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    UNIT-II Aminoglycosideantibiotics

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    Rendra Syani
    This document discusses aminoglycoside antibiotics. It begins by defining aminoglycosides as traditional Gram-negative antibacterial agents that contain amino-modified glycosides and inhibit protein synthesis. Examples of aminoglycoside antibiotics are provided, including streptomycin, neomycin, kanamycin, and gentamycin. The document notes that aminoglycosides display bactericidal activity against Gram-negative aerobes and some anaerobes. Adverse effects including nephrotoxicity and ototoxicity are also mentioned. The mode of action of aminoglycosides is described as binding to bacterial ribosomes and disturbing normal protein synthesis. Specific uses of some aminoglycosides are then outlined.

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    UNIT-II Aminoglycosideantibiotics

    Uploaded by

    Rendra Syani
    63 views5 pages
    This document discusses aminoglycoside antibiotics. It begins by defining aminoglycosides as traditional Gram-negative antibacterial agents that contain amino-modified glycosides and inhibit protein synthesis. Examples of aminoglycoside antibiotics are provided, including streptomycin, neomycin, kanamycin, and gentamycin. The document notes that aminoglycosides display bactericidal activity against Gram-negative aerobes and some anaerobes. Adverse effects including nephrotoxicity and ototoxicity are also mentioned. The mode of action of aminoglycosides is described as binding to bacterial ribosomes and disturbing normal protein synthesis. Specific uses of some aminoglycosides are then outlined.

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    UNIT-II_Aminoglycosideantibiotics

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    This document discusses aminoglycoside antibiotics. It begins by defining aminoglycosides as traditional Gram-negative antibacterial agents that contain amino-modified glycosides and inhibit protein synthesis. Examples of aminoglycoside antibiotics are provided, including streptomycin, neomycin, kanamycin, and gentamycin. The document notes that aminoglycosides display bactericidal activity against Gram-negative aerobes and some anaerobes. Adverse effects including nephrotoxicity and ototoxicity are also mentioned. The mode of action of aminoglycosides is described as binding to bacterial ribosomes and disturbing normal protein synthesis. Specific uses of some aminoglycosides are then outlined.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    63 views5 pages

    UNIT-II Aminoglycosideantibiotics

    Uploaded by

    Rendra Syani
    This document discusses aminoglycoside antibiotics. It begins by defining aminoglycosides as traditional Gram-negative antibacterial agents that contain amino-modified glycosides and inhibit protein synthesis. Examples of aminoglycoside antibiotics are provided, including streptomycin, neomycin, kanamycin, and gentamycin. The document notes that aminoglycosides display bactericidal activity against Gram-negative aerobes and some anaerobes. Adverse effects including nephrotoxicity and ototoxicity are also mentioned. The mode of action of aminoglycosides is described as binding to bacterial ribosomes and disturbing normal protein synthesis. Specific uses of some aminoglycosides are then outlined.

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    © All Rights Reserved
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    See discussions, stats, and author profiles for this publication at: https://www.researchgate.

    net/publication/321938027

    MEDICINAL CHEMISTRY (Aminoglycoside Antibiotics)

    Presentation · December 2017


    DOI: 10.13140/RG.2.2.19507.32801

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    Dr Sumanta Mondal
    GITAM (Deemed to be University)
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    PPH 308: MEDICINAL CHEMISTRY - II Unit: II: Aminoglycoside Antibiotics

    - Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial therapeutic


    agents that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside (sugar).
    - The term can also refer more generally to any organic molecule that contains amino-sugar substructures.
    - The aminoglycoside antibiotics contain one or more amino sugars linked to an aminocytitol ring by glycosidic
    bonds.
    - Aminoglycoside antibiotics display bactericidal activity against Gram-negative aerobes and some anaerobic
    bacilli where resistance against Gram-positive and anaerobic Gram-negative bacteria.
    - Streptomycin, the first antibiotic of this group.
    - Adverse effect: The aminoglycoside can produces severe adverse effects, which include nephrotoxity,
    ototoxicity, and neuro effects. These properties have limited the use of aminoglycoside chemotherapy to serious
    systemic indications.
    - Mode of action: The aminoglycosides exhibit bactericidal effects as a result of several phenomena. Ribosomal
    binding on 30s and 50s subunits as well as the interface produces misreading; this disturbs the normal protein
    synthesis. Cell membrane damage also plays an integral part in ensuring bacterial cell death.

     Examples of aminoglycoside antibiotics


    Name Source
    Streptomycin Streptomyces griseus
    Neomycin S. fradiae
    Kanamycin S. kanamyeleticus
    Gentamycin Micromonospora purpura
    Netilmicin Micromonospora species
    Tobramycin S. tenebrarius
    Framycetin S. decaris
    Paromomycin S. rimosus and S. paramomycinus
    Amikacin It is 1-L-(-) 4-amino-2-hydroxy butyryl kanamycin

    Lecturer Notes_Dr. S. Mondal_B. Pharm 6th Semester_GITAM (Deemed to be University) Page | 1


    E-mail: [email protected]
    PPH 308: MEDICINAL CHEMISTRY - II Unit: II: Aminoglycoside Antibiotics

     Streptomycin: It is used in the treatment of infections caused by gram-negative bacteria of particular interest
    and has a high degree of activity against P. aeruginosa, where the important causative factor is burned skin. It is
    used topically in the treatment of infected bed-sores, pyodermata, burns, and in the eye infection.

     Neomycin: It is photosensitive and its main use is in the treatment of the ear, eye, and skin infections; these
    include burns, wounds, ulcer, and infected dermatoses.

    Lecturer Notes_Dr. S. Mondal_B. Pharm 6th Semester_GITAM (Deemed to be University) Page | 2


    E-mail: [email protected]
    PPH 308: MEDICINAL CHEMISTRY - II Unit: II: Aminoglycoside Antibiotics

     Kanamycin: The kanamycins do not possess D-ribose molecule. The use of kanamycins is restricted to
    infections of the intestinal tract and to systemic infections.

     Tobramycin: Its activity is similar to gentamycin. The superior activity of tobramycin against P. aeruginosa
    may make it useful in the treatment of bacterial oesteromyelitis, and pneumonia caused by Pseudomonas species.

    Lecturer Notes_Dr. S. Mondal_B. Pharm 6th Semester_GITAM (Deemed to be University) Page | 3


    E-mail: [email protected]
    PPH 308: MEDICINAL CHEMISTRY - II Unit: II: Aminoglycoside Antibiotics

     SAR of Aminoglycoside Antibiotics


    - The aminoglycosides consist of two or more amino sugars joined in glycoside linkage to a highly substituted 1,3-
    diaminocyclo hexane (aminocyclitol), which is a centrally placed ring. The ring is a 2-deoxy streptamine in all
    aminoglycosides except streptomycin and dihydrostreptomycin, where it is streptidine. Thus,
     In kanamycin and gentamycin families, two amino sugars are attached to 2-deoxy streptamine.
     In streptomycin, two amino sugars are attached to strepidine.
     In neomycin family, there are amino sugars attached to 2-deoxy streptamine.
    - The aminoglycoside antibiotics contain two important structural features. They are amino sugar portion and
    centrally placed hexose ring, which is either 2-deoxystreptamine or streptidine.
    1. Amino sugar portion

    i. The bacterial inactivating enzymes targets C-6 and C-2 position and the substitution with methyl group at C-6
    increases the enzyme resistance.
    ii. Cleavage of 3-hydroxyl or the 4-hydroxyl or both groups does not affect the activity.

    2. Centrally placed hexose ring (aminocyclitol ring)

    i. Various modifi cations at C-1 amino group have been tested. The acylation (e.g. amikacyn) and ethylation (e.g.
    1-N-ethylsisomycin) though does not increase the activity helps to retain the antibacterial potency.
    ii. In sisomicin series, 2-hydroxylation and 5-deoxygenation result in the increased inhibition of bacterial
    inactivating enzyme systems. Thus, very few modifications of the central ring are possible, which do not violate
    the activity spectrum of aminoglycosides.

    Lecturer Notes_Dr. S. Mondal_B. Pharm 6th Semester_GITAM (Deemed to be University) Page | 4


    E-mail: [email protected]

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