1. Celebrex (celecoxib): Its Uses, Structures, and Mechanism of Action Susan Hong Chemistry 12 B

2. Outline I. Introduction to Celecoxib a. What is arthritis? i. Types of arthritis ii. Types of anti-inflammatory b. What is the active ingredient in Celebrex? II. Structure, Formula, and Functional Groups III. Synthesis IV. Mechanism of Action V. How is Celebrex prescribed and its uses a. Side Effects and Risk Factors VI. Summary and Conclusion VII. References

3. What is arthritis? means "inflammation of a joint" a term use to refer to conditions that can cause pain in the body's joints a chronic disease which causes pain, stiffness, swelling and loss of function in the joints can affect people of all ages

4. Types of arthritis Osteoarthritis Rheumatoid Arthritis Gout Pseudo-gout

5. http://www.medicinenet.com/images/illustrations/arthritic_joints.jpg

6. Types of anti-inflammatory Celebrex FDA issued warning was voted to stay on market FDA recommending “limited use” Vioxx FDA approved in May 1999 Recalled on 9/30/04 Twice as likely to suffer heart attacks and strokes with extended use

7. What is Celebrex? NSAIDs to relieve certain types of arthritis, acute pain in adults, painful menstrual cycles, and reduce the number of colon and growths FDA approved in 1999 First new class called “COX-2 inhibitors”

8. Tablet of Celebrex Each tablet can contain 100 mg, 200 mg, or 400 mg of celecoxib Active  Celecoxib Inactive  Croscarmellose sodium  Edible inks  Magnesium stearate  Gelatin  Lactose monohydrate  Povidone  Sodium lauryl sulfate  Titanium dioxide

9. Structure and Formula Empirical Formula: C 17 H 14 F 3 N 3 O 2 S Molecular Weight: 381. 38 g IUPAC name: 4-[5-(4- methylphenyl)-3- (trifluoromethyl)-1H- pyrazol-1yl] benzenesulfonamide Structure:

10. IR of Celebrex Soluble in ethyl acetate

11. IR of Celecoxib Amine- 3300-3500 cm-1 weak Benzene rings- 1600-2000 cm-1 weak 1450-1600 cm-1 medium

12. Synthesis

13. Mechanism endolipase arachidonic acid COX-2 NSAIDs prostaglandin steroidals

14. How is Celebrex prescribed and its uses Prescribed by a MD to patients that have symptoms of the arthritis, pain and swelling, or even menstrual cramps MD would see to it that taking Celebrex would be for the patient’s best interest

15. Side Effects and Risk Factors headache abdominal pain diarrhea nausea insomnia drowsiness stomach ulcers liver damage kidney problems fluid retention

16. Summary and Conclusion Further research and testing are in progress FDA recommends “limited use”

17. References http://www.111drugstore.comwww.111drugstore.com http://www.adrugrecall.com http://www.arthritis.about.com http://www.fda.gov http://www.healthsquare.com http://www.medicalnewstoday.com/index.php?newsid=7621 http://www.medicinenet.com/images/illustrations/arthritic_ joints.jpg http://www.medicinenet.com/images/illustrations/arthritic_ joints.jpg http://www.medsafe.govt.nz Seedher, Neelam. Soulubility Enhancement of COX-2 Inhibitors Using Various Solvent Systems. AAPS PharmSciTech. 2003; 4(3) article 33