Medical Chemistry

Pharmacology I. Discovery, Metabolism, and Industrial

Applications of

ASPIRIN

DrugsAny 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 habituation

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.

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 beenused 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 clottingPharmacological 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 Acid• 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 Prostaglandin Swelling

Inflammation

Headquarters: Leverkusen- GermanyPublicly traded company: ticker symbol BAYZFBayer stock2011: revenue -36 Billion Euros, 106 000 employees,

40 countries worldwideProduct List ‘Highlights’: Heroin, Aspirin, Alka-

Seltzer, Zyklon-B, Polyurethane, Prontosil, Ciproflaxin, Levitra