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

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

Oxatomide

IUPAC nomenclature

1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-1,3-dihydro-2H-benzimidazol-2-one

Classification

  • H1-receptor antihistamine
  • Piperazine antihistamine

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 426.6 g/mol
2 Physical appearance N/A
3 Melting point 153.6oC
4 Solubility N/A
5 Octanol/water partition coefficient N/A
5 Presence of ring Piperazine, imidazolone, phenyl
6 Number of chiral centers Not present

 

Mechanism of Action

  • Oxatomide produces antagonistic effects at H1 receptors.
  • It also has antiserotonergic activity.

 

Structure Activity Relationship

Structure activity of piperizine antihistamines can be summarized as:

  • These are the derivatives of ethylene diamines.
  • The connecting moiety is CHN group
  • Primary structural difference is nature of para aromatic ring substituent
  • These are moderately potent.
  • Slow onset of action
  • Low incidence of drowsiness
  • They also exhibit peripheral and central antimuscarinic activity.

 

Method of synthesis

i. 2-benzimidazolone is reacted with 1-bromo-3-chloropropane to give 1-(3-chloropropyl)-2-benzimidazolone.

ii. The last is reacted with 1-benzhydrylpiperazine in presence of sodium carbonate to give oxatomide. [1]

Medicinal Uses

Oxatomide is used for treatment of:

  • Allergic rhinitis
  • Chronic urticaria

 

Side Effects

Side effects of Oxatomide are:

  • Drowsiness
  • Vomiting
  • Dry mouth
  • Fatigue
  • Headache
  • Difficulty in breathing
  • Swelling of face

  

MCQs

Q.1 Match the following with correct SAR of the piperizine antihistamine drugs:

i. They are derivatives of A. Ethylene diamine
ii. Connecting moiety in drug is B. Pyrimidines
  C. CHO
  D. CHN

 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?

  • Oxatomide: 1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-1,3-dihydro-2H-benzimidazol-2-one
  • Tetracaine: 2-(diphenylmethoxy)-N,N-dimethylethanamine
  • Clemastine: (2R)-2-{2-[(1R)-1-(4-chlorophenyl)-1-phenylethoxy]ethyl}-1-methylpyrrolidine
  • Methimazole: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ6,2-benzothiazine-3-carboxamide

a) TFFT

b)TFTF

c) TTTT

d) FFFT

Q.3 Molecular weight of Oxatomide is?

a) 426.6 gm/mol

b) 140.6 gm/mol

c) 361.4 gm/mol

d) 134.2 gm/mol

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

a) Anti-diabetic 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 oxatomide?

a) Chronic urticaria

b) Allergic rhinitis

c) Hay fever

d) Anticoagulant

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

I. Oxatomide: H1 receptor antihistamine drug

II. Famotdine: H2 receptor antihistamine drug

III. Pantoprazole: Proton pump inhibitor

IV. Tolbutamide: Antineoplastic drug

a) I, III

b) I, II, III, IV

c) III, IV

d) I, II, III

Q.7 1-(3-chloropropyl)-2-benzimidazolone reacts with benzhydrylpiperizine in presence of sodium carbonate to give which drug?

a) Oxatomide

b) Lasoprazole

c) Amphetamine

d) Busulfan

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ANSWERS

1-b                                                  

2-b

3-a

4-c

5-d

6-d

7-a

 

REFERENCES

[1] BE 852 405 (Janssen; appl. 14.3.1977; USA-prior. 21.12.1976, 2.4.1976).

 

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