PROPANTHELINE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses

Propantheline

IUPAC nomenclature

Methyl-di(propan-2-yl)-[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium

Classification

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

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 368.5 g/mol
2 Physical appearance Solid
3 Melting point 152-162°C
4 Solubility Very soluble in water
5 Presence of ring Xanthenes
6 Number of chiral centers Not present
 

 

Mechanism of Action

Propantheline reduces the effect of acetylcholine by blocking the receptors for acetylcholine on smooth muscles. It’s effects also includes the direct relaxation of the smooth muscles. [1]

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. Xanthene-9-carboxylic acid chloride reacts with 2-diisopropylaminoethanol.

ii. Alkylation of the formed compound using methyl bromide gives propantheline.

 

Therapeutic Uses

Propantheline is used for:

  • Reducing muscle spasms
  • Treatment of peptic ulcers

 

Side Effects

Side effects of propantheline are:

  • Constipation
  • Nausea
  • Vomiting
  • Widened pupil
  • Blurred vision
  • Dizziness
  • Decreased sweating
  • Dry mouth

 

MCQ

Q.1 “Methyl-di(propan-2-yl)-[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium” is the IUPAC nomenclature of which drug?

a) Trihexyphenidyl

b) Propantheline

c) Oxybutynin

d) Oxazepam

Q.2 Melting point of Propantheline is?

a) 152-162°C

b) 129-130°C

c) 205.5°C

d) 258.5°C

Q.3 Match the following with correct classifications of the drugs.

i. Propantheline A. Benzodiazepine sedative-hypnotic
ii. Oxazepam B. Barbiturate
iii. Clozapine C. Muscarinic antagonist
iv. Thiamylal D. Benzpines

 a) i-A, ii-C, iii-D, iv-B

b) i-C, ii-A, iii-D, iv-B

c) i-A, ii-B, iii-D, iv-C

d) i-C, ii-B, iii-A, iv-D

Q.4 Mechanism of action of Propantheline is based on?

a) Blocking the Muscarinic acetylcholine receptors

b) Blocking the nicotinic acetylcholine receptors

c) Direct relaxation of smooth muscles

d) Both a) and c)

Q.5   Correct sequence for True and False for the given statements related with the SAR of drug trihexyphenidyl

  • Either R1 or R2 must be heterocyclic or carbocyclic.
  • The R3 group can be hydrogen, hydroxyl, hydroxymethyl or amide..
  • 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.

a) TFTF

b) FTFT

c) TTTT

d)FFTF

Q.6 Steps involved in the synthesis of Propantheline from xanthenes-9-carboxylic acid chloride in the correct sequence is?

I. Reaction with 2-diisopropylaminoethanol

II. Grignard’s reaction with cyclohexylmagnesium chloride

III. Alkylation using methylbromide

a) I – II – III

b) I – III

c) I – II

d) II – I – III

Q.7 The drug Propantheline is mainly used for?

a) Parkinson’s disease

b) Muscle spasm

c) Depression

d) Constipation 

 

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ANSWERS

1-b

2-a

3-b

4-d

5-c

6-b

7-b

  

REFERENCES

[1] Blaivas JG, Labib KB, Michalik SJ, Zayed AA. Cystometric response to propantheline in detrusor hyperreflexia: therapeutic implications. The Journal of urology. 1980 Aug;124(2):259-62.

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