Aspirin
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)
General
Type : Salicylic, Acetate, Benzoate, Drug, Antiplatelet
Chemical_Nomenclature : 2-acetyloxybenzoic acid
Canonical SMILES : CC(=O)OC1=CC=CC=C1C(=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)
InChIKey : BSYNRYMUTXBXSQ-UHFFFAOYSA-N
Other name(s) : Acetylsalicylic acid || 2-Acetoxybenzoic acid || Ecotrin || Acenterine || Acetosal || 2-(Acetyloxy)benzoic acid || salicylic acid acetate
MW : 180.2
Formula : C9H8O4
CAS_number : 50-78-02
PubChem : 2244
UniChem : BSYNRYMUTXBXSQ-UHFFFAOYSA-N
IUPHAR : 4139
Wikipedia : Aspirin
Target
Structures : No structure
Families : BCHE, Carb_B_Chordata
References (13)
| Title : Vicagrel enhances aspirin-induced inhibition of both platelet aggregation and thrombus formation in rodents due to its decreased metabolic inactivation - Jia_2019_Biomed.Pharmacother_115_108906 |
| Author(s) : Jia YM , Ge PX , Zhou H , Ji JZ , Tai T , Gu TT , Zhu T , Li YF , Mi QY , Huang BB , Xie HG |
| Ref : Biomed Pharmacother , 115 :108906 , 2019 |
| Abstract : |
| PubMedSearch : Jia_2019_Biomed.Pharmacother_115_108906 |
| PubMedID: 31060007 |
| Title : Aspirin Attenuates the Bioactivation of and Platelet Response to Vicagrel in Mice - Jia_2018_J.Cardiovasc.Pharmacol_72_252 |
| Author(s) : Jia YM , Gu TT , Ji JZ , Tai T , Zhang MR , Huang BB , Zhou H , Mi QY , Xie HG |
| Ref : J Cardiovasc Pharmacol , 72 :252 , 2018 |
| Abstract : |
| PubMedSearch : Jia_2018_J.Cardiovasc.Pharmacol_72_252 |
| PubMedID: 30358688 |
| Title : Aspirin Hydrolysis in Plasma Is a Variable Function of Butyrylcholinesterase and Platelet-activating Factor Acetylhydrolase 1b2 (PAFAH1b2) - Zhou_2013_J.Biol.Chem_288_11940 |
| Author(s) : Zhou G , Marathe GK , Hartiala J , Hazen SL , Allayee H , Tang WH , McIntyre TM |
| Ref : Journal of Biological Chemistry , 288 :11940 , 2013 |
| Abstract : |
| PubMedSearch : Zhou_2013_J.Biol.Chem_288_11940 |
| PubMedID: 23508960 |
| Title : Reaction of human albumin with aspirin in vitro: mass spectrometric identification of acetylated lysines 199, 402, 519, and 545 - Liyasova_2010_Biochem.Pharmacol_79_784 |
| Author(s) : Liyasova MS , Schopfer LM , Lockridge O |
| Ref : Biochemical Pharmacology , 79 :784 , 2010 |
| Abstract : |
| PubMedSearch : Liyasova_2010_Biochem.Pharmacol_79_784 |
| PubMedID: 19836360 |
| Title : Serum aspirin esterase is strongly associated with glucose and lipids in healthy subjects: different association patterns in subjects with type 2 diabetes mellitus - Kotani_2010_Diabetol.Metab.Syndr_2_50 |
| Author(s) : Kotani K , Kimura S , Ebara T , Caccavello R , Gugliucci A |
| Ref : Diabetol Metab Syndr , 2 :50 , 2010 |
| Abstract : |
| PubMedSearch : Kotani_2010_Diabetol.Metab.Syndr_2_50 |
| PubMedID: 20659351 |
| Title : Discovery of a true aspirin prodrug - Moriarty_2008_J.Med.Chem_51_7991 |
| Author(s) : Moriarty LM , Lally MN , Carolan CG , Jones M , Clancy JM , Gilmer JF |
| Ref : Journal of Medicinal Chemistry , 51 :7991 , 2008 |
| Abstract : |
| PubMedSearch : Moriarty_2008_J.Med.Chem_51_7991 |
| PubMedID: 19049433 |
| Title : Evaluation of nitrate-substituted pseudocholine esters of aspirin as potential nitro-aspirins - Gilmer_2007_Bioorg.Med.Chem.Lett_17_3217 |
| Author(s) : Gilmer JF , Moriarty LM , Clancy JM |
| Ref : Bioorganic & Medicinal Chemistry Lett , 17 :3217 , 2007 |
| Abstract : |
| PubMedSearch : Gilmer_2007_Bioorg.Med.Chem.Lett_17_3217 |
| PubMedID: 17376682 |
| Title : Isosorbide-based aspirin prodrugs. II. Hydrolysis kinetics of isosorbide diaspirinate - Gilmer_2002_Eur.J.Pharm.Sci_16_297 |
| Author(s) : Gilmer JF , Moriarty LM , Lally MN , Clancy JM |
| Ref : Eur J Pharm Sci , 16 :297 , 2002 |
| Abstract : |
| PubMedSearch : Gilmer_2002_Eur.J.Pharm.Sci_16_297 |
| PubMedID: 12208460 |
| Title : Synthesis, hydrolysis kinetics and anti-platelet effects of isosorbide mononitrate derivatives of aspirin - Gilmer_2001_Eur.J.Pharm.Sci_14_221 |
| Author(s) : Gilmer JF , Moriarty LM , McCafferty DF , Clancy JM |
| Ref : Eur J Pharm Sci , 14 :221 , 2001 |
| Abstract : |
| PubMedSearch : Gilmer_2001_Eur.J.Pharm.Sci_14_221 |
| PubMedID: 11576827 |
| Title : Butyrylcholinesterase-catalysed hydrolysis of aspirin, a negatively charged ester, and aspirin-related neutral esters - Masson_1998_Biochim.Biophys.Acta_1387_41 |
| Author(s) : Masson P , Froment MT , Fortier PL , Visicchio JE , Bartels CF , Lockridge O |
| Ref : Biochimica & Biophysica Acta , 1387 :41 , 1998 |
| Abstract : |
| PubMedSearch : Masson_1998_Biochim.Biophys.Acta_1387_41 |
| PubMedID: 9748494 |
| Title : Sex differences in the enzymatic hydrolysis of acetylsalicylic acid by microsomes from various rat tissues - Vargas_1997_J.Appl.Toxicol_17_347 |
| Author(s) : Vargas Loza AM , Montes de Oca EI , Posadas del Rio FA |
| Ref : Journal of Applied Toxicology , 17 :347 , 1997 |
| Abstract : |
| PubMedSearch : Vargas_1997_J.Appl.Toxicol_17_347 |
| PubMedID: 9418940 |
| Title : Genetic variants of human serum cholinesterase influence metabolism of the muscle relaxant succinylcholine. - Lockridge_1990_Pharmacol.Ther_47_35 |
| Author(s) : Lockridge O |
| Ref : Pharmacol Ther , 47 :35 , 1990 |
| Abstract : |
| PubMedSearch : Lockridge_1990_Pharmacol.Ther_47_35 |
| PubMedID: 2195556 |
| Gene_locus related to this paper: human-BCHE |
| Title : Prediction of drug sensitivity in individuals with atypical serum cholinesterase based on in vitro biochemical studies - Valentino_1981_Biochem.Pharmacol_30_1643 |
| Author(s) : Valentino RJ , Lockridge O , Eckerson HW , La Du BN |
| Ref : Biochemical Pharmacology , 30 :1643 , 1981 |
| Abstract : |
| PubMedSearch : Valentino_1981_Biochem.Pharmacol_30_1643 |
| PubMedID: 7271851 |