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]]>(RS)-4-[2-(tert-Butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol.
Salbutamol is ß2-adrenergic agonist. [1]
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 239.31 g/mol |
2 | Physical appearance | Off-white to white crystalline solid |
3 | Melting point | 151°C |
4 | Solubility | 0.06M in water |
5 | Octanol/water partition coefficient | 1.4 |
6 | Presence of ring | Benzene ring present |
7 | Number of chiral centers | 1 |
i. Adenyl cyclase enzyme is stimulated through the ß-adrenergic receptors.
ii. The conversion of ATP to cyclic AMP also increases due to this.
iii. Due to raise in level of CAMP, relaxation of bronchial smooth muscles and inhibition of release mediators of immediate hypersensitivity from mast cells takes place.
R1 substitution:
R2 substitution:
R3 substitution on the aromatic ring:
i. p-hydroxybenzaldehyde and paraformaldehyde reactes to form compound (1)
ii. Compound (1) in reacts with unboiled water to ive compound (2) at weak basic conditions.
iii. Two hydroxyl under sulfuric acid catalyst is protect by propylidene.
iv. Compound (4) is obtained under ylide reagent and phase transfer catalyst effect, utilizing highly asic effect.
v. Compound (4) undergoes reflux in tert-butyl amine to carry out aminolysis ring opening reaction and to get compound (5).
vi. Hydrolysis of compound (5) in acidic conditions gives Salbutamol.
The drug is used:
Salbutamol is also used:
Common side effects of salbutamol are palpitations, headache, dry mouth, anxiety, tremors and muscle cramps.
Less common side effect of this drug are sleep disturbances, myocardial ischemia, skin problems, arrhythmias and tachycardia.
Q.1 What can be the correct IUPAC nomenclature of salbutamol?
a) 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
b) 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]- 4,5-dihydro-1H-imidazole
c) (RS)-4-[2-(tert-Butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
d) (RS)-[4-(1-Hydroxy-2-tert-butylamino-ethyl)-2-(4-methylbenzoyl)oxy-phenyl] 4-methylbenzoate
Q.2 Which amongst the following statements is/are incorrect related to the SAR of Salbutamol?
I. At least one of the groups is required at R2 which can form hydrogen bonds. And if only one group is present then it is preferred at 4’ position to retain the beta2 activity
II. 3’,4’-dihydroxy substitution at benzene ring has higher oral activity
III. Large lipophillic groups at R1 can afford compounds with alpha blocking activity
a) II
b) I, II
c) I, III
d) II, III
Q.3 Type of ring present in the structure of salbutamol?
a) Pyrimidine
b) Purine
c) Benzene
d) Aliphatic ring
Q.4 Side effects of drug Salbutamol is/are?
a) Palpitations
b) Headache
c) Anxiety
d) All of the above
Q.5 Match the following drugs with their correct molecular weights-
i. Salbutamol | A. 239.31 g/mol |
ii. Bitolterol | B. 210.27 g/mol |
iii. Naphazoline | C. 461.5 g/mol |
iv. Xylometazole | D. 244.37 g/mol |
a) i-B, ii-A, iii-D, iv-C
b) i-B, ii-A, iii-C, iv-D
c) i-D, ii-C, iii-A, iv-B
d) i-A, ii-C, iii-B, iv-D
Q.6 An example of drug from class ß2-adrenergic agonist?
a) Salbutamol
b) Clonidine
c) Prazosin
d) Norepinephrine
Q.7 Salbutamol is used for the treatment of?
a) Acute Hyperkalemia
b) Bronchospasm
c) COPD
d) All of the above
ANSWERS
1-c
2-a
3-c
4-d
5-d
6-a
7-d
REFERENCES
[1] Lemke TL, Zito SW, Roche VF, Williams DA. Essentials of Foye’s principles of medicinal chemistry. Wolters Kluwer; 2017, 340 [2] Lemke TL, Zito SW, Roche VF, Williams DA. Essentials of Foye’s principles of medicinal chemistry. Wolters Kluwer; 2017, 348-352
The post SALBUTAMOL Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
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