CHEBI:15365 - acetylsalicylic acid

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ChEBI Name acetylsalicylic acid
ChEBI ID CHEBI:15365
Definition A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:2890, CHEBI:40705, CHEBI:71414, CHEBI:22188, CHEBI:22203
Supplier Information ChemicalBook:CB5114818, ChemicalBook:CB4421683, eMolecules:474821, Selleckchem:aspirin-acetylsalicylic-acid, ZINC000000000053
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Aspirin is the genericized trademark for acetylsalicylic acid (ASA), a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and inflammation, and as an antithrombotic. Specific inflammatory conditions that aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin is also used long-term to help prevent further heart attacks, ischaemic strokes, and blood clots in people at high risk. For pain or fever, effects typically begin within 30 minutes. Aspirin works similarly to other NSAIDs but also suppresses the normal functioning of platelets. One common adverse effect is an upset stomach. More significant side effects include stomach ulcers, stomach bleeding, and worsening asthma. Bleeding risk is greater among those who are older, drink alcohol, take other NSAIDs, or are on other blood thinners. Aspirin is not recommended in the last part of pregnancy. It is not generally recommended in children with infections because of the risk of Reye syndrome. High doses may result in ringing in the ears. A precursor to aspirin found in the bark of the willow tree (genus Salix) has been used for its health effects for at least 2,400 years. In 1853, chemist Charles Frédéric Gerhardt treated the medicine sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first time. Over the next 50 years, other chemists, mostly of the German company Bayer, established the chemical structure and devised more efficient production methods.: 69–75  Felix Hoffmann (or Arthur Eichengrün) of Bayer was the first to produce acetylsalicylic acid in a pure, stable form in 1897. By 1899, Bayer had dubbed this drug Aspirin and was selling it globally.: 27  Aspirin is available without medical prescription as a proprietary or generic medication in most jurisdictions. It is one of the most widely used medications globally, with an estimated 40,000 tonnes (44,000 tons) (50 to 120 billion pills) consumed each year, and is on the World Health Organization's List of Essential Medicines. In 2022, it was the 36th most commonly prescribed medication in the United States, with more than 16 million prescriptions.
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Formula C9H8O4
Net Charge 0
Average Mass 180.15740
Monoisotopic Mass 180.04226
InChI InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChIKey BSYNRYMUTXBXSQ-UHFFFAOYSA-N
SMILES CC(=O)Oc1ccccc1C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): drug allergen
Any drug which causes the onset of an allergic reaction.
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of prostaglandin-F synthase (EC 1.1.1.188).
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
prostaglandin antagonist
A compound that inhibits the action of prostaglandins.
teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Application(s): plant activator
Any compound that protects plants by activating their defence mechanisms.
drug allergen
Any drug which causes the onset of an allergic reaction.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
prostaglandin antagonist
A compound that inhibits the action of prostaglandins.
anticoagulant
An agent that prevents blood clotting.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing acetylsalicylic acid (CHEBI:15365) has functional parent salicylic acid (CHEBI:16914)
acetylsalicylic acid (CHEBI:15365) has role anticoagulant (CHEBI:50249)
acetylsalicylic acid (CHEBI:15365) has role antipyretic (CHEBI:35493)
acetylsalicylic acid (CHEBI:15365) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
acetylsalicylic acid (CHEBI:15365) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
acetylsalicylic acid (CHEBI:15365) has role drug allergen (CHEBI:88188)
acetylsalicylic acid (CHEBI:15365) has role EC 1.1.1.188 (prostaglandin-F synthase) inhibitor (CHEBI:77425)
acetylsalicylic acid (CHEBI:15365) has role geroprotector (CHEBI:176497)
acetylsalicylic acid (CHEBI:15365) has role non-narcotic analgesic (CHEBI:35481)
acetylsalicylic acid (CHEBI:15365) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
acetylsalicylic acid (CHEBI:15365) has role plant activator (CHEBI:73182)
acetylsalicylic acid (CHEBI:15365) has role platelet aggregation inhibitor (CHEBI:50427)
acetylsalicylic acid (CHEBI:15365) has role prostaglandin antagonist (CHEBI:49023)
acetylsalicylic acid (CHEBI:15365) has role teratogenic agent (CHEBI:50905)
acetylsalicylic acid (CHEBI:15365) is a benzoic acids (CHEBI:22723)
acetylsalicylic acid (CHEBI:15365) is a phenyl acetates (CHEBI:140310)
acetylsalicylic acid (CHEBI:15365) is a salicylates (CHEBI:26596)
acetylsalicylic acid (CHEBI:15365) is conjugate acid of acetylsalicylate (CHEBI:13719)
Incoming 2-acetyloxy-4-pentadecylbenzoic acid (CHEBI:149780) has functional parent acetylsalicylic acid (CHEBI:15365)
aspirin-based probe AP (CHEBI:141699) has functional parent acetylsalicylic acid (CHEBI:15365)
Yosprala (CHEBI:134674) has part acetylsalicylic acid (CHEBI:15365)
acetylsalicylate (CHEBI:13719) is conjugate base of acetylsalicylic acid (CHEBI:15365)
IUPAC Name
2-(acetyloxy)benzoic acid
INNs Sources
acide acétylsalicylique ChemIDplus
ácido acetilsalicílico NIST Chemistry WebBook
acidum acetylsalicylicum NIST Chemistry WebBook
Synonyms Sources
2-(ACETYLOXY)BENZOIC ACID PDBeChem
2-Acetoxybenzenecarboxylic acid KEGG COMPOUND
2-acetoxybenzoic acid ChemIDplus
Acetylsalicylate KEGG COMPOUND
Acetylsalicylic acid KEGG COMPOUND
Acetylsalicylsäure ChemIDplus
acide 2-(acétyloxy)benzoïque IUPAC
ASA ChemIDplus
Aspirin KEGG COMPOUND
Azetylsalizylsäure ChEBI
o-acetoxybenzoic acid NIST Chemistry WebBook
O-acetylsalicylic acid ChemIDplus
o-carboxyphenyl acetate NIST Chemistry WebBook
salicylic acid acetate ChemIDplus
Brand Name Source
Easprin KEGG DRUG
Manual Xrefs Databases
74 DrugCentral
AIN PDBeChem
Aspirin Wikipedia
C01405 KEGG COMPOUND
CPD-524 MetaCyc
D00109 KEGG DRUG
DB00945 DrugBank
HMDB0001879 HMDB
LSM-5288 LINCS
View more database links
Registry Numbers Types Sources
218864 Gmelin Registry Number Gmelin
50-78-2 CAS Registry Number NIST Chemistry WebBook
50-78-2 CAS Registry Number ChemIDplus
779271 Reaxys Registry Number Reaxys
Citations
Ayyadevara S, Bharill P, Dandapat A, Hu C, Khaidakov M, Mitra S, Shmookler Reis RJ, Mehta JL (2013)
Aspirin inhibits oxidant stress, reduces age-associated functional declines, and extends lifespan of Caenorhabditis elegans.
Antioxidants & redox signaling 18, 481-490 [PubMed:22866967]
[show Abstract]
Lanas A, Wu P, Medin J, Mills EJ (2011)
Low doses of acetylsalicylic acid increase risk of gastrointestinal bleeding in a meta-analysis.
Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association 9, 762-768.e6 [PubMed:21699808]
[show Abstract]
Deng L, Hu S, Baydoun AR, Chen J, Chen X, Cong X (2009)
Aspirin induces apoptosis in mesenchymal stem cells requiring Wnt/beta-catenin pathway.
Cell proliferation 42, 721-730 [PubMed:19706045]
[show Abstract]
Byrns MC, Penning TM (2009)
Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs.
Chemico-biological interactions 178, 221-227 [PubMed:19010312]
[show Abstract]
Anavekar NS, Murphy JG (2009)
Aspirin and infective endocarditis: an ancient medicine used to fight an ancient disease-but does it work?
The Journal of infection 58, 329-331 [PubMed:19386367]
Strong R, Miller RA, Astle CM, Floyd RA, Flurkey K, Hensley KL, Javors MA, Leeuwenburgh C, Nelson JF, Ongini E, Nadon NL, Warner HR, Harrison DE (2008)
Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice.
Aging cell 7, 641-650 [PubMed:18631321]
[show Abstract]
Watson HG, Chee YL (2008)
Aspirin and other antiplatelet drugs in the prevention of venous thromboembolism.
Blood reviews 22, 107-116 [PubMed:18226435]
[show Abstract]
García-Heredia JM, Hervás M, De la Rosa MA, Navarro JA (2008)
Acetylsalicylic acid induces programmed cell death in Arabidopsis cell cultures.
Planta 228, 89-97 [PubMed:18335236]
[show Abstract]
Huang ZW, Luo Y, Wu Z, Tao Z, Jones RO, Zhao HB (2005)
Paradoxical enhancement of active cochlear mechanics in long-term administration of salicylate.
Journal of neurophysiology 93, 2053-2061 [PubMed:15590729]
[show Abstract]
Witte KK, Clark AL (2004)
The effect of aspirin on the ventilatory response to exercise in chronic heart failure.
European journal of heart failure 6, 745-748 [PubMed:15542410]
[show Abstract]
Streck RD, Kumpf SW, Ozolins TR, Stedman DB (2003)
Rat embryos express transcripts for cyclooxygenase-1 and carbonic anhydrase-4, but not for cyclooxygenase-2, during organogenesis.
Birth defects research. Part B, Developmental and reproductive toxicology 68, 57-69 [PubMed:12852484]
[show Abstract]
Kutuk O, Basaga H (2003)
Aspirin prevents apoptosis and NF-kappaB activation induced by H2O2 in hela cells.
Free radical research 37, 1267-1276 [PubMed:14753751]
[show Abstract]
Bazzi MD, Rabbani N, Duhaiman AS (2002)
Inhibition of camel lens zeta-crystallin by aspirin and aspirin-like analgesics.
The international journal of biochemistry & cell biology 34, 70-77 [PubMed:11733186]
[show Abstract]
Sexton RC (2001)
Aspirin in cardiovascular disease.
Tennessee medicine : journal of the Tennessee Medical Association 94, 208-210 [PubMed:11402787]
[show Abstract]
Schröder A, Levin RM, Kogan BA, Longhurst PA (2001)
Aspirin treatment improves bladder function after outlet obstruction in rabbits.
Urology 58, 608-613 [PubMed:11597554]
[show Abstract]
Epelde F, Garca-Castrillo Riesgo L, Loma-Osorio A, Verdier J, Recuerda Martnez E (2000)
[The use of acetylsalicylic acid in patients with ischemic cardiomyopathy cared for in Spanish emergency services (results of the EVICURE Study). Evaluacion del Manejo de la cardiopatia isquemica en los Servicios de Urgencias Hospitalarios of the Sociedad Espanola de Medicina de Urgencias y Emergencias (SEMES)].
Medicina clinica 115, 455-457 [PubMed:11203441]
[show Abstract]
Varga JM, Kalchschmid G, Klein GF, Fritsch P (1991)
Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody.
Molecular immunology 28, 641-654 [PubMed:1650428]
[show Abstract]
Warrington RJ, Tse KS (1979)
Lymphocyte transformation studies in drug hypersensitivity.
Canadian Medical Association journal 120, 1089-1094 [PubMed:445303]
[show Abstract]
Last Modified
20 September 2021