Rifaximin (Xifaxan)RNA synthesis inhibitor, PXR activator CAS# 80621-81-4 |
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Quality Control & MSDS
3D structure
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| Cas No. | 80621-81-4 | SDF | Download SDF |
| PubChem ID | 6436173 | Appearance | Powder |
| Formula | C43H51N3O11 | M.Wt | 785.88 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 50 mg/mL (63.62 mM) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown. | ||
| SMILES | CC1C=CC=C(C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)OC(C4=O)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)C | ||
| Standard InChIKey | NZCRJKRKKOLAOJ-XRCRFVBUSA-N | ||
| Standard InChI | 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Pregnane X receptor (PXR) agonist; antibiotic. Reduces number of colon tumors and suppresses expression of TNFα and Il-1β induced in a colon cancer, PXR-humanized mouse model. Increases apoptosis and decreased proliferation in HT-29 cells. Exhibits low gastrointestinal absorption while retaining its antibacterial activity. Active against gram-positive and gram-negative bacteria. |
Rifaximin (Xifaxan) Dilution Calculator
Rifaximin (Xifaxan) Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.2725 mL | 6.3623 mL | 12.7246 mL | 25.4492 mL | 31.8115 mL |
| 5 mM | 0.2545 mL | 1.2725 mL | 2.5449 mL | 5.0898 mL | 6.3623 mL |
| 10 mM | 0.1272 mL | 0.6362 mL | 1.2725 mL | 2.5449 mL | 3.1811 mL |
| 50 mM | 0.0254 mL | 0.1272 mL | 0.2545 mL | 0.509 mL | 0.6362 mL |
| 100 mM | 0.0127 mL | 0.0636 mL | 0.1272 mL | 0.2545 mL | 0.3181 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Rifaximin is an antibiotic that inhibits RNA synthesis and acts as a PXR (pregnane-X-receptor) activator. The compound is a derivative of rifamycin that has been shown to act strongly against Enterococcus, Streptococcus and Staphylococcus, with less activity against Enterobacteriaceae. Rifaximin has been used in a variety of gastrointestinal and intestinal epithelial cell studies.
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Activation of intestinal human pregnane X receptor protects against azoxymethane/dextran sulfate sodium-induced colon cancer.[Pubmed:25277138]
J Pharmacol Exp Ther. 2014 Dec;351(3):559-67.
The role of intestinal human pregnane X receptor (PXR) in colon cancer was determined through investigation of the chemopreventive role of rifaximin, a specific agonist of intestinal human PXR, toward azoxymethane (AOM)/dextran sulfate sodium (DSS)-induced colon cancer. Rifaximin treatment significantly decreased the number of colon tumors induced by AOM/DSS treatment in PXR-humanized mice, but not wild-type or Pxr-null mice. Additionally, rifaximin treatment markedly increased the survival rate of PXR-humanized mice, but not wild-type or Pxr-null mice. These data indicated a human PXR-dependent therapeutic chemoprevention of rifaximin toward AOM/DSS-induced colon cancer. Nuclear factor kappa-light-chain-enhancer of activated B cells-mediated inflammatory signaling was upregulated in AOM/DSS-treated mice, and inhibited by rifaximin in PXR-humanized mice. Cell proliferation and apoptosis were also modulated by rifaximin treatment in the AOM/DSS model. In vitro cell-based assays further revealed that rifaximin regulated cell apoptosis and cell cycle in a human PXR-dependent manner. These results suggested that specific activation of intestinal human PXR exhibited a chemopreventive role toward AOM/DSS-induced colon cancer by mediating anti-inflammation, antiproliferation, and proapoptotic events.
Structural elucidation of the Rifaximin Ph. Eur. Impurity H.[Pubmed:19926422]
J Pharm Biomed Anal. 2010 Mar 11;51(4):858-65.
Rifaximin, a semisynthetic, rifamycin-based non-systemic antibiotic is used in the treatment of acute and chronic gastrointestinal disorders. The aim of this study was the elucidation of the molecular structure of the 802 Dalton impurity which was found in Rifaximin industrial batches and reported with an erroneous structure in European Pharmacopoeia 6.5 (2009) [7] monograph as Rifaximin Impurity H. This impurity was isolated from Rifaximin by preparative HPLC and purified by column chromatography. The molecular structure was evidenced by means of (1)H and (13)C NMR spectroscopy, mass spectrometry and FT-IR.
Rifaximin: in vitro and in vivo antibacterial activity--a review.[Pubmed:15855749]
Chemotherapy. 2005;51 Suppl 1:67-72.
In vitro inhibitory activity of rifaximin is directed against Gram-positive and Gram-negative, aerobic and anaerobic bacteria. It is effective in the treatment of gastrointestinal infections when given orally because of the high concentration of the drug remaining in the gut lumen. Laboratory investigations have been carried out to assess the in vitro activity of rifaximin on different bacterial strains isolated from both human and domestic animals. The objective of this project is to review the in vitro and in vivo activity of rifaximin against bacterial infection with Gram-negative rods, Gram-positive rods and Gram-positive cocci and their resistance to rifaximin. The available data suggest that rifaximin is active in vitro and in vivo in the treatment of bacterial infection of adults and children.
