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COX.pptx
1.
© Ramaiah University
of Applied Sciences 1 Faculty of Pharmacy COX-1 AND COX-2 INHIBITORS Presenting by, Mr. Purushotham K N Asst.professor Dept. of Pharm. Chemistry SACCP. ACU 2021-2022
2.
© Ramaiah University
of Applied Sciences 2 Cyclooxygenase (COX) is an enzyme that forms prostaglandins, prostacyclins, and thromboxanes—substances called prostanoids that are responsible for the inflammatory response. COX is known as a rate-limiting enzyme because it serves as the major pathway or key for the formation of these prostanoids.
3.
© Ramaiah University
of Applied Sciences 3 Faculty of Pharmacy Cyclooxygenases (COX-1 and COX-2) are key enzymes in the conversion of arachidonic acid to prostaglandins and other lipid mediators. Because it can be induced by inflammatory stimuli, COX- 2 has been classically considered as the most appropriate target for anti-inflammatory drugs. siologic functions
4.
© Ramaiah University
of Applied Sciences 4 Faculty of Pharmacy • There are actually two forms of the cyclooxygenase enzyme: COX-1 and COX-2. Both are involved in inflammation, but only COX-1 has a beneficial effect on the body as well. • COX- 1 is known to be present in most of the tissues in your body. In the gastrointestinal tract, COX-1 maintains the normal lining of the stomach and intestines, protecting the stomach from the digestive juices.The enzyme is also involved in kidney and platelet function. • COX-2, on the other hand, is primarily found at sites of inflammation
5.
© Ramaiah University
of Applied Sciences 5 Faculty of Pharmacy • COX 1 inhibitor is a non-steroidal anti-inflammatory drug that inhibits cyclooxygenase-1 enzyme expressed constitutively in most tissues while COX 2 inhibitor is a non-steroidal anti-inflammatory drug that inhibits cyclooxygenase-2 enzyme expressed in areas of inflammation. • Non-steroidal anti-inflammatory drugs (NSAIDS) usually provide anti- inflammatory, analgesic, and antipyretic effects. They are used in the treatment of a variety of diseases. Non-steroidal anti-inflammatory drugs inhibit a particular rate-limiting enzyme called cyclooxygenase (COX) involved in the production of prostaglandins. Two isoforms of this enzyme have been identified: COX 1 and COX 2. • COX 1 inhibitor and COX 2 inhibitor are two non-steroidal anti-inflammatory drugs involved in the inhibition of cyclooxygenase 1 (COX 1) and cyclooxygenase 2 (COX 2), respectively.
6.
© Ramaiah University
of Applied Sciences 6
7.
© Ramaiah University
of Applied Sciences 7 Faculty of Pharmacy Aryl and Heteroarylacetic Acids Classification • indene/indoles, • pyrroles • oxazoles
8.
© Ramaiah University
of Applied Sciences 8 Faculty of Pharmacy Indene and Indole Acetic Acids Indomethacin Structure
9.
© Ramaiah University
of Applied Sciences 9 Faculty of Pharmacy Synthesis of Indomethacin
10.
© Ramaiah University
of Applied Sciences 10 Faculty of Pharmacy Indene and Indole Acetic Acids Sulindac Structure
11.
© Ramaiah University
of Applied Sciences 11 Faculty of Pharmacy Ketolorac
12.
© Ramaiah University
of Applied Sciences 12 Anthtranilates (fenamates)
13.
© Ramaiah University
of Applied Sciences 13 Faculty of Pharmacy Mefenamic Acid
14.
© Ramaiah University
of Applied Sciences 14 Faculty of Pharmacy Meclofenamic Acid
15.
© Ramaiah University
of Applied Sciences 15 ©M. S. Ramaiah University of Applied Sciences 15
16.
© Ramaiah University
of Applied Sciences 16 Faculty of Pharmacy Oxicams (“Enol Acids”) • Oxicams (Piroxicam and Meloxicam) are characterized by the 4- hydroxybenzothiazine heterocycle. • The acidity of the oxicams is attributed to the 4-OH with the enolate anion being stabilized by intramolecular hydrogen-bonding to the amide N-H group. • These compounds are acidic (pKa = 6.3).
17.
© Ramaiah University
of Applied Sciences 17 Faculty of Pharmacy Oxicams (“Enol Acids”) • The oxicams are primarily ionized at physiologic pH and acidity is required for COX inhibitory activity. • Examples include Piroxicam and Meloxicam
18.
© Ramaiah University
of Applied Sciences 18 Faculty of Pharmacy Piroxicam
19.
© Ramaiah University
of Applied Sciences 19 Faculty of Pharmacy Meloxicam
20.
© Ramaiah University
of Applied Sciences 20 Faculty of Pharmacy Phenylpyrazolones Pyrazole • Simply double unsaturated compound containing 2 N’s and 3 C’s in the ring with the nitrogen atoms neighbouring
21.
© Ramaiah University
of Applied Sciences 21 Phenylpyrazolones Pyrazole – Reduction products Pyrazoline Pyrazolidine
22.
© Ramaiah University
of Applied Sciences 22 Pyrazoline Substitution Products 5 – Pyrazolone 3,5-pyrazolidinedione
23.
© Ramaiah University
of Applied Sciences 23 Faculty of Pharmacy Phenylpyrazolones Phenylbutazone
24.
© Ramaiah University
of Applied Sciences 24 Faculty of Pharmacy Oxyphenbutazone
25.
© Ramaiah University
of Applied Sciences 25 Faculty of Pharmacy Silphinpyrazone
26.
© Ramaiah University
of Applied Sciences 26 Faculty of Pharmacy SAR’s • Pharmacologic activity of the 3,5-pyrazolidinedione derivatives are closely related to their Acidity (the Acidic H at 4-position). The dicarbonyl functions at 3- and 5- positions enhance the acidity of the Hydrogen at the 4-position. • Eliminating the acidic proton at the 4-position abolishes anti- inflammatory activity. • Enhancing the acidity too much leads to a decrease in anti- inflammatory activity while other effects like uricosuric effects and sodium retention
27.
© Ramaiah University
of Applied Sciences 27 Faculty of Pharmacy SAR’s • A single alkyl group at the 4-position enhances anti-inflammatory with the most activity being given by the n-butyl substituent. • Substitution of the 2- phenylthioethyl group at the four position produces anti-gout drug sulphinpyrazone
28.
© Ramaiah University
of Applied Sciences 28 Faculty of Pharmacy Anilides [p-aminophenol Derivatives] • Introduced as analgesics after the discovery of the powerful antipyretic activities of aniline • The anilides are simple acetamides of aniline (Aminobenzene), which may or may not contain a 4-hydroxy or 4-alkoxy group. • Anilides do not possess the carboxylic acid functionality and therefore they are classified as neutral drugs and possess little inhibitory activity against cyclooxygenase.
29.
© Ramaiah University
of Applied Sciences 29 Faculty of Pharmacy Anilides [p-aminophenol Derivatives] • They are believed to act as scavengers of hydroperoxide radicals. • Acetanilide was first introduced and was found to be too toxic causing jaundice. • Phenacetin was withdrawn recently due to Nephrotoxicity. • Paracetamol remains the only useful member of this group (introduced in1891)
30.
© Ramaiah University
of Applied Sciences 30 Faculty of Pharmacy
31.
© Ramaiah University
of Applied Sciences 31 Faculty of Pharmacy SAR’s • Esterification of the phenolic functional groups with methyl or propyl groups produce derivatives with greater side effects than the ethyl derivative. • Substituents on the Nitrogen atom, which reduce the basicity, also reduce activity unless the substituent is metabolically labile e.g., acetyl. • Amides derived from aromatic acid e.g. N-Phenyl benzamide's (Benzanilide) are less active or even inactive
32.
© Ramaiah University
of Applied Sciences 32 Faculty of Pharmacy Synthesis of Paracetamol • Preparation of paracetamol involves treating an amine (p- aminophenol) with an acid anhydride (acetic anhydride) to form an amide (p-acetamidophenol).
33.
© Ramaiah University
of Applied Sciences 33 Faculty of Pharmacy Selective COX-2 Inhibitors • Prostaglandins that mediate inflammation, fever and pain are produced solely COX-2 (Highly inducible by inflammation) • Selective Cox – 2 inhibitors are devoid of side effects such as gastric ulcer and it does not affect the normal functioning of the platelet, uterus and renal system.
34.
© Ramaiah University
of Applied Sciences 34 Faculty of Pharmacy Celecoxib
35.
© Ramaiah University
of Applied Sciences 35 Faculty of Pharmacy Rofecoxib
36.
© Ramaiah University
of Applied Sciences 36 Faculty of Pharmacy Valdecoxib
37.
© Ramaiah University
of Applied Sciences 37 Faculty of Pharmacy Summary • The non-steroidal anti-inflammatory drugs (NSAIDs) are widely used for the treatment of minor pain and for the management of edema and tissue damage resulting from inflammatory joint disease (arthritis). • The major mechanism by which the NSAIDs elicit their therapeutic effects (antipyretic, analgesic, and antiinflammatory activities) is inhibition of prostaglandin (PG) synthesis. • Most NSAIDs are mainly COX-1 selective (e.g., aspirin, ketoprofen, indomethacin, piroxicam, sulindac).
38.
© Ramaiah University
of Applied Sciences 38 Faculty of Pharmacy THANK YOU