acetylsalicylic acid indications/contra

Stem definitionDrug idCAS RN
74 50-78-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • acetylsalisylic acid
  • aspirin
  • acetylsalicylic acid
  • aspirin sodium
  • aspirin magnesium
  • aspirin potassium
  • aspirin calcium
  • aspirin anhydride
  • aspirin lysine
The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5)
  • Molecular weight: 180.16
  • Formula: C9H8O4
  • CLOGP: 1.02
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 63.60
  • ALOGS: -2.09
  • ROTB: 3

Drug dosage:

DoseUnitRoute
1 tablet O
30 mg O
3 g O
1 g P
3 g R

Approvals:

DateAgencyCompanyOrphan
April 12, 1950 FDA ENDO PHARMS
Jan. 1, 1898 YEAR INTRODUCED

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Gastrointestinal haemorrhage 6609.40 26.21 1898 19288 22476 3342197
Melaena 3048.47 26.21 803 20383 6509 3358164
Anaemia 2706.40 26.21 1208 19978 53125 3311548
Haemoglobin decreased 2105.42 26.21 855 20331 29439 3335234
Upper gastrointestinal haemorrhage 2096.79 26.21 529 20657 3514 3361159
Haematemesis 2005.77 26.21 571 20615 6314 3358359
Gastric haemorrhage 1896.27 26.21 471 20715 2905 3361768
Haemorrhage 1888.61 26.21 705 20481 19216 3345457
Drug hypersensitivity 1768.98 26.21 793 20393 34887 3329786
Gastric ulcer 1686.57 26.21 461 20725 4324 3360349
Cerebral haemorrhage 1614.50 26.21 525 20661 9329 3355344
Rectal haemorrhage 1522.46 26.21 496 20690 8862 3355811
Angioedema 1289.26 26.21 496 20690 14639 3350034
Epistaxis 1214.36 26.21 469 20717 13982 3350691
Hypotension 1142.79 26.21 657 20529 48857 3315816
Duodenal ulcer 1135.14 26.21 294 20892 2184 3362489
International normalised ratio increased 1131.42 26.21 447 20739 14168 3350505
Faeces discoloured 1041.85 26.21 304 20882 3668 3361005
Haematoma 1035.47 26.21 352 20834 7187 3357486
Haemorrhage intracranial 990.46 26.21 313 20873 5026 3359647
Subdural haematoma 979.36 26.21 299 20887 4256 3360417
Completed suicide 940.66 26.21 494 20692 30620 3334053
Toxicity to various agents 893.36 26.21 551 20635 46503 3318170
Gastritis 887.02 26.21 303 20883 6274 3358399
Dizziness 861.15 26.21 648 20538 75864 3288809
Overdose 847.54 26.21 475 20711 33503 3331170
Acute kidney injury 828.50 26.21 536 20650 49147 3315526
Haematuria 824.59 26.21 320 20866 9632 3355041
Intentional overdose 788.67 26.21 350 20836 14875 3349798
Vomiting 748.39 26.21 637 20549 88894 3275779

Pharmacologic Action:

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SourceCodeDescription
ATC A01AD05 ALIMENTARY TRACT AND METABOLISM
STOMATOLOGICAL PREPARATIONS
STOMATOLOGICAL PREPARATIONS
Other agents for local oral treatment
ATC B01AC06 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Platelet aggregation inhibitors excl. heparin
ATC N02BA01 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Salicylic acid and derivatives
ATC B01AC56 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Platelet aggregation inhibitors excl. heparin
ATC C07FX02 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS, OTHER COMBINATIONS
Beta blocking agents, other combinations
ATC C07FX03 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS, OTHER COMBINATIONS
Beta blocking agents, other combinations
ATC C07FX04 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS, OTHER COMBINATIONS
Beta blocking agents, other combinations
ATC C10BX01 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
HMG CoA reductase inhibitors, other combinations
ATC C10BX02 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
HMG CoA reductase inhibitors, other combinations
ATC C10BX04 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
HMG CoA reductase inhibitors, other combinations
ATC C10BX05 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
HMG CoA reductase inhibitors, other combinations
ATC C10BX06 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
HMG CoA reductase inhibitors, other combinations
ATC C10BX08 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
HMG CoA reductase inhibitors, other combinations
ATC C10BX12 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
HMG CoA reductase inhibitors, other combinations
ATC M01BA03 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY/ANTIRHEUMATIC AGENTS IN COMBINATION
Antiinflammatory/antirheumatic agents in combination with corticosteroids
ATC N02AJ02 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with non-opioid analgesics
ATC N02AJ07 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with non-opioid analgesics
ATC N02AJ18 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with non-opioid analgesics
ATC N02BA51 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Salicylic acid and derivatives
ATC N02BA71 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Salicylic acid and derivatives
CHEBI has role CHEBI:73182 plant activator
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:50427 platelet aggregation inhibitor
CHEBI has role CHEBI:35493 antipyretic
CHEBI has role CHEBI:49023 prostaglandin antagonist
CHEBI has role CHEBI:50249 anticoagulant
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35481 non-narcotic analgesic
FDA PE N0000008836 Decreased Prostaglandin Production
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D058633 Antipyretics
MeSH PA D018501 Antirheumatic Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D050299 Fibrin Modulating Agents
MeSH PA D005343 Fibrinolytic Agents
MeSH PA D006401 Hematologic Agents
FDA PE N0000008832 Decreased Platelet Aggregation
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D010975 Platelet Aggregation Inhibitors
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Sinus headache indication 4969004
Pain indication 22253000
Myocardial infarction indication 22298006 DOID:5844
Toothache indication 27355003
Migraine indication 37796009 DOID:6364
Joint pain indication 57676002
Rheumatoid arthritis indication 69896004 DOID:7148
Common cold indication 82272006 DOID:10459
Backache indication 161891005
Headache disorder indication 230461009
Influenza-like symptoms indication 315642008
Osteoarthritis indication 396275006 DOID:381
Arthritic Pain indication

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.57 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
325MG ASPIRIN PLX PHARMA N203697 Jan. 14, 2013 OTC CAPSULE ORAL 9101637 March 23, 2022 TEMPORARY REDUCTION OF FEVER
325MG ASPIRIN PLX PHARMA N203697 Jan. 14, 2013 OTC CAPSULE ORAL 9101637 March 23, 2022 TEMPORARY RELIEF OF MINOR ACHES AND PAINS
325MG ASPIRIN PLX PHARMA N203697 Jan. 14, 2013 OTC CAPSULE ORAL 9101637 March 23, 2022 TREATMENT/PREVENTION OF CARDIOVASCULAR DISEASE
325MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 9364439 May 31, 2022 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
81MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 9364439 May 31, 2022 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
325MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 6926907 Feb. 28, 2023 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
325MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 8206741 Feb. 28, 2023 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
81MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 6926907 Feb. 28, 2023 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
81MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 8206741 Feb. 28, 2023 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
325MG ASPIRIN PLX PHARMA N203697 Jan. 14, 2013 OTC CAPSULE ORAL 9226892 Sept. 29, 2032 TEMPORARY REDUCTION OF FEVER
325MG ASPIRIN PLX PHARMA N203697 Jan. 14, 2013 OTC CAPSULE ORAL 9226892 Sept. 29, 2032 TEMPORARY RELIEF OF MINOR ACHES AND PAINS
325MG ASPIRIN PLX PHARMA N203697 Jan. 14, 2013 OTC CAPSULE ORAL 9226892 Sept. 29, 2032 TREATMENT/PREVENTION OF CARDIOVASCULAR DISEASE
325MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 9539214 March 13, 2033 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
81MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL 9539214 March 13, 2033 TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
325MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL Sept. 14, 2019 NEW COMBINATION
81MG YOSPRALA ARALEZ PHARMS N205103 Sept. 14, 2016 RX TABLET, DELAYED RELEASE ORAL Sept. 14, 2019 NEW COMBINATION

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 5.12 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 5.77 WOMBAT-PK CHEMBL
Gamma-glutamyltranspeptidase 1 Enzyme IC50 4.44 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 5.62 CHEMBL
Acidic phospholipase A2 3 Enzyme Kd 5.20 WOMBAT-PK
Prostaglandin G/H synthase 1 Enzyme IC50 6.52 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 6.46 CHEMBL

External reference:

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IDSource
CHEBI:15365 CHEBI
4017536 VUID
N0000145918 NUI
C0004057 UMLSCUI
D00109 KEGG_DRUG
CHEMBL25 ChEMBL_ID
4995924SMK UNII
132-49-0 SECONDARY_CAS_RN
DB00945 DRUGBANK_ID
4017536 VANDF
34512 MMSL
N0000006582 NDFRT
N0000145918 NDFRT
001587 NDDF
244 MMSL
1191 RXNORM
387458008 SNOMEDCT_US
7947003 SNOMEDCT_US
4223 MMSL
d00170 MMSL
D001241 MESH_DESCRIPTOR_UI
2244 PUBCHEM_CID
AIN PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Fiorinal with Codeine HUMAN PRESCRIPTION DRUG LABEL 4 0023-6010 CAPSULE 325 mg ORAL NDA 20 sections
aspirin and dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 0054-0575 CAPSULE 25 mg ORAL NDA authorized generic 18 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2000 TABLET, FILM COATED 250 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2021 TABLET, COATED 250 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2035 TABLET, COATED 250 mg ORAL NDA 10 sections
EXCEDRIN HUMAN OTC DRUG LABEL 3 0067-2039 TABLET, FILM COATED 250 mg ORAL NDA 9 sections
Excedrin PM Triple Action Caplets HUMAN OTC DRUG LABEL 3 0067-2056 TABLET, COATED 250 mg ORAL OTC monograph not final 9 sections
BUFFERIN HUMAN OTC DRUG LABEL 1 0067-6424 TABLET 81 mg ORAL OTC monograph final 16 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-8103 TABLET, FILM COATED 250 mg ORAL ANDA 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-8104 TABLET, FILM COATED 250 mg ORAL OTC monograph not final 9 sections
Excedrin PM Triple Action Caplets and Excedrin Tension Headache HUMAN OTC DRUG LABEL 5 0067-8147 KIT 250 mg None OTC monograph not final 9 sections
Aspirin and Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 0093-3040 CAPSULE, EXTENDED RELEASE 25 mg ORAL NDA authorized generic 17 sections
good sense aspirin HUMAN OTC DRUG LABEL 1 0113-0259 TABLET, CHEWABLE 81 mg ORAL OTC monograph not final 9 sections
Good Sense aspirin HUMAN OTC DRUG LABEL 1 0113-0274 TABLET, CHEWABLE 81 mg ORAL OTC monograph not final 9 sections
good sense migraine formula HUMAN OTC DRUG LABEL 3 0113-0374 TABLET, FILM COATED 250 mg ORAL ANDA 9 sections
good sense aspirin HUMAN OTC DRUG LABEL 1 0113-0416 TABLET 325 mg ORAL OTC monograph not final 8 sections
good sense aspirin HUMAN OTC DRUG LABEL 1 0113-0467 TABLET, CHEWABLE 81 mg ORAL OTC monograph not final 9 sections
Basic Care Aspirin HUMAN OTC DRUG LABEL 1 0113-0773 TABLET, FILM COATED 325 mg ORAL OTC monograph not final 9 sections
aspirin and dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 0115-1711 CAPSULE, EXTENDED RELEASE 25 mg ORAL ANDA 17 sections
Butalbital, Aspirin and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0143-1785 TABLET 325 mg ORAL ANDA 11 sections
Carisoprodol and Aspirin HUMAN PRESCRIPTION DRUG LABEL 2 0185-0724 TABLET 325 mg ORAL ANDA 12 sections
Carisoprodol, Aspirin and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 3 0185-0749 TABLET 325 mg ORAL ANDA 14 sections
BAYER 500 mg HUMAN OTC DRUG LABEL 1 0280-0029 POWDER 500 mg ORAL Export only 2 sections
Alka-Seltzer Plus Night Cold HUMAN OTC DRUG LABEL 4 0280-0052 TABLET, EFFERVESCENT 500 mg ORAL OTC monograph final 9 sections
Alka-Seltzer Extra Strength HUMAN OTC DRUG LABEL 3 0280-0211 GRANULE, EFFERVESCENT 500 mg ORAL OTC monograph not final 9 sections
Alka-Seltzer Plus HUMAN OTC DRUG LABEL 7 0280-1140 KIT 325 mg None OTC monograph not final 15 sections
Alka-Seltzer Plus HUMAN OTC DRUG LABEL 7 0280-1140 KIT 500 mg None OTC monograph not final 15 sections
Alka-Seltzer Plus Cold Medicine Sparkling Original HUMAN OTC DRUG LABEL 3 0280-1400 TABLET, EFFERVESCENT 325 mg ORAL OTC monograph not final 9 sections
Alka-Seltzer Plus HUMAN OTC DRUG LABEL 3 0280-1410 TABLET, EFFERVESCENT 325 mg ORAL OTC MONOGRAPH FINAL 9 sections
Alka-Seltzer Plus Cold and Cough Formula HUMAN OTC DRUG LABEL 4 0280-1420 TABLET, EFFERVESCENT 325 mg ORAL OTC monograph final 9 sections