyopathy, Hypertrophic 3 D002312 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Fetal Growth Retardation 3 D005317 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Ischemic Attack, Transient 3 D002546 ClinicalTrials
Brain Infarction 3 D020520 ClinicalTrials
ST Elevation Myocardial Infarction 3 D000072657 ClinicalTrials
Non-ST Elevated Myocardial Infarction 3 D000072658 ClinicalTrials
Meningitis 3 D008581 ClinicalTrials
Ischemic Stroke 3 D000083242 ClinicalTrials
Peptic Ulcer 3 D010437 ClinicalTrials
Polycythemia Vera 3 D011087 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Vascular Diseases 3 D014652 ClinicalTrials
Abortion, Habitual 3 D000026 ClinicalTrials
Colorectal Neoplasms, Hereditary Nonpolyposis 3 D003123 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Retinal Vein Occlusion 3 D012170 ClinicalTrials
Peripheral Arterial Disease 3 D058729 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Angina, Stable 3 D060050 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Infertility 3 D007246 ClinicalTrials
Aortic Valve Stenosis 3 D001024 ClinicalTrials
Thrombocythemia, Essential 3 D013920 ClinicalTrials
Stomach Ulcer 3 D013276 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Colitis, Ulcerative 3 D003093 ClinicalTrials
Cataract 3 D002386 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Bipolar Disorder 3 D001714 ClinicalTrials
Venous Thromboembolism 3 D054556 ClinicalTrials
Intracranial Aneurysm 3 D002532 ClinicalTrials
Osteonecrosis 3 D010020 ClinicalTrials
Psychotic Disorders 3 D011618 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Intracranial Arteriosclerosis 3 D002537 ClinicalTrials
Retinal Artery Occlusion 3 D015356 ClinicalTrials
Rheumatic Heart Disease 3 D012214 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Hemorrhage 3 D006470 ClinicalTrials
Lipid Metabolism Disorders 3 D052439 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Cerebrovascular Disorders 3 D002561 ClinicalTrials
Mucocutaneous Lymph Node Syndrome 3 D009080 ClinicalTrials
Acute Chest Syndrome 3 D056586 ClinicalTrials
Thrombophilia 3 D019851 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Macular Degeneration 3 D008268 ClinicalTrials
Pre-Eclampsia 3 D011225 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Diabetic Retinopathy 3 D003930 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Carcinoma, Squamous Cell 3 D002294 ClinicalTrials
Ischemia 3 D007511 ClinicalTrials
Acute Coronary Syndrome 3 D054058 ClinicalTrials
Adenomatous Polyposis Coli 3 D011125 ClinicalTrials
Varicose Ulcer 3 D014647 ClinicalTrials
Blindness 3 D001766 ClinicalTrials
Gastrointestinal Hemorrhage 3 D006471 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Cardiovascular Diseases 3 D002318 ClinicalTrials
Asthma 3 D001249 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Psychotic Disorders 3 D011618 ClinicalTrials
Pharyngitis 3 D010612 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Duodenal Ulcer 2 D004381 ClinicalTrials
Hypertension, Pulmonary 2 D006976 ClinicalTrials
Acute Lung Injury 2 D055371 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Respiratory Distress Syndrome 2 D012128 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Pneumonia 2 D011014 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Venous Thrombosis 2 D020246 ClinicalTrials
Heart Diseases 2 D006331 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Barrett Esophagus 2 D001471 ClinicalTrials
Pregnancy 2 D011247 ClinicalTrials
Adenoma 2 D000236 ClinicalTrials
Tobacco Use Disorder 2 D014029 ClinicalTrials
Metabolic Syndrome 2 D024821 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Periodontitis 2 D010518 ClinicalTrials
Carotid Stenosis 2 D016893 ClinicalTrials
Lupus Erythematosus, Systemic 2 D008180 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Nasopharyngeal Neoplasms 2 D009303 ClinicalTrials
Placental Insufficiency 2 D010927 ClinicalTrials
Hypercholesterolemia 2 D006937 ClinicalTrials
Sepsis 2 D018805 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 2 D015464 ClinicalTrials
Vitamin D Deficiency 2 D014808 ClinicalTrials
Pneumonia, Viral 2 D011024 ClinicalTrials
Blood Coagulation Disorders 2 D001778 ClinicalTrials
Respiratory Insufficiency 2 D012131 ClinicalTrials
Depressive Disorder, Treatment-Resistant 2 D061218 ClinicalTrials
Disseminated Intravascular Coagulation 2 D004211 ClinicalTrials
Tension-Type Headache 2 D018781 ClinicalTrials
Depressive Disorder, Major 2 D003865 ClinicalTrials
Uterine Cervical Neoplasms 2 D002583 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Herpes Simplex 1 D006561 ClinicalTrials
Ulcer 1 D014456 ClinicalTrials
Neuralgia, Postherpetic 1 D051474 ClinicalTrials
Digestive System Diseases 1 D004066 ClinicalTrials
Inflammation 1 D007249 ClinicalTrials
Leukoplakia, Oral 1 D007972 ClinicalTrials
Head and Neck Neoplasms 1 D006258 ClinicalTrials
Hypertriglyceridemia 1 D015228 ClinicalTrials
Anemia, Sickle Cell 1 D000755 ClinicalTrials
Sleep Initiation and Maintenance Disorders 0 D007319 ClinicalTrials
Adenocarcinoma of Lung 0 D000077192 ClinicalTrials
Fatigue 0 D005221 ClinicalTrials
Fractures, Bone 0 D050723 ClinicalTrials
Adenomyosis 0 D062788 ClinicalTrials
Peripheral Vascular Diseases 0 D016491 ClinicalTrials

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Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
17.03
Injury, poisoning and procedural complications
10.16
Nervous system disorders
9.94
Gastrointestinal disorders
9.85
General disorders and administration site conditions
7.25
Cardiac disorders
5.95
Respiratory, thoracic and mediastinal disorders
5.68
Pregnancy, puerperium and perinatal conditions
4.91
Skin and subcutaneous tissue disorders
4.11
Immune system disorders
3.35
Blood and lymphatic system disorders
3.21
Investigations
2.93
Psychiatric disorders
2.22
Metabolism and nutrition disorders
2.03

Cross References

Resources Reference
CAS NUMBER 50-78-2
ChEBI 15365
ChEMBL CHEMBL25
DrugBank DB00945
DrugCentral 74
EPA CompTox DTXSID5020108
FDA SRS R16CO5Y76E
Human Metabolome Database HMDB0001879
Guide to Pharmacology 4139
KEGG C01405
PDB AIN
PharmGKB PA448497
PubChem 2244
SureChEMBL SCHEMBL1353
ZINC ZINC000000000053
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