Rifaximin

Alias: BRN-3584528; L-105; BRN 3584528; L105; BRN3584528; L 105SV; Fatroximin; Normix; Rifacol; Rifamycin L 105; Rifaxidin; Rifaximin; Rifaxin; Ritacol; Rifaximin; trade names: RCIFAX, Rifagut; Xifaxan; Zaxine

Cat No.:V1469 Purity: ≥98%

COA Product Data Instructions for use SDS

Rifaximin (BRN-3584528; L-105SV; Fatroximin; Normix; Rifacol; Rifaxidin; Rifaxin; Ritacol; Rifaximin; RCIFAX, Rifagut; Xifaxan; Zaxine) is an orally bioavailable and semi-synthetic RNA synthesis inhibitor used to treat travelers diarrhea caused by certain bacteria.

Rifaximin Chemical Structure CAS No.: 80621-81-4
Product category: DNA(RNA) Synthesis

This product is for research use only, not for human use. We do not sell to patients.

Size	Price	Stock	Qty
500mg
1g
2g
5g
10g
Other Sizes

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Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Rifaximin (BRN-3584528; L-105SV; Fatroximin; Normix; Rifacol; Rifaxidin; Rifaxin; Ritacol; Rifaximin; RCIFAX, Rifagut, Xifaxan, Zaxine) is an orally bioavailable and semi-synthetic RNA synthesis inhibitor used to treat traveler's diarrhea caused by certain bacteria. It functions by attaching itself to the β subunit of the RNA polymerase that is dependent on bacterial DNA.

Biological Activity I Assay Protocols (From Reference)

Targets

RNA polymerase

ln Vitro

Rifaximin (50 μM) reduces the changes in normal intestinal epithelial cells' production of proinflammatory factors like TNF-α, IL-8, Rantes, and PGE2 brought on by LPS stimulation in IEC. Rifaximin suppresses the NF-κB DNA-binding activity, thereby inhibiting the expression of cytokines and chemokines induced by LPS. Rifaximin (100 μM) effectively decreases the expression of TNFα, IL-8, MIP-3α and Rantes induced by LPS stimulation (100 μg/mL).[1] Rifaximin binds the β subunit of the bacterial DNA-dependent RNA polymerase, inhibiting the initiation of chain formation in RNA synthesis. Rifaximin has a lower MIC against gram-positive bacteria, with an MIC90 at dosages ranging from 0.01 µg/mL to 0.5 µg/mL. Rifaximin has broad-spectrum activity against aerobic and anaerobic gram-positive and gram-negative microorganisms.[2]

ln Vivo

Rifaximin is significantly more concentrated in the gastrointestinal tract than rifampicin. In the gut of hPXR mice, rifaximin treatment significantly increases the expression of PXR target genes, whereas this is not the case in wild-type or Pxr-null mice. The human PXR was activated by rifaximin, but not the other xenobiotic nuclear receptors, such as the farnesoid X receptor, androstane receptor, PPARgamma, and alpha and beta.[3] Due to the activation of genes involved in lipid uptake, rifaximin may cause PXR-dependent hepatocellular fatty degeneration. This suggests that rifaximin may have a deleterious effect on liver function after prolonged exposure.[4]

Cell Assay

Cell Line: Caco-2 cells Concentration: 0.1, 1.0 and 10.0 μM Incubation Time: 48 hours Result: Caused a significant and concentration-dependent reduction in cell proliferation. Reduced the expression of PCNA in a concentration-dependent manner.

Animal Protocol

Balb/c mice (6–8 weeks old) bearing 2,4,6-trinitrobenzene sulfonic acid (TNBS)-induced colitis
10, 30 and 50 mg/kg/day
Orally, p.o. daily for 7 days

References

[1]. Eur J Pharmacol . 2011 Oct 1;668(1-2):317-24.

[2]. Clin Infect Dis . 2006 Feb 15;42(4):541-7.

[3]. J Pharmacol Exp Ther . 2007 Jul;322(1):391-8.

[4]. Toxicol Sci . 2012 Oct;129(2):456-68.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C43H51N3O11

Molecular Weight

785.88

Exact Mass

785.35

Elemental Analysis

C, 65.72; H, 6.54; N, 5.35; O, 22.39

CAS #

80621-81-4

Related CAS #

80621-81-4

Appearance

Solid powder

SMILES

C[C@H]1/C=C/C=C(\C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)/C

InChi Key

NZCRJKRKKOLAOJ-XRCRFVBUSA-N

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

Chemical Name

[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate

Synonyms

BRN-3584528; L-105; BRN 3584528; L105; BRN3584528; L 105SV; Fatroximin; Normix; Rifacol; Rifamycin L 105; Rifaxidin; Rifaximin; Rifaxin; Ritacol; Rifaximin; trade names: RCIFAX, Rifagut; Xifaxan; Zaxine

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: ~47 mg/mL (~59.8 mM)

Water: <1 mg/mL

Ethanol: ~3 mg/mL (~3.8 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 3 mg/mL (3.82 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 3 mg/mL (3.82 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 3: 2.08 mg/mL (2.65 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.2725 mL	6.3623 mL	12.7246 mL
	5 mM	0.2545 mL	1.2725 mL	2.5449 mL
	10 mM	0.1272 mL	0.6362 mL	1.2725 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT04249622	Active Recruiting	Drug: Rifaximin Other: Best Practice	HER2 Positive Breast Carcinoma Anatomic Stage IIIC Breast Cancer AJCC v8	Mayo Clinic	September 18, 2020	Phase 2
NCT03820817	Recruiting	Drug: Rifaximin	Monoclonal Gammopathy Gammopathy Igg	Emory University	May 15, 2019	Phase 1
NCT05587036	Recruiting	Drug: Rifaximin Dietary Supplement: Placebo	Healthy Volunteers Stress	Universitaire Ziekenhuizen KU Leuven	February 2, 2023	Phase 2 Phase 3
NCT04043897	Recruiting	Drug: Rifaximin 550mg	Microscopic Colitis	Eugene F Yen, MD	June 29, 2018	Phase 2
NCT05677282	Recruiting	Drug: Rifaximin 550 MG Drug: Azithromycin 500 MG	Diarrhoea; Acute Diarrhea Travelers	Henry M. Jackson Foundation for the Advancement of Military Medicine	October 28, 2022	Phase 4

Biological Data

HE staining revealed time-dependent administration of rifaximin to hPXR mice demonstrated gradual enhancement of hepatocellular fatty degeneration without nodular hyperplasia. Toxicol Sci . 2012 Oct;129(2):456-68.

Liver triglycerides demonstrated a marked increase in liver from HPXR mice treated with rifaximin for 3 and 6 months (below left). Toxicol Sci . 2012 Oct;129(2):456-68.
Controlled clinical trials of rifaximin in the treatment of traveler's diarrhea. Clin Infect Dis . 2006 Feb 15;42(4):541-7.