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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
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Celebrex (celecoxib): Its Uses, Structures, and Mechanism of Action
Susan HongChemistry 12 B
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
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
Types of arthritis Osteoarthritis Rheumatoid Arthritis Gout Pseudo-gout
http://www.medicinenet.com/images/illustrations/arthritic_joints.jpg
Types of anti-inflammatoryCelebrex 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
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”
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
Structure and Formula Empirical Formula:
C17H14F3N3O2S Molecular Weight: 381. 38
g IUPAC name: 4-[5-(4-
methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1yl] benzenesulfonamide
O
NN
SNH2
O
Cl
CF3
Structure:
IR of Celebrex
Soluble in ethyl acetate
IR of Celecoxib
•Amine- 3300-3500 cm-1 weak•Benzene rings- 1600-2000 cm-1 weak 1450-1600 cm-1 medium
O
NN
SNH2
O
Cl
CF3
Synthesis
Cl
O
OO
H N
TsOH heat(-2 PrOH)
Cl
N
O
S
NHNH2
NH2
OO
-H2O-(CH3)2NH
O
NN
SNH2
O
Cl
CF3
Mechanism
CO2H
endolipase
arachidonic acid COX-2
NSAIDs
prostaglandin
steroidals
O
OH
CO2H
OH
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
Side Effects and Risk Factors headache abdominal pain diarrhea nausea insomnia drowsiness
stomach ulcers liver damage kidney problems fluid retention
Summary and Conclusion Further research and testing are in
progress FDA recommends “limited use”
References http://www.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.medsafe.govt.nz Seedher, Neelam. Soulubility Enhancement of COX-2
Inhibitors Using Various Solvent Systems. AAPS PharmSciTech. 2003; 4(3) article 33
