NIFLUMIC ACID Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

Niflumic acid

IUPAC nomenclature

2-{[3-(trifluoromethyl)phenyl]amino}nicotinic acid

Classification

  • NSAID
  • Anthranylic acid derivatives

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 282.22 g/mol
2 Physical appearance Solid
3 Melting point 203°C
4 Solubility 19 mg/L
5 Octanol/water partition coefficient 4.43
6 Presence of ring Pyridine, phenyl
7 Number of chiral centers Not present

 

 

Mechanism of Action

Niflumic acid acts as an anti-inflammatory drug and reduces pain through:

  • Inhibition of COX-2 enzyme
  • Inhibition of phospholipase A2

 

Structure Activity Relationship

General SAR for anthranylic acid derivatives can be summarized as follows:

  • Activity decreases when substitution on anthranilic acid ring.
  • Activities due to substitution on the N-aryl ring follows the general order m > o > p.
  • For disubstitution products, activity was found to be maximum when o and m positions are substituted near to each other on the N-aryl ring.
  • Substitutions on the N-aryl ring with such groups which leads the ring to be noncoplanar with the anthranilic acid ring increases the binding of the drug and hence, increases the activity (meclofenamic acid being more active than flufenamic acid).
  • NH-moiety of the anthranilic ring is important for the activity of the drug, and replacement of NH- moiety with O, CH3, S, SO2, N-CH3 or N-COCH3 groups decreases the activity of drug.
  • Position of the acidic function is important for the activity and not the nature of acidic function.
  • Replacement of carboxylic acid function with isosteric tetrazole function has no significant effect on the activity of compound.[1]

 

Method of synthesis

Reaction of 2-aminonicotinic acid with 1-bromo-3-trifluoromethylbenzene produces Niflumic acid. [2]

Therapeutic Uses

Niflumic acid is used for:

  • Treatment of pain due to rheumatoid arthritis 

 

Side Effects

Side effects of Niflumic acid are:

  • Diarrhea
  • GI ulceration
  • Diffuse pain in abdomen
  • Nausea
  • Vomiting 

 

MCQs

Q.1 Mechanism of action of Niflumic acid is due to?

a) Inhibition of COX-1

b) Inhibition of COX-2

c) Inhibition of muscarinic receptors

d) Inhibition of nicotinic receptors

Q.2 Therapeutic use of drug Niflumic acid is/are?

a) Treatment of Pain due to rheumatoid arthritis

b) Treatment of Anemia

c) Treatment of ulceration

d) All of the above

Q.3 Which amongst the following are the correct statements with respect to the SAR of Anthranylic acid derivatives?

I. For disubstitution products, activity was found to be maximum when o and m positions are substituted near to each other on the N-aryl ring.

II. Substitutions on the N-aryl ring with such groups which leads the ring to be noncoplanar with the anthranilic acid ring increases the binding of the drug and hence, increases the activity (meclofenamic acid being more active than flufenamic acid).

III. NH-moiety of the anthranilic ring is important for the activity of the drug, and replacement of NH- moiety with O, CH3, S, SO2, N-CH3 or N-COCH3 groups decreases the activity of drug.

 a) I, II, III

b) I, II

c) I, III

d) II, III

Q.4 Number of chiral centers present in the structure of Niflumic acid is?

a) 0

b) 3

c) 1

d) 2

Q.5 Correct sequence for the True/False for the physiochemical properties of the drug Niflumic acid?

  • Molecular weight:282.22gm/mol
  • Physical appearance: Solid
  •  Melting point: 2030C
  • Octanol/water partition coefficient: 4.43

a) TFFT

b) TTTT

c) TTFF

d) FFFF

Q.6 Correct statements for the IUPAC nomenclatures of the drugs are?

I. Niflumic acid: 2-{[3-(trifluoromethyl)phenyl]amino}nicotinic acid

II. Methadone: (RS)-6-(dimethylamino)-4,4-diphenylheptan-3-one

III.  Anilridine: Ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate

IV. Desflurane: 2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane

a) I, II

b) I, II, III, IV

c) I, IV

d) I, II, III, IV 

Q.7 Match the following drugs with their correct classifications-

i. Desflurane A. NSAID
ii. Codeine B. Inhalational anesthetics
iii. Niflumic acid C. Opiate analgesics
iv. Oxybutynin D. Acetycholine antagonist

 a) i-A, ii-D, iii-B, iv-C

b) i-B, ii-A, iii-D, iv-C

c) i-B, ii-C, iii-A, iv-D

d) i-A, ii-B, iii-C, iv-D

 

For More Standard and Quality Question Bank you can Join Our Test Series Programme for GPAT, NIPER JEE, Pharmacist Recruitment Exam, Drug Inspector Recruitment Exams, PhD Entrance Exam for Pharmacy

Participate in Online FREE  GPAT  TEST: CLICK HERE

  Participate in Online FREE  Pharmacist  TEST: CLICK HERE 

Participate in Online FREE  Drug Inspector  TEST: CLICK HERE 

 

ANSWERS

1-b

2-a

3-a

4-a

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.

Leave a Reply

Your email address will not be published. Required fields are marked *

1 × two =

Designed & Developed by ThemeXpert