|Creation Date||2006-02-24 13:00:45 UTC|
|Update Date||2013-08-14 17:06:57 UTC|
|Secondary Accession Numbers||None|
|Description||Aspirin 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).|
- 2-(Acetyloxy)benzoic acid
- 2-Acetoxybenzenecarboxylic acid
- 2-Acetoxybenzoic acid
- 2-Carboxyphenyl acetate
- Acetylsalicylic acid
- Acetysalicylic acid
- O-(Acetyloxy)benzoic acid
- O-Acetoxybenzoic acid
- O-Acetylsalicylic acid
- O-Carboxyphenyl acetate
- Salicylic acid acetate
- Solprin acid
|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|
|Super Class||Aromatic Homomonocyclic Compounds|
|Class||Benzoic Acid and Derivatives|
|Sub Class||Hydroxybenzoic Acid Derivatives|
- Organic Compounds
- Phenylacetic Acid Derivatives
- acetate ester(ChEBI)
- benzoic acids(ChEBI)
- Carboxylic Acid
- Carboxylic Acid Ester
- Dicarboxylic Acid Derivative
|Direct Parent||Salicylic Acid and Derivatives|
|Status||Detected and Quantified|
|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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- 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.
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- 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.
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- 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.
- 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.
- 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.
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- 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.
- 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.
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- 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.
- 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.
- Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4.
- Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988.
- Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30.
- 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.