Quinolone: Synthesis and Drug Profile

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Chapter: Medicinal Chemistry : Quinolone Antibacterials

Quinolone Antibacterials : i. Nalidixic acid ii. Fluoroquinolones iii. Ciprofloxacin iv. Ofloxacin v. Pefloxacin


SYNTHESIS AND DRUG PROFILE

 

i. Nalidixic acid


Properties and uses: Nalidixic acid is a white or pale yellow crystalline powder, practically insoluble in water, soluble in methylene chloride, slightly soluble in acetone, alcohol, and dilute solutions of alkali hydroxides. It is particularly effective against gram-negative bacteria that cause urinary tract infection. Nalidixic acid is biotransformed into hydroxy methyl derivative at the 7-methyl group, which is also active. A low incidence of adverse effects observed includes gastrointestinal (GI) disturbances, rashes, drowsiness, headache, and visual disturbances.

Assay: Dissolve the sample in methylene chloride and add 2-propanol and carbon dioxide-free water and pass nitrogen through the solution throughout the titration by maintaining a temperature between 15°C and 20°C and titrate against 0.1 M ethanolic sodium hydroxide. Determine the end point potentiometrically.

Dosage forms: Nalidixic acid oral suspension B.P., Nalidixic acid tablets B.P.

Synthesis


 

ii. Fluoroquinolones


Synthesis


 

iii. Ciprofloxacin


Synthesis


Properties and uses: Ciprofloxacin hydrochloride is pale yellow, crystalline in nature, slightly hygroscopic powder, soluble in water, slightly soluble in methanol, very slightly soluble in ethanol, but insoluble in acetone, ethyl acetate, and methylene chloride. It is very effective for the treatment of urinary tract infection, prostatitis, and for acute diarrhoeal disease caused by Escherichia coli, Shigella, Salmonella, and Campylobacter.

Assay: It is assayed by adopting liquid chromatography technique.

Dosage forms: Ciprofloxacin tablets B.P.

 

iv. Ofloxacin


Synthesis


Properties and uses: Ofloxacin is a pale yellow or bright yellow crystalline powder, slightly soluble in water and methanol, and soluble in glacial acetic acid and methylene chloride. It is one of the most promising newer members of the fluoroquionolone family. In this product, N-ethyl moiety has been made rigid by incorporation into a heterocyclic ring. It is useful in the treatment of genitourinary, respiratory, gastrointestinal, skin, soft tissue infections, peridonitis, and gonorrhoea.

Assay: Dissolve the sample in anhydrous acetic acid and titrate against 0.1 M perchloric acid. Determine the end point potentiometrically.

 

v. Pefloxacin


Synthesis


Properties and uses: Pefloxacin mesilate is a white powder, soluble in water, slightly soluble in alcohol, and very slightly soluble in methylene chloride, used as an antibacterial agent.

Assay: Dissolve the sample in anhydrous acetic acid, add acetic anhydride, and titrate against 0.1 M perchloric acid. Determine the end point potentiometrically.

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