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]]>2-(1-piperidyl)ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate
Flavoxate is an acetylcholine antagonist. It is a muscarinic antagonist.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 391.5 g/mol |
2 | Physical appearance | Solid |
3 | Melting point | 246-248 |
4 | Solubility | 10 mg/ml |
5 | Octanol/water partition coefficient | 2.1 |
6 | Presence of ring | Chromine, benzene and piperidine |
7 | Number of chiral centers | Not present |
Flavoxate acts as a direct antagonist for the muscarinic acetylcholine receptors. It reduces the tonus of smooth muscles in the bladder and thus, reduces the frequent urge for micturition.
i. 1-(2-hydroxyphenyl)propan-1-one undergoes nitration in presence of methyl iodide to give 1-(2-methoxy-3-nitrophenyl propan-1-one.
ii. It then undergoes reduction to produce 1-(3-amino-2-methoxyphenyl) propan-1-one.
iii. On reeaction with nitrous acid followed by reaction with copper cyanide, 2-methoxy-3-propionylbenzonitrile is produced.
iv. Treatment with aluminium chloride produces 2-hydroxy-3-propionylbenzonitrile.
v. The above formed compound on reaction with benzylchloride in presence of sodium benzoate produces 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carbonitrile.
vi. The latter compound on reduction and followed by reaction with SOCl2 and 2-(piperidin-1-yl)ethanol, produces flavoxate.
Flavoxate is used for:
Side effects of flavoxate are:
Q.1 Correct statements related to the physicochemical properties of drug flavoxate are?
I. Molecular weight: 391.5 gm/mol
II. Present in solid form.
III. Octanol/water partition coefficient is 5.4
IV. Five chiral carbon atoms are present in structure
a) I, II
b) I II, III
c) II, IV
d) II, IV
Q.2 Match the following of the drugs with their correct IUPAC names.
i. Flavoxate | A. 2-(1-piperidyl)ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate |
ii. Eszopiclone | B. 7-Chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one |
iii. Chlordiazepoxide | C. 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide |
iv. Lorazepam | D. (S)-(+)-6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl-4-methyl-1-piperazinecarboxylate |
a) i-B, ii-C, iii-A, iv-D
b) i-D, ii-A, iii-B, iv-C
c) i-A, ii-B, iii-C, iv-D
d) i-A, ii-D, iii-C, iv-B
Q.3 Correct steps for the mechanism of action of the drug Flavoxate?
I. Antogonizes muscarinic acetylcholine receptors
II. Antagonizes nicotinic acetylcholine receptors
III. Decreases the tonus of smooth muscles in the bladder
IV. Increases the tonus of smooth muscles in the bladder
a) I – III
b) I – IV
c) II – III
d) II – IV
Q.4 Correct sequence for True/false for the classification of the drug can be?
a) TTFT
b) FFTT
c) FTFT
d) TFTT
Q.5 Maximum potency obtained of flavoxate when the distance between the ring substituted carbons is how many carbon units.
a) 1
b) 2
c) 3
d) 4
Q.6 Types of ring structure present in flavoxate?
I. Chromine
II.Benzine
III. Piperidine
IV. Pyrrolopyrimidine
a) I, II, III, IV
b) III, IV
c) I, III
d) I, II, III
Q.7 Side effect of drug Flavoxate?
a) Dizziness
b) Constipation
c) Blurred vision
d) All of the above
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1-a
2-d
3-a
4-c
5-b
6-d
7-d
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