Aspirin

By Ina Kmpf J.W.Goethe University of Frankfurt

Content
What is Aspirin History of Aspirin Indications Synthesis of Aspirin Mechanism of action Common-side effects Conclusion and Literature

What is Aspirin
Aspirin is an analgesic

the brand name Aspirin was coined by the Bayer company of Germany also called acetylsalicylic acid
C9H8O4

most frequently selled acetylsalicylic acid compound worldwide

History of aspirin
in the 5 th century people used the bitter powder extracted from a willow bark to relieve pain

salicylic acid was used since 1874 as a drug

willow bark

History of aspirin
in 1897 Felix Hofmann formed acetylsalicylic acid by derivatizing one of the hydroxyl functional groups in salicylic acid with an acetyl group
Felix Hofmann

'Aspirin' was patented in 1899

Indications
local analgetic effect antipyretic anti-inflammatory antiplatelet

Synthesis of Aspirin
O OH
CO2 NaOH phenol salicylic acid

ONa ONa
H2SO4

OH OH

Kolbe-Schmitt reaction
named after Adolph Wilhelm Hermann Kolbe and Rudolf Schmitt carboxylation chemical reaction that proceeds by heating sodium phenolate with carbon dioxide under pressure, then treating the product with sulfuric acid. The final product is an aromatic hydroxy acid which is also known as salicylic acid

Synthesis of Aspirin
COOH OH O O O CH3 COOH O CH3

H3PO4

O H3C OH

+ H3C salicylic acid

+ aspirin

acetic anhydride

acetic acid

Salicylic acid is then acetylated using acetic anhydride, yielding aspirin and acetic acid as a byproduct The original synthesis of aspirin from salicylic acid involved acetylation with acetyl chloride. The byproduct from this is hydrochloric acid, which is corrosive and environmentally hazardous

Mechanism of action
Aspirin inhibits an enzyme, called COX which is responsible for the production of prostaglandines there are two forms : COX 1 and COX 2

COX 1
continuously stimulated by the body its concentration in the body remain stable creates prostaglandins used for basic house keeping throughout body prostaglandins stimulate normal body functions such as stomach mucous production, regulation of gastric acid and kidney water excretion

COX 2
induced ( normally not present in cells) built only in special cells (A549 lung cells) used for signaling pain and inflammation produces prostaglandins for inflammatory response stimulated only as part of immune response

Cyclooxygenase
COOH

COX1 HO Prostaglandins HO

Arachidonic Acid H

COX2

COOH

Prostaglandins H HO H Prostaglandin F2 Cyclooxygenase (COX) enzymes convert arachidonic acid (from membrane phospholipids) into cyclic prostaglandins adding oxygens (from O2) in the process Aspirin ihnibits this process by an irreversible acetylation of an amino acid from the cyclooxygenase

common-side effects
Gastrointestinal complaints (stomach upset, dyspepsia, heartburn, small blood loss) Frequently, central effects (dizziness, tinnitus, hearing loss, vertigo, centrally mediated vision disturbances, and headaches Prolonged and more severe bleeding after operations Possibility to get gastric ulcer and kidney injury

Conclusion
Aspirin is a painkiller it has an antipyretic, anti-inflammatory and antiplatelet effect synthesized from salycilic acid inhibits COX 1 and 2 => no prostaglandines

Literature
pictues: http://www.3dchem.com/imagesofmolecules/6cox.jpg http://www.3dchem.com/imagesofmolecules/Aspirin.jpg http://www.bayer.de/konzern/unternehmensgeschichte/biografien/feli x-hoffmann/page589.htm http://www.openrussia.ru/imgs/products/logos/13249.jpg text: http://de.wikipedia.org/wiki/Acetylsalicyls%C3%A4ure http://www.chm.bris.ac.uk/motm/aspirin/aspirin.htm http://en.wikipedia.org/wiki/Aspirin http://courses.chem.psu.edu/chem38/structures/aspirin/aspirin.html www.albany.edu/faculty/cs812/bio366/Cyclooxygenase_ppt.pdf http://www.chemgapedia.de/vsengine/vlu/vsc/de/ch/12/thr/vlu_thr/as pirin.vlu.html