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]]>(RS)-1-(1-methylethylamino)-3-(1-naphthyloxy)propan-2-ol.
Propranolol is a nonselective ß-adrenergic antagonist.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 259.34 g/mol |
2 | Physical appearance | Present in solid form. |
3 | Melting point | 96°C |
4 | Solubility | 61.7 mg/L |
5 | Octanol/water partition coefficient | 3.48 |
6 | Presence of ring | Naphthalene |
7 | Number of chiral centers | 1 |
i. Propranolol blocks ß-adrenergic receptors.
ii. This leads to vasoconstriction, inhibition of angiogenic factors and basic growth factors of fibroblast, induction of apoptosis of endothelial cells and regulation of RAAS system. [1]
i. Reaction of 1-naphthol with epichlorohydrin gives 1-chloro-3-(1-naphthyloxy)-2-propanol.
ii. Latter compound is reacted with iso-propylamine to give propranolol. [3]
Propranolol is used for treatment of:
Side effects of propranolol are:
MCQs
Q.1 What can be the correct IUPAC nomenclature of Propranolol?
a) (RS)-1-(1-methylethylamino)-3-(1-naphthyloxy)propan-2-ol.
b) methyl (RS)-3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate
c) (RS)-1-{4-[(2-Isopropoxyethoxy)methyl]phenoxy}-3-(isopropylamino)propan-2-ol
d) (RS)-1-{4-[(2-Isopropoxyethoxy)methyl]phenoxybenzamide
Q.2 Which amongst the following statements is/are incorrect related to the SAR of Propranolol?
I. Increasing the chain length of the side chain prevents appropriate binding of the required functional groups to the same receptors side.
II. Side chain of aryloxypropanolamines can adopt a conformation that places the hydroxyl and amine groups into approximately the same position in space.
III. Aryloxypropalonamines permits a close overlap with the arylethanomine side chain.
a) I, III
b) II, III
c) I, II, III
d) I, II
Q.3 The correct order for the synthesis of drug propranolol from 1-naphthol can be?
I. Reaction with epichlorohydrin
II. Reaction with isopropylamine
III. Reduction
a) III – II – I
b) I – III – II
c) I – II
d) III – I
Q.4 Side effects of drug propranolol is/are?
a) Uneven heartbeats
b) Trouble breathing
c) Vision problems
d) All of the above
Q.5 Match the following drugs with their correct molecular weights-
i. Propranolol | A. 295.37 gm/mol |
ii. Esmolol | B. 309.4 gm/mol |
iii. Bisoprolol | C. 325.4 gm/mol |
iv. Metipranolol | D. 259.34 gm/mol |
a) i-B, ii-A, iii-D, iv-C
b) i-B, ii-A, iii-C, iv-D
c) i-B, ii-C, iii-A, iv-D
d) i-D, ii-A, iii-C, iv-B
Q.6 An example of drug from class Nonselective ß-adrenergic antagonist?
a) Dopamine
b) Dobutamine
c) Propranolol
d) Metaraminol
Q.7 The type of ring system found in Propranolol?
a) Naphthalene
b) Carbazoline
c) Imidazoline
d) No ring is present
1-a
2-c
3-c
4-d
5-d
6-c
7-a
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