A rifamycin antibiotic
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Active Metabolite(s)
3481725-Desacetyl Rifampicin
Labeled Version(s)
27848Rifampicin-d3
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Rifampicin

Item No. 14423

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[[(4-methyl-1-piperazinyl)imino]methyl]-rifamycin
CAS Number
13292-46-1
Synonyms
  • NIH 10782
  • NSC 113926
  • Rifampin
Molecular Formula
C43H58N4O12
Formula Weight
823.0
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH 7.2)(1:1): 0.50 mg/mlDMSO: 3.3 mg/mlEthanol: 0.12 mg/ml
λmax
236, 339, 479 nm
SMILES
OC1=C2C(C(O)=C(C)C(O[C@]3(C)O/C=C/[C@H](OC)[C@@H](C)[C@]([C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C/C=C(C)\C(N4)=O)(OC(C)=O)[H])=C2C3=O)=C(O)C4=C1/C=N/N5CCN(C)CC5
InChi Code
InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2
InChi Key
JQXXHWHPUNPDRT-SBMPKVQQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Rifampicin is a rifamycin antibiotic and inhibitor of bacterial RNA polymerase (IC50 = 0.01 μg/ml for the E. coli enzyme).1 It inhibits the growth of M. tuberculosis H37Rv in mouse peritoneal macrophages (MIC = 0.8 μg/ml) as well as clinical isolates of various species of Staphylococcus, Streptococcus, Haemophilus, and Neisseria (MICs = 0.009-1.4 μg/ml).2,3 Rifampicin increases survival in a mouse model of tuberculosis infection.3 It is also an agonist of the human pregnane X receptor (PXR; EC50 = ~2 μM).4 Formulations containing rifampicin have been used in the treatment of tuberculosis and meningococcal carriers.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wehrli, W. Rifampin: Mechanisms of action and resistance. Rev. Infect. Dis. 5(3), S407-S411 (1983).

    2. Jhamb, S.S., Goyal, A., and Singh, P.P. Determination of the activity of standard anti-tuberculosis drugs against intramacrophage Mycobacterium tuberculosis, in vitro: MGIT 960 as a viable alternative for BACTEC 460. Braz. J. Infect. Dis. 18(3), 336-340 (2014).

    3. Arioli, V., Berti, M., Carniti, G., et al. Antibacterial activity of DL 473, a new semisynthetic rifamycin derivative. J. Antibiot. (Tokyo) 34(8), 1026-1032 (1981).

    4. Gill, S.K., Xu, H., Kirchhoff, P.D., et al. Structure-based design of novel benzoxazinorifamycins with potent binding affinity to wild-type and rifampin-resistant mutant Mycobacterium tuberculosis RNA polymerases. J. Med. Chem. 55(8), 3814-3826 (2012).