An antibiotic and PXR agonist
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Labeled Version(s)
26101Rifaximin-d6
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Rifaximin

Item No. 16131

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,18E,28E)-25S-(acetyloxy)-5,6,21S,23R-tetrahydroxy-27S-methoxy-2,4,11,16Z,20S,22R,24R,26R-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione
CAS Number
80621-81-4
Synonyms
  • L 105SV
  • Rifamycin L 105
Molecular Formula
C43H51N3O11
Formula Weight
785.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
219, 238, 294, 373, 458 nm
SMILES
OC1=C(NC(/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)/C=C/O[C@@](C2=O)(C)O3)=O)C4=C(N=C5N4C=CC(C)=C5)C6=C2C3=C(C)C(O)=C61
InChi Code
InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
InChi Key
NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Rifaximin is an antibiotic derived from rifamycin SV (Item No. 21441) that inhibits the growth of a variety of Gram-positive and Gram-negative bacteria in vitro, including Staphylococcus, Streptococcus, Enterococcus, H. influenzae, and N. gonorrhoeae (MIC50s = ≤0.015, <0.12, 0.25-2, 0.25, and 0.25 μg/mL, respectively).1 It is a pregnane X receptor (PXR) agonist (EC50 = ~20 μM) that reduces colonic damage, rectal bleeding, and diarrhea in PXR-humanized, but not wild-type or Pxr-null, mice with inflammatory bowel disease (IBD) induced by dextran sulfate sodium (DSS; Item No. 23250).2,3 Rifaximin exhibits minimal intestinal absorption after oral administration and is, therefore, effective in eliminating bacteria in the gastrointestinal system.4,5 Formulations containing rifaximin have been used in the treatment travelers' diarrhea caused by noninvasive E. coli, irritable bowel syndrome with diarrhea (IBS-D), and to reduce the risk of recurrence of overt hepatic encephalopathy.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoover, W.W., Gerlach, E.H., Hoban, D.J., et al. Antimicrobial activity and spectrum of rifaximin, a new topical rifamycin derivative. Diagn. Microbiol. Infect. Dis. 16(2), 111-118 (1993).

    2. Ma, X., Shah, Y.M., Guo, G.J., et al. Rifaximin is a gut-specific human pregnane X receptor activator. J. Pharmacol. Exp. Ther. 322(1), 391-398 (2007).

    3. Cheng, J., Shah, Y.M., Ma, X., et al. Therapeutic role of rifaximin in inflammatory bowel disease: Clinical implication of human pregnane X receptor activation. J. Pharmacol. Exp. Ther. 335(1), 32-41 (2010).

    4. Alajbegovic, S., Sanders, J.W., Atherly, D.E., et al. Effectiveness of rifaximin and fluoroquinolones in preventing travelers' diarrhea (TD): A systematic review and meta-analysis. Syst. Rev. 1:39, (2012).

    5. Song, M., and Ang, T.L. Second and third line treatment options for Helicobacter pylori eradication. World J. Gastroenterol. 20(6), 1517-1528 (2014).