BY: LIK HAN &
CYNTHIA Aspirin
The history of Aspirin
• Use of willow tree and
meadow sweet in ancient 1828 • German chemists
Greek and Egypt. Hermann Kolbe and
• Recommended by Eduard Lautemann
Hippocrates, the father of • German pharmacist Johann synthesized salicylic acid
medicine. Buchner identified, isolated from phenol and carbon
and purified salicylic acid. dioxide
2000BC
– 400 BC 1860
The history of Aspirin
• Felix Hoffman successfully
synthesize acetylsalicylic 1899
acid which is named by him
as Asprin.
• Friedrich Bayer, the employer
of Hoffman patented the drug
and sold it commercially,
making aspirin on of the first
pharmaceutical drugs
Acetyl group Spirea Ulmaria
1897
Uses of Aspirin
Reduce the risk of
NSAID stroke and heart
attack
anti-
analgesic antipyretic inflammatory
Mechanism of Actions in Body
Treatment fever, pain and
inflammation Treatment of heart diseases
Aspirin inhibiting the synthesis of the Through the inhibition on COX-1
cyclooxygenase isoenzymes, COX-1 & synthesis of thromboxane A2 is
COX-2. blocked
Thromboxane A2
constricts blood vessels and
COX-1 COX-2 induces platelets to form clot
responsible for the enhance
formation of inflammatory
prostaglandins (PGs) responses and
which causes the causes symptoms
perception of pain and of diseases to
fever. show up
Side Effects of Aspirin
Headache
Hearing Difficulty
Sudden Vision Change
Severe Vomiting
Yellowing skin Rene Syndrome
(for children)
Stomach Ulcer
Nausea
Serious Allergic
Reactions:
-rashes & itchiness
-breathing difficulties
Structure and Functional Groups of Aspirin
Carboxyl Group
Ester Group
Aromatic Ring
IUPAC Name:
2 – Acetyloxybenzoic acid
Synthesis of Aspirin
Reaction Pathways
Reaction Pathway #1: Kolbe Schmidt Reaction
NaOH CO2 H+
Neutralization Carboxylation Acidification
Benzenesulfonic Sodium • 140°C Sodium
acid Phenolate • 6-7 atm Salicylate
Salicylic Acid
Reaction Pathway #2: Esterification
Salicylic Acid Acetic Anhydride Acetylsalicylic acid Acetic Acid
Metabolism of Aspirin
Future New Alternatives
Buffered aspirin
- combination of antacid and aspirin
- reduce upset stomach and heartburn
Rivaroxaban
- proven more effective than aspirin in
preventing future blood clotting.
References
•Amazon.com (2018). Buffered Aspirin. Retrieved from https://www.amazon.com/Rite-Aid-Buffered-Aspirin-
Tablets/dp/B0030HTWGI
•Bayer Corporation. (2017). Picture of Felix Hoffman. Retrieved from https://www.sciencehistory.org/historical-
profile/felix-hoffmann
•Clipground. (2017). Picture of willow tree. Retrieved from http://clipground.com/willow-clipart.html
•Drug Discovery & Development (2016). BMJ Investigation Casts Doubt on Validity of Rivaroxaban Trial. Retrieved from
https://www.dddmag.com/news/2016/02/bmj-investigation-casts-doubt-validity-rivaroxaban-trial
•Feinman, S. E. (1994). Beneficial and Toxic Effects of Aspirin. Florida: CRC Press.
• Greenstein, B. & Gould, D. (1958). Trounce's Clinical Pharmacology for Nurses (17th
ed.). Philadelphia, United States of America: Churchill Livingstone.
•Healthappointmen.com (2003). Picture of Thromboxane A2. Retrieved from h
ttps://healtheappointments.com/chapter-20-blood-drugs-essays/
•Hennekens, C. H., Dyken, M. L., & Fuster, V. (1997). Aspirin as a Therapeutic Agent in
Cardiovascular Disease: A Statement for Healthcare Professionals From the American
Heart Association. Circulation, 96(8), 2751-2753.
doi:http://dx.doi.org/10.1161/01.cir.96.8.2751
• Julien, R. M. (2001). A Primer of Drug Action (9th ed.). Oregon, United States of
America: Worth Publishers.
• Liska, K. (2000). Drugs and the Human Body with Implications for Society (6th ed.). New
Jersey, Unites States of America: Prentice Hall, Inc.
• McGavock, H. (2011). How Drugs Work : Basic Pharmacology for healthcare
professionals (3rd ed.). Oxford, United Kingdom: Radcliffe Publishing Ltd.
References
•National Center for Biotechnology Information. (2018). Aspirin, CID=2244. Retrieved
from PubChem Compound Database: https://pubchem.ncbi.nlm.nih.gov/compound/aspirin#section=Top
•Olmsted, J. (1998). Synthesis of Aspirin. Journal of Chemical Education, 75(10), 1261-1263.
Retrieved from http://web.missouri.edu/~glaserr/3700s10/A01S4.pdf
•Polyvore. (2017). Picture of meadowsweet. Retrived from
https://www.polyvore.com/filipendula_ulmaria_meadowsweet_public_domain/thing?id=58350 599
• Rainsford, K. D. (2004). Aspirin and Related Drugs. London: Taylor & Francis Inc.
• Rivaroxaban more effective than aspirin for preventing blood clots, study results suggest.
(2017). The Pharmaceutical Journal. doi:10.1211/pj.2017.20202482
• Rose, P. W., Watson, E. K., & Jenkins, L. S. (2011). Aspirin for prevention of cancer and cardiovascular
disease. British Journal of General Practice, 61(587), 412- 415. doi:http://dx.doi.org/10.3399/bjgp11x578133
•Selleck Chemicals. (n.d.) Rivaroxaban Chemical Structure. Retrieved from
http://www.selleckchem.com/products/Rivaroxaban.html
• Slideplayer (n.d.). Aspirin Metabolism. Retrieved from http://slideplayer.com/slide/5857136/
• Wikipedia Commons. (2017). Picture of Johann Buchner. Retrieved from
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