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

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


IUPAC nomenclature

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


Metipranolol is a nonselective ß-adrenergic antagonist.


Physiochemical Properties

1 Molecular weight 309.4 g/mol
2 Physical appearance Present in solid form.
3 Melting point 106°C
4 Solubility 589  mg/L
5 Octanol/water partition coefficient 2.66
6 Presence of ring Benzene
7 Number of chiral centers 1


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



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

i. Increasing side chain length A. Prevents appropriate binding of the required functional groups to the same receptors side.
ii. Aryloxypropanolamines are B. Stimulates appropriate binding of the required functional groups to the same receptors side
  C. Less potent than aryloxyethanolamines
  D. More potent than aryoxyethanolamines

 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





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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[1] [2] Lemke TL, Williams DA, Foye WO. Principles of medicinal chemistry. Williams & Wilkins; 2017, 356.

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