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]]>7-Chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Flurazepam is a benzodiazepine sedative-hypnotic.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 387.9 g/mol |
2 | Physical appearance | Solid; white rods from ether-petroleum ether. |
3 | Melting point | 79.5°C |
4 | Octanol/water partition coefficient | 3.8 |
5 | Solubility | Solubility of HCl salt is 500 mg/ml |
6 | Presence of ring | Diazepine, benzene |
7 | Number of chiral centers | Not present |
i. Flurazepam binds with an allosteric site on GABAA
ii. This potentiate the action of GABA on GABAA receptor through opening the chloride channel within the receptor.
iii. This results in hyperpolarisation through chloride influx.
i. Reaction of 2-amino-5-chloro-2’-flourobenzophenone (1) with bromoaetic acid chloride (2) to give 2-(bromoacetyl)amino-5-chloro-2’-flourobenzophenone (3).
ii. This on reaction with diethylamine produces 2-(diethylaminoacetyl)amino-5-chloro-2’-fluorobenzophenone (4).
iii. Reduction of both carbonyl groups of the above formed compound with lithium-aluminum hydride gives –(2’-diethylamino)ethylamino-5-chloro-2’-fluoroben-zhydrol (5).
iv. The amino group of the product is acylated by phthalimidoacetyl chloride (6) to get phthalimido derivative (7).
v. The protective group phthalimido is removed by reaction with hydrazine hydrate to get 2-(2’-diethylamino)ethylaminoacetylamino-5-hloro-2’-fluorobenzohydrol (8).
vi. On treatment of the above formed compound with hydrobromic acid will lead to intermolecular dehydration with ring closure to give a benzodiazepine cycle, 7-chloro-1-[2-(diethylamino)ethyl]-5-(2’-fluorophenyl)-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-3-one (9).
vii. Oxidation of N4-C5 bond with 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (10) gives flurazepam (11). [2]
Flurazepam is used for:
Side effects of flurazepam are:
MCQ
Q.1 Match the following with correct SAR of the drug Flurazepam-
i. An electronegative group at 7-position of the ring A | A. Increases the functional anxiolytic activity |
ii. Substitutions at 6, 8 or 9 position with electronegative group on ring A | B. Decreases the functional anxiolytic activity |
. | C. Decrease the functional anxiolytic activity |
D. Increase the functional anxiolytic activity |
a) i-A, ii-D
b) i-A, ii-C
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?
a) TFTF
b) TTFF
c) FFTT
d) TTFT
Q.3 Number of chiral carbons present in the structure of Flurazepam?
a) 0
b) 1
c) 2
d) 3
Q.4 Flurazepam drug shows its action through??
a) Agonizing the acetylcholine receptors
b) Antagonizing the muscarinic receptors
c) Binding with GABAA receptors
d) ß-inhibition
Q.5 Which amongst the following is a therapeutic use of drug flurazepam?
a) Treatment of Insomia
b) Treatment of Alzhiemer’s disease
c) Treatment of Overactive bladder
d) Treatment of Asthma
Q.6 Which of the following drug and their classification are correct?
I. Benztropin: acetylcholine antagonist
II. Fesoterodine: Nitrogen mustard
III. Flurazepam: benzodiazepine sedative hypnotic
IV. Midazolam: Acetylcholine Nicotinic receptor antagonist
a) I, III
b) I, III, IV
c) II, IV
d) I, II, III, IV
Q.7 Type of ring present in the structure of flurazepam is?
a) Diazepine ring
b) Pyrimidine
c) Pyrolopyrimidine
d) Not present
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1-a
2-b
3-a
4-c
5-a
6-a
7-a
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