The post AZATHIOPRINE Synthesis, SAR, MCQ,Structure and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
]]>IUPAC nomenclature
6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
Azathioprine falls under the category of purine antagonist antimetabolite. It is also an immunosuppressive agent.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 277.27 g/mol |
2 | Appearance | Pale yellow crystalline powder |
3 | Melting point | 243.5 °C |
4 | Solubility | Insoluble in water. Soluble in dilute alkali solutions. |
5 | Octanol water partition coefficient | 0.1 |
6 | Presence of ring | Purine ring system |
i. Azathioprine inhibits the synthesis of purine in the cell.
ii. This will further leads to the inhibition of synthesis of DNA and RNA.
iii. Azathioprine also interacts with cellular metabolism and results in the inhibition of mitosis. [1]
i. Methanamine is reacted with diethyl oxalate in the presence of ethylhydroxide at room temperature to form N,N’- dimethyloxalamide.
ii. N,N’-dimethyloxalamide is then treated with PCl5 to give 5-chloro-1-methyl-1H-imidazol.
iii. The formed compound undergoes nitration reaction to produce5-chloro-1-methyl-4-nitro-1H-imidazol.
iv. It is then treated with 9H-purine-8-thiol to finally produce Azathioprine.
It is given for the Treatment of
Q.1 What can be the correct IUPAC nomenclature of the drug Azathioprine
a) 6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
b) 1,1′,1′′-Phosphorothioyltriaziridine
c) 4-[bis(2-chlorethyl)amino]benzenebutanoic acid
d) 3,7-dihydropurine-6-thione
Q.2 Which amongst the following statements is/are INCORRECT related to the SAR of Azathioprine?
I. Activity of the drug increases with decrease in the carbon chain length.
II. Substitution at the 2nd position can increase the activity of the drug irrespective to the type of substituent.
III. Introduction of the lipophillic group at the 6th position will increase the activity of the drug.
a) II & III
b) I & II
c) I, II & III
d) Only II
Q.3 The correct order for the mechanism of action of Azathioprine can be?
I. DNA and RNA synthesis are inhibited
II. Inhibition of purine synthesis
III. Inhibition of pyrimidine synthesis
IV. Cytotoxicity of cell
a) I-III-IV
b) I-II-IV
c) III-I-IV
d) II-I-IV
Q.4 The drug Azathioprine is mainly used for?
a) Treatment of skin cancers
b) As an immunosuppressant
c) Treatment of diabetes
d) Treatment of mouth sores
Q.5 Match the drugs with the correct classification.
i. 5-Flourouracil | A. Purine antagonist antimetabolite |
ii. Azathioprine | B. Pyrimidine antagonst antimetabolite |
iii. Methotrexate | C. Folate antagonist antimetabolie |
iv. Anastrozol | D. Aromatase inhibitor |
a) i-C, ii-D, iii-A, iv-B
b) i-D, ii-C, iii-A, iv-B
c) i-A, ii-B, iii-D, iv-C
d) i-B, ii-A, iii-C, iv-D
Q.6 How many statements below are true with respect to the side effects of the drug Azathioprine?
a) 3
b) 1
c) 4
d) 2
Q.7 The type of ring system found in Azathioprine is?
a) Pyrimidine ring system
b) Purine ring system
c) Pteridine ring system
d) Both b) and c)
1-a
2-c
3-d
4-b
5-d
6-a
7-c
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