SKU: R040

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Description

Rifampicin sodium (Rifampin) is a semisynthetic antimicrobial compound derived from rifamycin SV and originally developed by the Lepetit group in 1965.  Rifampicin shows activity against gram-positive bacteria, particularly mycobacteria like tuberculosis, some gram-negative anaerobic bacteria, protozoa, fungi, and poxviruses.

Rifampicin sodium inhibits the assembly of DNA and protein into mature virus particles. It inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase, which results in cell death.

Rifampicin sodium has been shown to inhibit α-synuclein fibrillation and disaggregate fibrils in a concentration-dependent manner. Rifampicin can activate pregnane X receptor (PXR), which affects cytochrome P450, and the activity of glucuronosyltransferases and P-glycoprotein. Rifampicin has been shown to enhance CYP2C-mediated metabolism, affect compounds that are transported by P-glycoprotein and metabolized by CYP3A4.

Rifampicin sodium is an immunosuppressive agent.

For a safer and easier to use Rifampicin, try TOKU-E's ready-made Rifampicin Solution (10 mg/mL in water).

Synonyms: RFP, Rifampin, 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV, NIH 10782, NSC 113926

    CAS Number

    38776-75-9

    Molecular Formula

    C43H58N4NaO12

    Molecular Weight

    844.93

    Mechanism of Action

    Rifampicin sodium targets prokaryotic DNA dependent RNA polymerases which prevent subsequent RNA transcription and protein translation.

    Storage Conditions

    2-8┬░C

    Tariff Code

    2941.90.5000

    Spectrum

    Rifampicin is a broad-spectrum antibiotic with a wide range of activity including: 

    • Gram-positive aerobic bacteria, particularly Staphylococcus spp and Rhodococcus equi
    • Brucella and some other fastidious organisms are susceptible but Gram-negative bacteria more generally are resistant
    • Gram-positive and Gram-negative anaerobic bacteria are inhibited at low concentrations, including Bacteroides fragilis
    • Chlamydophila and Rickettsia are susceptible
    • Mycobacterium tuberculosis: activity is high against this organism but most other mycobacteria are resistant
    • Some protozoa
    • Some fungi and poxviruses

Applications

    Eukaryotic Cell Culture Applications

    Rifampicin has been shown to have immunosuppressive effects in mice.  There are no immunosuppressive effects in humans when rifampicin is given in doses at or below clinically recommended levels.

    Rifampicin has been shown to inhibit α-synuclein fibrillation and disaggregate fibrils in a concentration-dependent manner. Rifampicin can activate pregnane X receptor (PXR), which affects cytochrome P450, and the activity of glucuronosyltransferases and P-glycoprotein. Rifampicin has been shown to enhance CYP2C-mediated metabolism, affect compounds that are transported by P-glycoprotein and metabolized by CYP3A4.

    Microbiology Applications

    Rifampicin sodium is commonly used in bacterial recombinant protein expression to inhibit bacterial RNA polymerase activity and synthesis of host bacterial proteins. Rifampicin sodium can also be used as a selective agent to isolate Campylobacter jejuni.

    Plant Biology Applications

    Rifampicin has been tested in Jerusalem artichoke tuber explants by adding 10 to 50 µg/ml to the tissue culture medium. At 50 µg/ml no bacterial infection was detectable, without affecting cell division rates, cytodifferentiation and DNA synthesis. As a result Rifampicin was used as antibacterial in the following experiments of this university department (Philips, 1981).

    Rifampicin is a selective inhibitor of chloroplast RNA polymerase and can be used to study chloroplast-level DNA transcription in plants.

Specifications

    Form

    Powder

    Appearance

    Fine or slightly granular red powder

    Impurity Profile

    Rifampicin B: Not more than 0.5% Rifampicin S: Not more than 2.0% Other: Not more than 2.0%

    Water Content (Karl Fischer)

    12.0 - 17.0%

    Absorbance

    190 - 210

    pH

    4.5 - 8.0

    Assay

    Not less than 900 IU/mg

    Heavy Metals

    Not more than 10 ppm

References

    References

    "Rifampin: Mechanisms of Action and Resistance." Oxford Journals (1983): n. pag. Clinical Infectious Diseases. Web. 21 Aug. 2012.

    "Philips R., Arnott S.M. and K aplan S.E., 1981, Antibiotics in plant tissue culture: rifampicin effectively controls bacterial contaminants without affecting the growth of short-term explant cultures of Helianthus tuberosus. Plant Science Letters, 21 (1981) 235-240.

    Li, T., & Chiang, J. Y. (2006). Rifampicin induction of CYP3A4 requires pregnane X receptor cross talk with hepatocyte nuclear factor 4alpha and coactivators, and suppression of small heterodimer partner gene expression. Drug metabolism and disposition: the biological fate of chemicals34(5), 756-64.

    Jill E Maddison, A David J Watson, Jonathan Elliott (2008) Chapter 8 - Antibacterial drugs, Small Animal Clinical Pharmacology (Second Edition), 148-185.

    Bassi, L., Berardino, L., Arioli, V., Silvestri, L., & Lignière, E. (1973). Conditions for Immunosuppression by Rifampicin. The Journal of Infectious Diseases, 128(6), 736-744. 

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