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]]>7-Chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid
Clorazepate is a benzodiazepine sedative-hypnotic.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 314.72 g/mol |
2 | Physical appearance | Fine white yellow crystalline powder |
3 | Melting point | 228-235°C |
4 | Octanol/water partition coefficient | 3 |
5 | Solubility | Very soluble |
6 | Presence of ring | Benzodiazepine, benzene |
7 | Number of chiral centers | 1 |
i. Clorazepate converts into active metabolite desmethyl diazepam, which is partial agonist of GABA receptor.
ii. It binds with different receptors present in the brain and spinal cord.
iii. This increases the inhibitory effects of the GABA.
iv. Different subunits of GABA are responsible for anxiolytic, sedation, anticonvusant and anterograde amnesia effects.
i. 2-amino-5-chlorobenzonitrile reacts with phenylmagnesium bromide to give 2-amino-5-chlorobenzophenone imine.
ii. On reaction with aminomalonic ester, a heterocyclization product, 7-chloro-1,3-dihydro-3-carbethoxy-5-phenyl-2H-benzodiazepin-2-one.
iii. On hydrolysis of the above formed compound with alcoholic solution of potassium hydroxide forms a dipotassium salt of chlorazepate.
Clorazepate is used for:
Side effects of Clorazepate are:
Q.1 What can be the correct IUPAC nomenclature of Chlorazepate?
a) (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide
b) (S)-2-[3-(Diisopropylamino)-1-phenylpropyl]-4-methylphenol.
c) 7-Chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid
d) N,N-Dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide hemitartrate
Q.2 Which amongst the following statements is/are incorrect related to the SAR of Chlorazepate?
I. Ring A should include an aromatic or heteroaromatic ring for binding with 5-phenyl-1,4-benzodiazepin-2-one derivatives.
II. An electronegative group at 7-position of the ring A increases the functional anxiolytic activity.
III. Substitutions at 6, 8 or 9 position with electronegative group on ring A will increase the functional anxiolytic activity.
IV. When Heterocycles used as ring A, drug shows poor pharmacological activity.
a) I, II
b) III
c) III, IV
d) II
Q.3 Corrects sequence of the steps involved in the synthesis of Chlorazepate from 2-amino-5-chlorobenzonitrile?
I. Hydrolysis
II. Reaction with aminomalonic ester
III. Reaction with phenylmagesium bromide
a) III- II – I
b) II – I – III
c) III – I – II
d) I – III – II
Q.4 Side effects of drug Clorazepate is/are?
a) Constipation
b) Drowsiness
c) Dry mouth
d) All of the above
Q.5 Match the following drugs with their correct molecular weights-
i. Darifenacin | A.426.5 gm/mol |
ii. Tolterodine | B.307.4gm/mol |
iii. Chlorazepate | C. 325.5 gm/mol |
iv. Zolpidem | D. 314.72 gm/mol |
a) i-C, ii-B, iii-A, iv-D
b) i-C, ii-B, iii-D, iv-A
c) i-A, ii-C, iii-D, iv-B
d) i-B, ii-A, iii-D, iv-C
Q.6 An example of drug from class Bezodiazepine sedative hypnotic?
a) Methysergide
b) Chlorazepate
c) Amphetamine
d) Tolterodine
Q.7 The type of ring system found in the structure of Chlorazepate?
a) Dihydrobenzofurane
b) Pyrrolopyrimidine
c) Benzodiazepine
d) Pyrrolopyrrole ring
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1-c
2-b
3-a
4-d
5-c
6-b
7-c
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