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

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

Nifedipine

IUPAC nomenclature

3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

 

Classification

  • Dihydropyridines
  • Calcium channel blockers

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 346.3 g/mol
2 Physical appearance Yellow crystals or powder
3 Melting point 173oC
4 Solubility 250 gm/L in acetone
5 Octanol/water partition coefficient 2.2
5 Presence of ring Dihydropyridine, phenyl
6 Number of chiral centers Not present

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Mechanism of Action

i. Nifedipine block the voltage gated L-type Ca+2 channels in the myocardial cells and vascular smooth muscles.

ii. Due to this, the entry of calcium ions during depolarization is prevented.

iii. Resulting reduced peripheral arterial vascular resistance and dilating the coronary arteries.

iv. This helps in reducing the blood pressure and increasing the oxygen supply to the heart and helps to lessen the angina.

 

Structure Activity Relationship

General structure activity of dihydropyridines calcium channel blockers can be summarized as:

  • R1 should be unsubstituted.
  • R1 should be easily detachable group.
  • Basic amino ethyl ether chain at R2 increases the potency of drug, while H/aryl group results in loss of activity of drug.
  • Substitution of R3 and R5 with alkoxy carbonyl group gives optimum activity.
  • Branching of alkyl chain of ester group decreases the activity.
  • R4 must be phenyl ring.
  • S-enantiomers are more active than R-enantiomers.

 

Method of synthesis

2 molecules of methylacetoacetate, 1 molecule of 2-benzaldehyde and and ammonia react together to give nifedipine drug. [1]

 

Medicinal Uses

Nifedipine is used for the treatment of:

  • Vasopastic angina
  • Chronic stable angina
  • Hypertension 

 

Side Effects

Side effects of Nifedipine are:

  • Dizziness
  • Weakness
  • Flushing
  • Fainting
  • Lightheadedness
  • Swelling of ankles
  • Constipation
  • Headache
  • Allergic reactions 

 

MCQs

Q.1 Mechanism of action of nifedipine includes?

a) Blockking of L-type calcium channels

b) Increasing the active reabsorption of calcium and chloride in PCT

c) Alkylation of genetic material in cell

d) Preventing of the active reabsorption of calcium and chloride in PCT

Q.2 Therapeutic use of drug nifedipine is/are?

a) Treatment of vasoprastic angina

b) Treatment of Hypertension

c) Treatment of stable angina

d) All of the above

Q.3 Which of the following statement is correct related with the SAR of dihydropyridines calcium channel blockers?

a) Branching of alkyl chain of ester group increases the activity

b) Subtitution of R3 with alkoxy group decreases the activity

c) S-enantiomers are more active than R-enantiomers

d) All of the above

Q.4 Nifedipine can be synthesized by the reaction between 2-benzaldehyde, ammonia and?

a) Methylacetoacetate

b) 3,5-disulfonamido-5-trifluoromethylaniline

c) Amyl alcohol

d) Propanone

Q.5 Correct sequence for the True/False for the physiochemical properties of the drug nifedipine can be?

I. Molecular weight = 346.3 gm/mol

II. Physical appearance = Colorless to yellowish liquid

III. Melting point = 173 oC

a) TFT

b) FFT

c) FFF

d) TTT

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

I. Nifedipine: 3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

II. Pentoprazole: (RS)-6-(Difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo[d]imidazole

III. Buclizine: (RS)-1-[(4-chlorophenyl)- phenyl-methyl]-4- [(4-tert-butylphenyl) methyl] piperazine

IV. Cimetidine: 1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

a) I, II, III, IV

b) III, IV

c) II, III, IV

d) I, II

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

i.  Nifedipine A. Calcium channel blocker
ii. Omeprazol B. Antimetabolite
iii. Thioguanine C. Antihyperlipidemic
iv. Cholestipol D. Proton pump inhibitor

 a) i-A, ii-C, iii-D, iv-B

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

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

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

 

 

 

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ANSWERS

1-a

2-d

3-c

4-a

5-a

6-a

7-b

 

 

 

REFERENCES 

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

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