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

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

Cyproheptadine

IUPAC nomenclature

4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine

Classification

  • H1-receptor antihistamine
  • Piperidine derivative antihistamine drug

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 287.4 g/mol
2 Physical appearance Crystals from dilute ethanol
3 Melting point 112.8oC
4 Solubility Soluble
5 Octanol/water partition coefficient 4.69
5 Presence of ring Piperidine ring
6 Number of chiral centers Not present

 

Mechanism of Action

  • Cyproheptadine antagonizes the effect of histamine HA-receptors by competing with free histamine for binding at HA-receptor sites. This helps in reducing the negative symptoms occurring due to HA-receptor binding.
  • The drug also competes with serotonin at receptor sites in smooth muscles of intestine and at other locations.
  • Cyproheptadine also stimulates the appetite by antagonistic effects of serotonin on the appetite center of the hypothalamus.

 

Structure Activity Relationship

General structure activity of first generation H1-receptors antagonist can be summarized as:

  • Ethylene chain gives maximum activity.
  • Increasing or decreasing the chain length decreases the activity of drug, but promethazine is an exception.
  • Chain may be present in saturated or unsaturated form, or sometimes a part of a ring system.
  • Diaryl substitution is essential for significant H1 receptor affinity.
  • Terminal nitrogen atom should be tertiary in nature.

 

Method of synthesis

i. Reaction of 1-methyl-4-magnesiumchloropiperidine with 5H-dibeno[a,d]cyclohepten-5-one to form a carbinol.

ii. The formed carbinol is dehydrated under acidic condition to give cyproheptadine. [1]

Medicinal Uses

Cyproheptadine is used for treatment of:

  • Allergic symptoms
  • Sneezing
  • Itching
  • Bronchial asthma attacks

 

Side Effects

Side effects of cyproheptadine are:

  • Dizziness
  • Drowsiness
  • Constipation
  • Blurred vision
  • Dry mouth
  • Trouble swallowing
  • Seizures
  • Allergic reactions

 

 

MCQs

Q.1 Match the following with correct SAR of the first generation H1 receptor antihistamine drugs:

i. Terminal nitrogen atom should be A. Secondary in nature
ii. Ethylene chain gives B. Tertiary in nature
  C. Minimum activity
  D. Maximum activity

 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?

  • Cyproheptadine: 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine
  • Lomustine: 2-(diphenylmethoxy)-N,N-dimethylethanamine
  • Lorcainide: (2R)-2-{2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine
  • Felodipine: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ6,2-benzothiazine-3-carboxamide

a) TFFT

b)TFFF

c) TTTT

d) FFFT

Q.3 Molecular weight of Cyproheptadine is?

a) 245.3 gm/mol

b) 452.0 gm/mol

c) 287.4 gm/mol

d) 46.9 gm/mol

Q.4 Along with antihistaminic property, Cyproheptadine also has?

a) Anti-metabolic activity

b) Anti-neoplastic actvity

c) Anti-serotonergic activity

d) Anti-hyperlipidemic activity

Q.5 Which amongst the following is not a therapeutic use of drug Cyproheptadine?

a) Chronic urticaria

b) Bronchial asthma attacks

c) Itching

d) Anesthetics

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

I. Cyproheptadine: Proton pump inhibitor

II. Cocaine: Local anesthetics

III. Rabeprazole: Proton pump inhibitor

IV. Amyl nitrite: Vasodilator

a) I, III

b) II, III, IV

c) III, IV

d) I, II, III

Q.7 Number of chiral carbons present in the structure of Cyproheptadine?

a) 1

b) 3

c) 4

d) 0

 

 

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 

Participate in CSIR NET JRF Mock Test

Participate GATE Mock Test

 

 

ANSWERS

1-d

2-b

3-c

4-c

5-d

6-b

7-d

 

REFERENCES

[1] 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 *

19 − three =

×
PG Diploma in Advance Clinical Research 2020
Apply now

Developed By Connect Globes