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

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

Nicardipine

 

IUPAC nomenclature

2-[benzyl(methyl)amino]ethylmethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Classification

  • Dihydropyridines
  • Calcium channel blockers

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 479.5  g/mol
2 Physical appearance Solid
3 Melting point 136-138oC
4 Solubility 2.2 mg/L
5 Octanol/water partition coefficient 3.82
5 Presence of ring Dihydropyridine, phenyl
6 Number of chiral centers 1

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Mechanism of Action

i. Nicardipine inhibits the influx of calcium across the vascular smooth muscles and myocardial muscles cells membranes through deformation of the channel, inhibition of ion-control gating mechanism and by interfering with release of calcium ions.

ii. There is decrease in the contractile processes of the smooth muscles of myocardium.

iii. Dilation of coronary and systemic arteries, there is increase in the oxygen supply to myocardial muscles.

iv. Due to this, there is decrease in the total peripheral resistance and decrease in the systemic blood pressure and afterload.

 

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

Methyl ester of ß-aminocrotonic acid is reacted with 2-methyl-2-benzylaminoethyl ester of acetoacetic acid gives nicardipine. [1]

Medicinal Uses

Nicardipine is used for the treatment of:

  • Hypertension
  • Chronic stable angina

  

Side Effects

Side effects of Nicardipine are:

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

 

 

MCQs

Q.1 Which of the following statements are correct related with the physicochemical properties of drug Nicardipine?

I. Molecular weight: 302.11 gm/mol

II. Physical appearance: solid

III. Melting point: 136-138 oC

a) I, II, III

b) I, II

c) II, III

d) I, III

Q.2 Match the following of the drugs with their correct IUPAC names.

i. Nicardipine A. (2R)-2-{2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine
ii. Lansoprazol B. 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole
iii. Clemastine C. 2-[benzyl(methyl)amino]ethylmethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
iv. Isoxicam D. [(2R,3S)-1,3,4-trinitrooxybutan-2-yl]nitrate

 a) i-B, ii-C, iii-D, iv-A

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

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

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

Q.3 Mechanism of action of drug Nicardipine includes?

I. Inhibition of calcium influx across the vascular smooth muscles and myocardial muscles cells membranes

II. Activation of gunaylate cyclase enzyme

III. Active synthesis of cGMP

IV. Decrease in total peripheral resistance

a) I, III, IV

b) I, IV

c) II, III

d) I, II, III, IV

Q.4 Correct sequence for True/false for the classification of the drug can be?

  • Nicardipine: Organic nitrate antianginal drug
  • Carbachol: Sedative hypnotics
  • Phenytoin: Anticonvuslants
  • Desflurane: Inhalational anesthetics

a) TFFT

b) FFTT

c) FFTF

d) TTTT

Q.5 Which of the following statements related with the SAR of dihydropyridines calcium channel blockers is/are correct?

a) R1 should be unsubstituted.

b) R1 should be easily detachable group.

c) Basic amino ethyl ether chain at R2 increases the potency of drug, while H/aryl group results in loss of activity of drug.

d) All of the above

Q.6 Type of rings present in the structure of nicardipine?

I. Dihydropyridine

II. Phenyl

III. Dihydrofuran

IV. Cyclobutane

a) II, IV

b) I , II

c) III, IV

d) IV

Q.7 Side effect of drug Nicardipine is/are?

a) Dizziness

b) Headache

c) Allergic reactions

d) All of the above

 

 

 

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ANSWERS

1-c

2-c

3-b

4-b

5-d

6-b

7-d

 

 

 

REFERENCES

 

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

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