| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-02-24 06:00:45 -0700 |
| Update Date |
2013-02-08 17:10:55 -0700 |
| HMDB ID |
HMDB01879 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Aspirin |
| Description |
This chemical 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 & 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 (blood-thinning) effect and is used in long-term low-doses to prevent heart attacks and cancer. 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 is then 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; This chemical was also 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. 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. 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); 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 (blood- thinning) effect and is used in long-term low-doses to prevent heart attacks and cancer; 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 2-(Acetyloxy)benzoate
- 2-(Acetyloxy)benzoic acid
- 2-Acetoxybenzenecarboxylic acid
- 2-Acetoxybenzoate
- 2-Acetoxybenzoic acid
- 2-Carboxyphenyl acetate
- Acenterine
- Acetard
- Aceticyl
- Acetol
- Acetonyl
- Acetophen
- Acetosal
- Acetosalin
- Acetylin
- Acetylsalicylate
- Acetylsalicylic acid
- Acetyonyl
- Acetysal
- Acetysalicylic acid
- Acylpyrin
- Asatard
- Aspergum
- Aspirdrops
- Aspirin
- Benaspir
- Bialpirinia
- Bufferin
- Caprin
- Cardioaspirina
- Easprin
- Ecolen
- Ecotrin
- Empirin
- Endosprin
- Endydol
- O-(Acetyloxy)benzoate
- O-(Acetyloxy)benzoic acid
- O-Acetoxybenzoate
- O-Acetoxybenzoic acid
- O-Acetylsalicylic acid
- O-Carboxyphenyl acetate
- Persistin
- Pharmacin
- Polopiryna
- Premaspin
- Rheumintabletten
- Rhodine
- Salcetogen
- Saletin
- Salicylic acid acetate
- Salospir
- Solprin
- Solprin acid
- Solpyron
- Tasprin
- Temperal
- Toldex
- Triaminicin
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| Chemical Formula |
C9H8O4 |
| Average Molecular Weight |
180.1574 |
| Monoisotopic Molecular Weight |
180.042258744 |
| IUPAC Name |
2-(acetyloxy)benzoic acid |
| Traditional IUPAC Name |
aspirin |
| CAS Registry Number |
50-78-2 |
| 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 Key |
BSYNRYMUTXBXSQ-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Homomonocyclic Compounds |
| Class |
Benzoic Acid and Derivatives |
| Sub Class |
Hydroxybenzoic 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 Parent |
Salicylic Acid and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
135 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
1.19 |
HANSCH,C ET AL. (1995) |
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| Predicted Properties |
|
| Spectra |
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| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
|
| Tissue Location |
|
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Acetylsalicylic Acid Pathway |
SMP00083
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Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
26.5 +/- 1.9 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB00945  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000894 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
2157 |
| KEGG Compound ID |
C01405 |
| BioCyc ID |
Not Available |
| BiGG ID |
45400 |
| Wikipedia Link |
Aspirin |
| NuGOwiki Link |
HMDB01879 |
| Metagene Link |
HMDB01879 |
| METLIN ID |
Not Available |
| PubChem Compound |
2244 |
| PDB ID |
AIN |
| ChEBI ID |
15365 |
| References |
|---|
| Synthesis Reference |
Chen, 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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