Cyproheptadine

IUPAC nomenclature

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

Classification

• H1-receptor antihistamine
• Piperidine derivative antihistamine drug

Physiochemical Properties

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:

 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

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ANSWERS

1-d

2-b

3-c

4-c

5-d

6-b

7-d

REFERENCES