Record Information
Version3.6
Creation Date2006-02-24 13:00:45 UTC
Update Date2013-08-14 17:06:57 UTC
HMDB IDHMDB01879
Secondary Accession NumbersNone
Metabolite Identification
Common NameAspirin
DescriptionAspirin is only found in individuals who have consumed this drug. Aspirin or acetylsalicylic acid (acetosal) is a drug in the family of salicylates, often used as an analgesic (against minor pains and aches), antipyretic (against fever), and anti-inflammatory. It has also an anticoagulant effect and is used in long-term low-doses to prevent heart attacks and cancer. It was isolated from meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839. While their extract was somewhat effective, it also caused digestive problems such as irritated stomach and diarrhoea, and even death when consumed in high doses. In 1853, a French chemist named Charles Frederic Gerhardt neutralized salicylic acid by buffering it with sodium (sodium salicylate) and acetyl chloride, creating acetosalicylic anhydride. Gerhardt's product worked, but he had no desire to market it and abandoned his discovery. In 1897, researcher Arthur Eichengrun and Felix Hoffmann, a research assistant at Friedrich Bayer & Co. in Germany, derivatized one of the hydroxyl functional groups in salicylic acid with an acetyl group (forming the acetyl ester), which greatly reduced the negative effects. This was the first synthetic drug, not a copy of something that existed in nature, and the start of the pharmaceuticals industry. The name 'aspirin' is composed of a- (from the acetyl group) -spir- (from the plant genus Spiraea) and -in (a common ending for drugs at the time). It has also been stated that the name originated by another means. As referring to AcetylSalicylic and 'pir' in reference to one of the scientists who was able to isolate it in crystalline form, Raffaele Piria. Finally 'in' due to the same reasons as stated above. Salicylic acid (which is a naturally occurring substance found in many plants) can be acetylated using acetic anhydride, yielding aspirin and acetic acid as a byproduct. It is a common experiment performed in organic chemistry labs, and generally tends to produce low yields due to the relative difficulty of its extraction from an aqueous state. The trick to getting the reaction to work is to acidify with phosphoric acid and heat the reagents under reflux with a boiling water bath for between 40 minutes and an hour. Aspirin 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).
Structure
Thumb
Synonyms
  1. 2-(Acetyloxy)benzoate
  2. 2-(Acetyloxy)benzoic acid
  3. 2-Acetoxybenzenecarboxylic acid
  4. 2-Acetoxybenzoate
  5. 2-Acetoxybenzoic acid
  6. 2-Carboxyphenyl acetate
  7. Acenterine
  8. Acetard
  9. Aceticyl
  10. Acetol
  11. Acetonyl
  12. Acetophen
  13. Acetosal
  14. Acetosalin
  15. Acetylin
  16. Acetylsalicylate
  17. Acetylsalicylic acid
  18. Acetyonyl
  19. Acetysal
  20. Acetysalicylic acid
  21. Acylpyrin
  22. Asatard
  23. Aspergum
  24. Aspirdrops
  25. Aspirin
  26. Benaspir
  27. Bialpirinia
  28. Bufferin
  29. Caprin
  30. Cardioaspirina
  31. Easprin
  32. Ecolen
  33. Ecotrin
  34. Empirin
  35. Endosprin
  36. Endydol
  37. O-(Acetyloxy)benzoate
  38. O-(Acetyloxy)benzoic acid
  39. O-Acetoxybenzoate
  40. O-Acetoxybenzoic acid
  41. O-Acetylsalicylic acid
  42. O-Carboxyphenyl acetate
  43. Persistin
  44. Pharmacin
  45. Polopiryna
  46. Premaspin
  47. Rheumintabletten
  48. Rhodine
  49. Salcetogen
  50. Saletin
  51. Salicylic acid acetate
  52. Salospir
  53. Solprin
  54. Solprin acid
  55. Solpyron
  56. Tasprin
  57. Temperal
  58. Toldex
  59. Triaminicin
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name2-(acetyloxy)benzoic acid
Traditional IUPAC Nameaspirin
CAS Registry Number50-78-2
SMILES
CC(=O)OC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChI KeyBSYNRYMUTXBXSQ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzoic Acid and Derivatives
Sub ClassHydroxybenzoic Acid Derivatives
Other Descriptors
  • Organic Compounds
  • Phenylacetic Acid Derivatives
  • acetate ester(ChEBI)
  • benzoic acids(ChEBI)
Substituents
  • Benzoyl
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
Direct ParentSalicylic Acid and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.19HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.46 g/LALOGPS
logP1.43ALOGPS
logP1.24ChemAxon
logS-2.1ALOGPS
pKa (strongest acidic)3.41ChemAxon
pKa (strongest basic)-7.1ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area63.6ChemAxon
rotatable bond count3ChemAxon
refractivity44.45ChemAxon
polarizability16.8ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue Location
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Acetylsalicylic Acid PathwaySMP00083Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified26.5 +/- 1.9 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00945
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000894
KNApSAcK IDNot Available
Chemspider ID2157
KEGG Compound IDC01405
BioCyc IDNot Available
BiGG ID45400
Wikipedia LinkAspirin
NuGOwiki LinkHMDB01879
Metagene LinkHMDB01879
METLIN IDNot Available
PubChem Compound2244
PDB IDAIN
ChEBI ID15365
References
Synthesis ReferenceChen, Hong; Long, Xiang; Huang, Siqing. Synthesis of aspirin with vitamin C as catalyst. Huaxue Shijie (2004), 45(12), 642-643.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Markuszewski L, Rosiak M, Golanski J, Rysz J, Spychalska M, Watala C: Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin? Basic Clin Pharmacol Toxicol. 2006 May;98(5):503-9. Pubmed: 16635110
  2. Frelinger AL 3rd, Furman MI, Linden MD, Li Y, Fox ML, Barnard MR, Michelson AD: Residual arachidonic acid-induced platelet activation via an adenosine diphosphate-dependent but cyclooxygenase-1- and cyclooxygenase-2-independent pathway: a 700-patient study of aspirin resistance. Circulation. 2006 Jun 27;113(25):2888-96. Epub 2006 Jun 19. Pubmed: 16785341
  3. Eikelboom JW, Hankey GJ, Thom J, Claxton A, Yi Q, Gilmore G, Staton J, Barden A, Norman PE: Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial. J Thromb Haemost. 2005 Dec;3(12):2649-55. Pubmed: 16359503
  4. Eikelboom J, Feldman M, Mehta SR, Michelson AD, Oates JA, Topol E: Aspirin resistance and its implications in clinical practice. MedGenMed. 2005 Jul 11;7(3):76. Pubmed: 16369302
  5. Konrad CJ, Schuepfer GK, Gerber H, Rukwied R, Schmelz M, Schley M: Duration of effects of aspirin on platelet function in healthy volunteers: an analysis using the PFA-100. J Clin Anesth. 2006 Feb;18(1):12-7. Pubmed: 16517326
  6. Faraday N, Becker DM, Yanek LR, Herrera-Galeano JE, Segal JB, Moy TF, Bray PF, Becker LC: Relation between atherosclerosis risk factors and aspirin resistance in a primary prevention population. Am J Cardiol. 2006 Sep 15;98(6):774-9. Epub 2006 Jul 28. Pubmed: 16950183
  7. Lee SH, Rhim T, Choi YS, Min JW, Kim SH, Cho SY, Paik YK, Park CS: Complement C3a and C4a increased in plasma of patients with aspirin-induced asthma. Am J Respir Crit Care Med. 2006 Feb 15;173(4):370-8. Epub 2005 Nov 17. Pubmed: 16293803
  8. Perneby C, Wallen NH, Rooney C, Fitzgerald D, Hjemdahl P: Dose- and time-dependent antiplatelet effects of aspirin. Thromb Haemost. 2006 Apr;95(4):652-8. Pubmed: 16601836
  9. Maree AO, Curtin RJ, Chubb A, Dolan C, Cox D, O'Brien J, Crean P, Shields DC, Fitzgerald DJ: Cyclooxygenase-1 haplotype modulates platelet response to aspirin. J Thromb Haemost. 2005 Oct;3(10):2340-5. Epub 2005 Sep 9. Pubmed: 16150050
  10. Satoh K, Ozaki Y: [Attempts for aspirin monitoring with a new assay system, Ultegra Rapid Platelet Function Assay (RPFA), based on turbidimetric platelet agglutination of whole blood samples] Rinsho Byori. 2006 Jun;54(6):576-82. Pubmed: 16872006
  11. Cornelissen J, Kirtland S, Lim E, Goddard M, Bellm S, Sheridan K, Large S, Vuylsteke A: Biological efficacy of low against medium dose aspirin regimen after coronary surgery: analysis of platelet function. Thromb Haemost. 2006 Mar;95(3):476-82. Pubmed: 16525576
  12. Eliasson B, Cederholm J, Nilsson P, Gudbjornsdottir S: The gap between guidelines and reality: Type 2 diabetes in a National Diabetes Register 1996-2003. Diabet Med. 2005 Oct;22(10):1420-6. Pubmed: 16176206
  13. Zailaie MZ: Aspirin reduces serum anti-melanocyte antibodies and soluble interleukin-2 receptors in vitiligo patients. Saudi Med J. 2005 Jul;26(7):1085-91. Pubmed: 16047057
  14. Aktas B, Pozgajova M, Bergmeier W, Sunnarborg S, Offermanns S, Lee D, Wagner DD, Nieswandt B: Aspirin induces platelet receptor shedding via ADAM17 (TACE). J Biol Chem. 2005 Dec 2;280(48):39716-22. Epub 2005 Sep 22. Pubmed: 16179345
  15. Maree AO, Curtin RJ, Dooley M, Conroy RM, Crean P, Cox D, Fitzgerald DJ: Platelet response to low-dose enteric-coated aspirin in patients with stable cardiovascular disease. J Am Coll Cardiol. 2005 Oct 4;46(7):1258-63. Pubmed: 16198840
  16. Lev EI, Patel RT, Maresh KJ, Guthikonda S, Granada J, DeLao T, Bray PF, Kleiman NS: Aspirin and clopidogrel drug response in patients undergoing percutaneous coronary intervention: the role of dual drug resistance. J Am Coll Cardiol. 2006 Jan 3;47(1):27-33. Epub 2005 Dec 9. Pubmed: 16386660
  17. Sun W, Gerhardinger C, Dagher Z, Hoehn T, Lorenzi M: Aspirin at low-intermediate concentrations protects retinal vessels in experimental diabetic retinopathy through non-platelet-mediated effects. Diabetes. 2005 Dec;54(12):3418-26. Pubmed: 16306357
  18. Tantry US, Bliden KP, Gurbel PA: Overestimation of platelet aspirin resistance detection by thrombelastograph platelet mapping and validation by conventional aggregometry using arachidonic acid stimulation. J Am Coll Cardiol. 2005 Nov 1;46(9):1705-9. Epub 2005 Oct 10. Pubmed: 16256872
  19. Hermida RC, Ayala DE, Calvo C, Lopez JE, Mojon A, Rodriguez M, Fernandez JR: Differing administration time-dependent effects of aspirin on blood pressure in dipper and non-dipper hypertensives. Hypertension. 2005 Oct;46(4):1060-8. Epub 2005 Aug 8. Pubmed: 16087788
  20. Savion N, Varon D: Impact--the cone and plate(let) analyzer: testing platelet function and anti-platelet drug response. Pathophysiol Haemost Thromb. 2006;35(1-2):83-8. Pubmed: 16855351
  21. Randomised trial of intravenous streptokinase, oral aspirin, both, or neither among 17,187 cases of suspected acute myocardial infarction: ISIS-2. ISIS-2 (Second International Study of Infarct Survival) Collaborative Group. Lancet. 1988 Aug 13;2(8607):349-60. Pubmed: 2899772
  22. Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. Pubmed: 11124191
  23. Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. Pubmed: 12411346
  24. Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. Pubmed: 12484694
  25. Dorsch MP, Lee JS, Lynch DR, Dunn SP, Rodgers JE, Schwartz T, Colby E, Montague D, Smyth SS: Aspirin resistance in patients with stable coronary artery disease with and without a history of myocardial infarction. Ann Pharmacother. 2007 May;41(5):737-41. Epub 2007 Apr 24. Pubmed: 17456544

Enzymes

Gene Name:
AKR1C1
Uniprot ID:
Q04828
Gene Name:
PTGS2
Uniprot ID:
P35354
Gene Name:
PTGS1
Uniprot ID:
P23219
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2C8
Uniprot ID:
P10632

Transporters

Gene Name:
ABCB1
Uniprot ID:
P08183
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694