Metipranolol

IUPAC nomenclature

(RS)-4-{[-2-hydroxy-3-(isopropylamino)propyl]oxy}-2,3,6-trimethylphenyl acetate.

Classification

Metipranolol is a nonselective ß-adrenergic antagonist.

Physiochemical Properties

Mechanism of Action

• Metipranolol bind with ß-adrenergic and blocks it.
• It has weak local anesthetic and myocardial depressant activity.
• When used in ophthalmic, it reduces aqueous humor production. Aqueous humor outflow may also take place.

Structure Activity Relationship

• Increasing the chain length of the side chain prevents appropriate binding of the required functional groups to the same receptors side.
• Side chain of aryloxypropanolamines can adopt a conformation that places the hydroxyl and amine groups into approximately the same position in space.
• Aryloxypropalonamines permits a close overlap with the arylethanomine side chain.
• Aryloxypropanolamines are more potent than aryloxyethanolamines. [1]

Method of synthesis

4-hydroxy-2,3,6-trimethylphenyl acetate;  (S)-2-(chloromethyl)oxirane and propan-2-amine reacts together to produce metipranolol.

Therapeutic Uses

Metipranolol is used for treatment of:

• Glaucoma
• Ocular hypertension

Side Effects

Side effects of metipranolol are:

• Swelling and discomfort around the eyes
• Bronchospasm
• Sudden numbness and weakness
• Headache
• Confusion
• Slow heart rate
• Shortness of breath
• Weight gain
• Watering of eyes
• Blurred vision
• Insomia
• Altered sense of taste or smell

MCQs

Q.1 Match the following with correct SAR of the drug metipranolol-

 a) i-A, ii-C

b) i-A, ii-D

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?

• Metipranolol: (RS)-4-{[-2-hydroxy-3-(isopropylamino)propyl]oxy}-2,3,6-trimethylphenyl acetate.
• Esmolol: 3-(isopropylamino)propan-2-ol
• Bisprolol: (RS)-1-{4-[(2-Isopropoxyethoxy)methyl]phenoxybenzamide
• Metoprolol: (RS)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol

a) TFFT

b) TFTF

c) TTFF

d) TTFT

Q.3 Number of chiral centers present in the structure of metipranolol?

a) 0

b) 1

c) 2

d) 3

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

a) Blocking of α₁-adrenergic receptors

b) α₁-adrenergic agonism

c) ß-adrenergic antagonism

d) None of these

Q.5 Which amongst the following is not a therapeutic use of drug metipranolol?

a) Glaucoma

b) Ocular hypertension

c) Osteoporosis

d) None of these

Q.6 Which of the following drug and their classification are correct?

I. Metipranolol: nonselecvtive ß-adrenergic antagonist

II. Metoprolol: selective ß₁-adrenergic antagonist

III. Amphetamine: nonselective α-adrenergic agonist

IV. Clonidine: Mixed acting sympathomimetics

a) I, III

b) I, II

c) II, III, IV

d) I, II, III, IV

Q.7 Octanol/water partition coefficient of metipranolol is?

a) 2.66

b) 1.2

c) -5.4

d) 5.7

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ANSWERS

1-b

2-a

3-b

4-c

5-c

6-b

7-a

REFERENCES