Flavoxate

IUPAC nomenclature

2-(1-piperidyl)ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate

Classification

Flavoxate is an acetylcholine antagonist. It is a muscarinic antagonist.

Physiochemical Properties

Mechanism of Action

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.

Structure Activity Relationship

• Either R₁ or R₂ must be heterocyclic or carbocyclic.
• The R₃ group can be hydrogen, hydroxyl, hydroxymethyl or amide.
• Most potent derivatives has X as an ester.
• X can also be either oxygen or absent completely.
• The N substituent can be quaternary ammonium salt or tertiary amine or both with different alkyl groups.
• Maximum potency obtained when the distance between the ring substituted carbons is 2 carbon units.

Method of synthesis

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.

Therapeutic Uses

Flavoxate is used for:

• Help in reducing the leakage of urine
• Reducing the feeling to urinate right away
• Reducing the conditions of frequent trips to bathroom
• Bladder pain

Side Effects

Side effects of flavoxate are:

• Dry mouth
• Vomiting
• Headache
• Dizziness
• Constipation
• Blurred vision
• Nervousness
• Nausea
• Drowsiness

MCQ

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.

 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?

• Flavoxate: Nicotinic acetylcholine antagonist
• Aszopiclone: nonbenzodiazepine sedative-hypnotic
• Chlordiazepoxide: Muscarinic acetylcholine antagonist
• Lorazepam: Benzodiazepine sedative hypnotic

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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ANSWERS

1-a

2-d

3-a

4-c

5-b

6-d

7-d