Chloramphenicol, 25G

SKU:
C0378-25G
  • $69.90

    • Description

    Chloramphenicol, 25 G

    ≥98% (HPLC)

    Synonym(s):
    D-(−)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide, D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide, Chloromycetin
    Linear Formula:
    Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
    CAS Number:
    56-75-7
    Molecular Weight:
    323.13
    Beilstein/REAXYS Number:
    2225532
    EC Number:
    200-287-4
    MDL number:
    MFCD00078159
    PubChem Substance ID:
    24892250
    NACRES:
    NA.76

    PROPERTIES

    assay

    ≥98% (HPLC)

    form

    powder or crystals

    pKa 

    5.5

    mp

    148-150 °C (lit.)

    antibiotic activity spectrum

    Gram-negative bacteria
    Gram-positive bacteria
    mycobacteria
    mycoplasma

    mode of action

    protein synthesis | interferes

    storage temp.

    room temp

    SMILES string

    OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O

    InChI

    1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1

    InChI key

    WIIZWVCIJKGZOK-RKDXNWHRSA-N

    Gene Information

    human ... CYP1A2(1544)

    DESCRIPTION

    General description

    Chemical structure: phenicole

    Application

    Chloramphenicol is a synthetic antibiotic, isolated from strains of Streptomyces venezuelae. It is often used for bacterial selection in molecular biology applications at 10-20μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.
    Chloramphenicol has been used as a bacteriostatic non potent antibiotic.[1] It has been used for the selection/growth of positive bacterial cells.[2][3]

    Biochem/physiol Actions

    Mode of Action: Chloramphenicol inhibits bacterial protein synthesis by blocking the peptidyl transferase step by binding to the 50S ribosomal subunit and preventing attachment of aminoacyl tRNA to the ribosome. It also inhibits mitochondrial and chloroplast protein synthesis and ribosomal formation of (p)ppGpp, de-pressing rRNA transcription.

    Mode of Resistance: Use of chloramphenicol acetyltransferase will acetylate the product and inactivate it.

    Antimicrobial Spectrum: This is a broad spectrum antibiotic against gram-positive and gram-negative bacteria, and is used mainly for ophthalmic and veterinary purposes.

    Caution

    Stock solutions should be stored at 2-8°C and are stable at 37°C for 5 days. Aqueous solutions are neutral and stable over a wide pH range, with 50% hydrolysis occurring after 290 days. Use of a borax buffered solution reduces this number to 14%. Solutions should be protected from light as photochemical decomposition results in a yellowing of the solution. Heating aqueous solutions at 115°C for 30 minutes results in a 10% loss of chloramphenicol.

    Preparation Note

    Degradation of chloramphenicol in aqueous solution is catalyzed by general acids and bases. This rate of degradation is independent of the ionic strength and pH.

    Other Notes

    Keep container tightly closed in a dry and well-ventilated place.

    SAFETY INFORMATION

    signalword

    Danger

    hcodes

    H318 - H351 - H361fd

    pcodes

    P202 - P280 - P305 + P351 + P338 - P308 + P313 - P405 - P501

    Hazard Classifications

    Carc. 2 - Eye Dam. 1 - Repr. 2

    Storage Class

    11 - Combustible Solids

    wgk_germany

    WGK 3

    ppe

    Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges