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    Cloxacillin QC

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    SeLecToR ck Lee
    Cloxacillin sodium is a penicillin antibacterial. It is synthesized from 6-aminopenicillanic acid (6-APA) and 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylic acid through an amide linkage to form cloxacillin. Cloxacillin sodium may contain impurities such as penicilloic acid of cloxacillin formed through alkali hydrolysis, 6-APA cloxacillin amide, and residual NaOH. The synthesis of cloxacillin sodium involves the reaction of HCl and SO2, and a potential impurity is N,N-dimethylaniline used to abstract HCl.

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    Cloxacillin QC

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    SeLecToR ck Lee
    181 views7 pages
    Cloxacillin sodium is a penicillin antibacterial. It is synthesized from 6-aminopenicillanic acid (6-APA) and 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylic acid through an amide linkage to form cloxacillin. Cloxacillin sodium may contain impurities such as penicilloic acid of cloxacillin formed through alkali hydrolysis, 6-APA cloxacillin amide, and residual NaOH. The synthesis of cloxacillin sodium involves the reaction of HCl and SO2, and a potential impurity is N,N-dimethylaniline used to abstract HCl.

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    Cloxacillin sodium is a penicillin antibacterial. It is synthesized from 6-aminopenicillanic acid (6-APA) and 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylic acid through an amide linkage to form cloxacillin. Cloxacillin sodium may contain impurities such as penicilloic acid of cloxacillin formed through alkali hydrolysis, 6-APA cloxacillin amide, and residual NaOH. The synthesis of cloxacillin sodium involves the reaction of HCl and SO2, and a potential impurity is N,N-dimethylaniline used to abstract HCl.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    181 views7 pages

    Cloxacillin QC

    Uploaded by

    SeLecToR ck Lee
    Cloxacillin sodium is a penicillin antibacterial. It is synthesized from 6-aminopenicillanic acid (6-APA) and 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylic acid through an amide linkage to form cloxacillin. Cloxacillin sodium may contain impurities such as penicilloic acid of cloxacillin formed through alkali hydrolysis, 6-APA cloxacillin amide, and residual NaOH. The synthesis of cloxacillin sodium involves the reaction of HCl and SO2, and a potential impurity is N,N-dimethylaniline used to abstract HCl.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 7

    Cloxacillin Sodium

    C19H17ClN3NaO5S3H2O
    MW 475.9
    Action and use:
    Penicillin antibacterial
    Cloxacillin sodium: synthesis

    Kar A. Medicinal Chemistry, 4th ed. New Delhi: New Age International;2007.
    Impurities

    3-(2-chlorophenyl)- 6-aminopenicillanic acid


    5-methylisoxazole- (6-APA)
    4-carboxylic acid

    Kar A. Medicinal Chemistry, 4th ed. New Delhi: New Age International;2007.
    Impurities

    COOH
    CH3
    Cloxacillin 6-APA H
    CH3

    N
    S
    O

    CH3 HN H

    O O O
    O
    C N
    N CH3
    HN

    H S CH3
    H
    Cl

    6-APA cloxacillin amide


    Kar A. Medicinal Chemistry, 4th ed. New Delhi: New Age International;2007.

    Impurities
    H
    CH3 COONa
    O
    O
    N CH3
    C
    Residual NaOH
    O
    CH3
    N S
    N H
    H H

    Cloxacillin Sodium
    Cl

    Penicilloic acid of Cloxacillin

    H COOH

    Alkali hydrolysis CH3 CH3

    O HN CH3
    O
    C S
    N
    HN

    H
    Cl

    Penilloic acid of Cloxacillin


    + CO2
    Synthesis

    HCl + SO2

    Vardanyan RS, Hruby VJ. Synthesis of Essential Drugs. Elsevier;2007.


    Impurities
    • N,N-Dimethylaniline:
    – To abstract HCl
    • The presence of HCl
    inhibits the synthesis
    – High boiling point
    (192-194 °C)
    • Not been fully
    elucidated Maximum 20 ppm
    – Possible
    carcinogenicity

    Choi JK, Park MK. Arch. Pharm. Res. 1981; 4(2):85-90.

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