An internal standard for the quantification of rifaximin
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Unlabeled Version(s)
16131Rifaximin
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Rifaximin-d6

Item No. 26101

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-d6-1,15(2H)-dione
CAS Number
1262992-43-7
Molecular Formula
C43H45D6N3O11
Formula Weight
791.9
Purity
≥99% deuterated forms (d1-d6)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
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([2H])=C([2H])C(C([2H])([2H])[2H])=C5[2H])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/i1D3,14D,16D,18D
InChi Key
NZCRJKRKKOLAOJ-JDVCSXHWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Rifaximin-d6 is intended for use as an internal standard for the quantification of rifaximin (Item No. 16131) by GC- or LC-MS. 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 of traveler's 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).