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6-chloro-1,1-dioxo-2H-1,2,4-benzothiadiazine-7-sulfonamide
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 295.7 g/mol |
2 | Physical appearance | White crystalline powder |
3 | Melting point | 342.5oC |
4 | Solubility | Freely soluble in dimethylformamide; practivally insoluble in ether; soluble in water |
5 | Octanol/water partition coefficient | -0.24 |
5 | Presence of ring | Benzothiazine |
6 | Number of chiral centers | Not present |
General structure activity of thiazide diuretics can be summarized as:
i. Sulfonylchlorination of 3-chloroaniline using chlorosulfonic acid to produce 4,6-sulfonochloride-3-chloroaniline.
ii. The last is reacted with ammonia to give 4,6-sulfonylamido-3-chloroaniline.
iii. Heating of the above formed compound with formamide produces chlorothiazide drug.[2]
Chlorothiazide is used for:
Side effects of chlorothiazide are:
Q.1 What can be the correct IUPAC nomenclature of Chlorothiazide?
a) 6-chloro-1,1-dioxo-2H-1,2,4-benzothiadiazine-7-sulfonamide
b) 1,4:3,6-dianhydro-2,5-di-O-nitro-D-propanol.
c) 1-[(4-Chlorophenyl)(phenyl)methyl]-4-methylpiperazine
d) 1-[(4-Chlorophenyl)(phenyl)methyl]-4-ethyliperazine
Q.2 Which amongst the following statements is/are correct related to the SAR of thiazide diuretics?
I. Chlorothiazide is the simplest member of the series.
II. Hydrogen atom at the 2-N is most acidic due to presence of electron-withdrawing group.
III. Sulfonamide group at C-7 position provides additional acidity to the drug.
a) I, III
b) II, III
c) I, II
d) I, II, III
Q.3 The correct order for the synthesis of drug Chlorothiazide from 3-chloroaniline can be?
I. Intermolecular dehydration
II. Sulfonylchlorination
III. Reaction with ammonia
IV. Heating with formamide
a) I – IV
b) I – II
c) III – II
d) II – III – IV
Q.4 Side effects of drug Chlorothiazide is/are?
a) Headache
b) Diarrhea
c) Muscle spasms
d) All of the above
Q.5 Match the following drugs with their correct Octanol water partition coefficient-
i. Chlorothiazide | A. -0.24 |
ii. Cimetidine | B. 5.8 |
iii. Azatadine | C. 3.59 |
iv. Meclizine | D. 0.4 |
a) i-C, ii-B, iii-A, iv-D
b) i-C, ii-A, iii-D, iv-B
c) i-A, ii-D, iii-C, iv-B
d) i-A, ii-C, iii-B, iv-D
Q.6 An example of drug from class Thiazide diuretic?
a) Chlorothiazide
b) Amphetamine
c) Alprazolam
d) Isosorbide dinitrate
Q.7 The type of ring system found in the structure of drug Chlorothiazide is?
a) Dihydroopyridine
b) Benzothiazine
c) Phenyl
d) Pyrimidine
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ANSWERS
1-a
2-d
3-d
4-d
5-c
6-a
7-b
REFERENCES
[1] Lemke TL, Williams DA, editors. Foye’s principles of medicinal chemistry. Lippincott Williams & Wilkins; 2012 Jan 24. [2] Vardanyan R, Hruby V. Synthesis of essential drugs. Elsevier; 2006 Mar 10.
The post CHLOROTHIAZIDE 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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