SKU: R003  / 
    CAS Number: 13292-46-1

    Rifampicin

    $83.55 - $643.29

    Rifampicin (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 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 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 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

    Mechanism of ActionRifampicin targets prokaryotic DNA dependent RNA polymerases which prevent subsequent RNA transcription and protein translation.
    SpectrumRifampicin 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
    Impurity ProfileRelated Substances:
    Rifampicin Quinone: ≤ 1.5%
    Single Peak: ≤ 1.0%
    Sum of Peaks: ≤ 3.5%
    Microbiology ApplicationsRifampicin is commonly used in bacterial recombinant protein expression to inhibit bacterial RNA polymerase activity and synthesis of host bacterial proteins. Rifampicin can also be used as a selective agent to isolate Campylobacter jejuni.

    Rose et al. used rifampicin from TOKU-E in methacrylate-based copolymer films and studied its effects on biofilm formation: "Prevention of Biofilm Formation by Methacrylate-Based Copolymer Films Loaded With Rifampin, Clarithromycin, Doxycycline Aone or in Combination." 

    Media Supplements

    Rifampicin can be used as a selective agent in several types of isolation media:

    Campylobacter Agar - Campylobacter Selective Supplement (Preston)

    Campylobacter Agar Base - Modified Preston Campylobacter Selective Supplement

    Plant Biology ApplicationsRifampicin 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.
    Eukaryotic Cell Culture ApplicationsRifampicin 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.

    Molecular FormulaC43H58N4O12
    SourceSemi-synthetic: Amycolatopsis Rifamycinica
    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. 

    MICBacillus subtilis| 0.01 - 128|| Bacteroides fragilis| 0.0313 - >8|| Bifidobacterium adolescentis | ≥15.62|| Bifidobacterium animalis| ≥500 - ?|| Bifidobacterium bifidum| 31.25 - >500|| Bifidobacterium breve| >500|| Bifidobacterium Infantis| ≥3.9|| Bifidobacterium longum| 0.98 - 1.95|| Bifidobacterium pseudolongum| ≥125|| Bifidobacterium sp.| 0.98 - 3.9|| Bifidobacterium thermophilum| >500|| Brucella| 0.06 - 1|| Brucella melitensis| <0.125 - 32|| Brucella suis| ≥31.25|| Burkholderia cepacia| 32 - >64|| Campylobacter jejuni| ≥64|| Cellulomonas biazotea| ≥0.06|| Cellulomonas cellasea| ≤0.03|| Cellulomonas fermentans| ≥0.5|| Cellulomonas fimi| ≤0.03|| Cellulomonas flavigena| ≥0.125|| Cellulomonas gelida| ≥0.03|| Cellulomonas hominis| ≤0.03|| Cellulomonas uda| ≤0.03|| Chlamydia pneumonia| 0.005|| Chlamydia trachomatis| 0.004 - 512|| Clostridium difficile| 0.002 - 100|| Clostridium perfringens| 0.0039 - 0.016|| Clostridium spiroforme| ≥8|| Corynebacterium spp.| ≤0.015 - >2|| Diplococcus pneumoniae| 0.01 - 0.04|| Enterococcus faecalis| ≤0.015 - >128|| Enterococcus faecium| 0.0032 - >256|| Enterococcus gallinarum| 0.02 - >128|| Enterococcus spp.| ≤0.015 - >2|| Escherichia coli| 0.0008 - 16|| Fusobacterium nucleatum| 1|| Fusobacterium varium| 32|| Haemophilus influenzae| 0.04 - >2|| Helicobacter pylori| 0.125 - 8|| Jonesia denitrificans| ≤0.03|| Klebsiella pneumonia| 16|| Lactobacillus acidophilus| 0.1 - >100|| Lactobacillus gasseri| ≥0.1|| Lactobacillus johnsonii | >100|| Lactobacillus paracasei| >100|| Lactobacillus salivarius| ≥0.1|| Lactobacillus spp.| ≤0.5|| Legionella dumofii| ≤0.004 - 0.03|| Legionella longbeachae| ≤0.004|| Legionella micdadei| 0.008|| Legionella pneumophila| ≤0.004 - 0.06|| Legionella spp.| ≤0.0005 - 0.015|| Listeria spp.| 0.04 - 0.36|| Moraxella catarrhalis| <0.5 - ≤1|| Mycobacteria | 1 - 64|| Mycobacterium aurum| 0.06 - >100|| Mycobacterium bovis| ≥0.125|| Mycobacterium chelonae| ≥32|| Mycobacterium fortuitum| 8 - >32|| Mycobacterium gordonae| ≥0.25|| Mycobacterium intracellulare| 0.125 - 6.25|| Mycobacterium kansasii| 0.25 - 0.5|| Mycobacterium marinum| 0.125 - 4|| Mycobacterium microti| ≥2.5|| Mycobacterium phlei| ≥0.5|| Mycobacterium scrofulaceum| 0.06 - 2.5|| Mycobacterium smegmatis| >32 - 64|| Mycobacterium tuberculosis| 0.002 - 250|| Mycobacterium vaccae | ≥0.5|| Mycobacterium xenopi| ≥0.125|| Mycoplasma hominis| >2|| Neisseria gonorrhoeae| 0.004 - 0.5|| Neisseria spp.| 0.25 - 2|| Nocardia asteroides| 0.4 - 100|| Oerskovia turbata| ≥4|| Oerskovia xanthineolytica| ≥8|| Pediococcus acidilactici| ≥0.25|| Pseudomonas aeruginosa| ≥128|| Pseudomonas pseudomallei| 6.3 - 100|| Rhodococcus equi| 0.06 - >8|| Salmonella spp.| 16|| Salmonella typhimurium| ≥10|| Shigella flexneri| 8|| Shigella sonnei| 8 - 16|| Staphylococci| ≤0.008 - >128|| Staphylococcus aureus| ≤0.008 - 1024|| Staphylococcus capitis| ≤0.06 - >256|| Staphylococcus chromogenes | ≤0.06 - >256|| Staphylococcus epidermidis| 0.004 - >256|| Staphylococcus haemolyticus| 0.008 - >256|| Staphylococcus hominis| 0.008 - >256|| Staphylococcus saprophyticus| ≤0.06 - >256|| Staphylococcus warneri| ≤0.06 - >256|| Stenotrophomonas maltophilia| 1 - 128|| Streptococcus pneumonia| 0.03 - <0.5|| Streptococcus pyogenes| 0.031 - >8|| Streptomyces coelicolor | 0.75 - 18|| Treponema hyodysenteriae | >100|| Xylella fastidiosa| 2 - 8|| Yersinia enterocolitica| 16 - 32||