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

Bisoprolol

IUPAC nomenclature

(RS)-1-{4-[(2-Isopropoxyethoxy)methyl]phenoxy}-3-(isopropylamino)propan-2-ol.

 

Classification

Bisoprolol is a cardioselective ß1-adrenergic antagonist

 

Physiochemical Properties

S. NO. PHYSICAL AND CHEMICAL PROPERTIES
1 Molecular weight 325.4 g/mol
2 Physical appearance Solid
3 Melting point 100°C
4 Solubility 0.0707 mg/ml in water
5 Octanol/water partition coefficient 2.2
6 Presence of ring Benzene
7 Number of chiral centers 1

 

Mechanism of Action

  • Bisoprolol acts as an antagonist for ß1-adrenergic receptors which results in the lowering of the blood pressure through reduction in the cardiac output.
  • It also reduces the output of rennin in the kidneys
  • Bisoprolol diminishes the sympathetic nervous system output from the brain, which also reduces the blood pressure and heart rate. [1]

 

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. [2]

Method of synthesis

i. Isopropylaminopropanediol reacts with dimethylcarbonate to produce oxalidinone sulphonate.

ii. Oxalidinone sulphonate reacts with 4-hydroxybenzaldehyde to give oxalidinone benzaldehyde.

iii. Oxaldinone benzaldehyde is converted into oxalidinone benzylalcohol.

iv. Oxalidinone benzylalcohol is reacted with isopropyl oxitol to form bisoprolol.

 

Therapeutic Uses

Bisoprolol is used for treatment of:

  • High blood pressure
  • Prevention of strokes
  • Prevention of heart attacks
  • Prevention of kidney problems

 

Side Effects

Side effects of Bisoprolol are:

  • Dryness or burning of eyes
  • Nausea
  • Decreased libido
  • Anxiety
  • Dizziness
  • Tiredness
  • Weakness
  • Diarrhea
  • Slower heart rate
  • Headache
  • Cold or flu symptoms
  • Swellings
  • Allergic reactions like skin rashes
  • Breathing problems
  • Confusion
  • Sweating
  • Tremors
  • Vomiting

MCQs

Q.1 “(RS)-1-{4-[(2-Isopropoxyethoxy)methyl]phenoxy}-3-(isopropylamino)propan-2-ol” is the IUPAC nomenclature of which drug?

a) Bisprolol

b) Methysergide

c) Phentolamine

d) Carvediol

Q.2 Melting point of Bisoprolol is?

a) 250°C

b) 250°C

c) 100°C

d) 225°C

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

i. Bisoprolol A. Ergot alkaloid
ii. Methysergide B. ß2-adrenergic agonist
iii. Isoproterenol C. ß1-adrenergic antagonist
iv. Dobutamine D. ß1-adrenergic agonist

 a) i-B, ii-C, iii-A, iv-D

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

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

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

Q.4 Correct steps for the mechanism of action of the drug Bisoprolol

I. Blocking of ß1-adrenergic receptors

II. Blocking of ß2­-adrenergic receptors

III. Reduction in the cardiac output

IV. Lowering of blood pressure

a) I – III – IV

b) II – III – IV

c) III – I – IV

d) III – II – IV

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

  • Decreasing 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 less potent than aryloxyethanolamines.

a) TFFT

b)FFTT

c) FTTF

d) TTTF

Q.6 Oxalidinone benzylalcohol is reacted with isopropyl oxitol to form?

a) Amphetamine

b) Metaraminol

c) Bisoprolol

d)Oxymetazoline

 Q.7 The drug Bisoprolol is mainly used for?

a) Treatment of high blood pressure

b) Treatment of hypotension

c) Increasing the libido

d) Prevention of gonorrhea

 

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ANSWERS

1-a

2-c

3-d

4-a

5-c

6-c

7-a

  

 REFERENCES

[1] Leopold G, Ungethum W, Pabst J, Simane Z, Buhring KU, Wiemann H. Pharmacodynamic profile of bisoprolol, a new beta 1‐selective adrenoceptor antagonist. British journal of clinical pharmacology. 1986 Sep;22(3):293-300.

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

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