Medical Chemistry Pharmacology I. Discovery, Metabolism, and Industrial Applications of ASPIRIN

Drugs Any substance that, when absorbed into the body of a living organism, alters normal bodily function. Drugs are divided into two different groups: 1.Recreational Drugs are chemical substances that affect the central nervous system, such as opioids or hallucinogens. They may be used for perceived beneficial effects on perception, consciousness, personality, and behavior. Some drugs can cause addiction and/or habituationcentral nervous systemopioidshallucinogensperceptionconsciousness personalitybehavior addiction 2.Pharmaceutical Drugs are also referred to as medicine, medication or medicament, can be loosely defined as any chemical substance intended for use in the medical diagnosis, cure, treatment, or prevention of disease.chemical substancemedical diagnosiscuretreatment preventiondisease

In this unit the word ‘drug’ always refers to pharmaceutical drugs The drug ASPIRIN is the brand name for the substance Acetyl Salicylic Acid - ASA

Acetyl Salicylic Acid Belongs to chemical substance class of organic acids Characterized by one or more carboxyl gourps: -COOH How does a carboxyl Group act as an acids?

Medical History Salicylates: chemical compound group found in willow plants (salix alba) Willow extracts have been used in all cultures through the ages for treatment of fever and pain

Acetyl Salicylic Acid Medical Effects of ASA’s Analgesic – anti pain Antipyretric – anti fever Anti-inflammatory Anti-platelet – reduces blood clotting Pharmacological Substance Class: NSAIDS – Non Steroidal Anti-Inflammatory Drugs

NSAIDS Over-the-counter drug group for the treatment of acute/chronic mild to moderate symptoms associated with colds, injuries, inflammation ASPIRIN, IBUPROFEN, MOTRIN, ALEVE, NAPROXEN …. Opposite to prescription drugs like Steroids (PREDNISONE) or Opiates: (VICADINE, OXYCONTIN)

Aspirin History 1853 Charles Frédéric Gerhardt publishes the chemical synthesis of Acetyl Salicylic AcidCharles Frédéric Gerhardt 1897 Scientists at the German chemical company BAYER conduct clinical investigations on ASA 1899 BAYER obtains brand, patent and trademark rights for ASA under the name ASPIRIN 1918 main drug to combat the ‘Spanish Flue’ pandemic–some deaths are attributed to Aspirin overdosing 1919 BAYER lost rights in the WWI reparation in Versailles 1950’s decline of ASPIRIN in the wake of better NSAIDS: IBUPROFEN

Salicylic Acid: Natural Precursor Natural substance found in the bark of the willow tree Analgesic, anti-pyretric, anti-inflammatory but severe gastrointestinal pain, bleeding

ASPIRIN Synthesis: Acetylating Salicylic Acid Salicylic Acid + Acetic Anhydride → Acetyl Salicylic Acid + Acetic Acid (vinegar)

Cyclo-Oxygenases -COX Enzymes that synthesize Prostaglandins Prostaglandins: lipids that induce immune response to infection/injury: fever, increased blood flow (swelling) reduced blood clotting, white blood cell infiltration NSAIDS temporarily decrease COX activity

Prostaglandin Metabolic Pathway

NSAIDS reduce COX Enzyme Acitivity NSAID (Aspirin) Fever COX Pain Arachidonic Acid P rostaglandinSwelling Inflammation

Headquarters: Leverkusen- Germany Publicly traded company: ticker symbol BAYZF Bayer stock 2011: revenue -36 Billion Euros, employees, 40 countries worldwide Product List ‘Highlights’: Heroin, Aspirin, Alka- Seltzer, Zyklon-B, Polyurethane, Prontosil, Ciproflaxin, Levitra