KETOPROFEN Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

Ketoprofen

IUPAC nomenclature

(RS)-2-(3-benzoylphenyl)propanoic acid

 

Classification

  • NSAID
  • Propionic acid derivative

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 254.28 g/mol
2 Physical appearance Solid
3 Melting point 94°C
4 Solubility 51 mg/ml
5 Octanol/water partition coefficient 3.12
6 Presence of ring Phenyl
7 Number of chiral centers 1

 

Mechanism of Action

  • Ketoprofen inhibits COX-2 enzyme which results in decrease in production of prostaglandins which is responsible for conveying of pain and inflammation signals in the body.
  • It also inhibits COX-1 enzyme which is responsible for the side effects of drug like GI ulcerations.
  • Ketoprofin also have anti-bradykinin activity and lysosomal membrane-stabilization action.
  • Drug also acts on the hypothalamus and produces antipyretic effects which results in increased peripheral blood flow, vasodilation and heat dissipation.

 

Structure Activity Relationship

SAR of ketoprofen can be summarized as follows:

  • Activity decreases on placing the phenoxy group in the ortho or para position of the arylpropionic acid.
  • Replacing carbonyl group between two aromatic rigs with oxygen bridge produces another marketed analogue known as fenoprofen. [1]

 

Method of synthesis

i. 3-methylbenzophenone undergoes bromination to form 3-bromo-methylbenzophenone.

ii. Latter compound is reduced with help of sodium cyanide to give 3-cyanomethylbenzophenone.

iii. The last is reacted with diethyl ester of carbonic acid in presence of sodium ethoxide to give cyanoacetic ester derivative.

iv. On alkylation of the above formed compound by methyl iodide followed by acidic hydrolysis gives ketoprofen. [2]

 

Therapeutic Uses

Ketoprofen is used for:

  • Relieving mild to severe pain and inflammation due to arthritis

Side Effects

Side effects of Ketoprofen are:

  • Allergic reactions
  • Skin reactions
  • Shortness of breath
  • Weight gain
  • Vision changes
  • indigestion
  • Nausea
  • Jaundice
  • Pale skin
  • No urination
  • Anemia
  • Nausea
  • Vomiting
  • Nervousness
  • Diarrhea
  • Constipation
  • Dizziness
  • Headache
  • Tiredness
  • Ringing sounds in ears
  • Insomnia

 

MCQs

Q.1 Match the following with correct SAR of the class Oxicams NSAIDs-

i. On placing the phenoxy group in the ortho or para position of the arylpropionic acid A. increases the activity
ii. Replacing carbonyl group between two aromatic rigs with oxygen bridge produces another marketed analogue known as B. decreases the activity
  C. Ibuprofen
  D. Fenoprofen

 a) i-A, ii-C

b) i-A, ii-D

c) i-B, ii-C

d) i-B, ii-D

Q.2 Correct sequence for the True/False for correct IUPAC names of the drug can be?

  • Ketoprofen: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ6,2-benzothiazine-3-carboxamide
  • Fenoprofen: [2-(2,6-Dichloroanilino)phenyl]acetic acid
  • Halothane: 2-Acetoxybenzoic acid
  • Meloxicam: {(1Z)-5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1H-indene-3-yl}acetic acid

a) TFTF

b) FFFF

c) TTTT

d) TFFT

Q.3 Molecular weight of drug Ketoprofen is?

a) 351.8 gm/mol

b) 254.28 gm/mol

c) 426.21 gm/mol

d) 62.1 gm/mol

Q.4 Ketoprofen mechanism of action includes?

a) It exerts effect only on COX-2 and not on COX-1

b) It effects lead to vasoconstriction

c) It exerts effect on COX-1 and on COX-2

d) It does not produce any effect on COX

Q.5 Which amongst the following is a therapeutic use of drug Ketoprofen?

a) Treatment of bronchospasm

b) Reducing pain due to arthritis

c) Controlling vomiting

d) All of the above

Q.6 Which of the following drug and their classification are correct?

I. Ketoprofen: NSAID

II. Ketoprofen: Propionic acid derivative

III. Methoxyflurane: Inhalational anesthetics

IV. Alprazolem: ß-adrenergic blocker

a) III, IV

b) I, II, III

c) I, II, III, IV

d) II 

Q.7 Number of chiral carbons resent in the structure of ketoprofen is?

a) 5

b) 2

c) 1

d) 0

 

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ANSWERS

1-d

2-b

3-b

4-c

5-b

6-b

7-c

 

REFERENCES

[1]  Lemke TL, Williams DA, Roche VF, Zito SW. FOYE. S Principles of Medicinal Chemistry. Seventh Edition Copyright. 2013.

[2] Vardanyan R, Hruby V. Synthesis of essential drugs. Elsevier; 2006 Mar 10.

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