Rifampin (Rifampicin)

Alias: Rimactane; Arficin; Arzide; Rifampicin; Rifadin; Rifampin; Rimactane; Rimactan; Tubocin; Archidyn; Benemicin; Doloresum; Eremfat; Fenampicin; Sinerdol

Cat No.:V1468 Purity: ≥98%

COA Product Data Instructions for use SDS

Rifampin (Rimactane; Arficin; Arzide; Rifampicin; Rifadin; Rimactane; Rimactan; Tubocin; Archidyn; Benemicin; Doloresum; Eremfat; Fenampicin; Sinerdol), an approved broad spectrum and semisynthetic antibiotic found in Streptomyces mediterranei, is mainly used to treat various bacterial infections such as TB-tuberculosis, leprosy,mycobacterium avium complex, and Legionnaires disease.

Rifampin (Rifampicin) Chemical Structure CAS No.: 13292-46-1
Product category: DNA(RNA) Synthesis

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

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

Cell 2020,183:1202-1218.e25.

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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.

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

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

Product Description

Rifampin (Rimactane; Arficin; Arzide; Rifampicin; Rifadin; Rimactane; Rimactan; Tubocin; Archidyn; Benemicin; Doloresum; Eremfat; Fenampicin; Sinerdol), an approved broad spectrum and semisynthetic antibiotic found in Streptomyces mediterranei, is mainly used to treat various bacterial infections such as TB-tuberculosis, leprosy, mycobacterium avium complex, and Legionnaires' disease. It functions as an inhibitor of DNA-dependent RNA polymerase.

Biological Activity I Assay Protocols (From Reference)

Targets

RNA polymerase

ln Vitro

Rifampin prevents the phosphorylation of mitogen-activated protein kinase (MAPK) and the degradation of IκBα. It is discovered that the binding between rifampin and human MD-2 is concentration-dependent. NF-κB activation triggered by LPS (20 ng/ml) is inhibited by rifampin in a dose-dependent manner, with an IC50 of 44.1 μM in immunocompetent microgial BV-2 cell and Blue hTLR4 293 cells (A). The maximum NF-κB level induced by LPS in the presence of Rifampin (50 μM) is significantly lower than that in the absence of Rifampin. Rifampin (50 μM) suppresses NF-κB activation at varying LPS doses. Rifampin, with an IC50 of 21.2 μM, inhibits NO production in BV-2 cells in a dose-dependent manner when LPS (200 ng/ml) is added. In both microglia BV-2 and RAW 264.7 macrophage cells, rifampin inhibits the production of TNF-α and IL-1β induced by LPS. The pregnane X receptor (NR1I2) is not necessary for rifampin-inhibiting innate immune signaling.[1] When rifampin is combined with polyester vascular prostheses (PVP) functionalized with cyclodextrin (PVP-CD), it significantly reduces bacterial adhesion and inhibits Gram-positive bacteria's ability to grow.[2] In stationary-phase cultures, Rifampin (50 μg/mL) significantly lowers the CFU counts, and in log-phase cultures, it completely eliminates the CFU counts. Since rifampin is bactericidal and begins to kill M. tuberculosis within an hour of exposure, it is especially appropriate.[3]

ln Vivo

Rifampicin (200, 400 mg/kg) can cause fatty liver at high concentration. In vivo treatment of S464P biofilms with rifampicin (30 mg/kg, i.p.) causes a slight decrease, but earlier rebinds in bioluminescence from these catheters in comparison to the parental signal; in contrast, rifampicin has no effect on bioluminescence in mice infected with mutant H481Y.

Animal Protocol

In brief, groups of nine mice per strain receive subcutaneous implants of a 1 cm Teflon (14-gauge) catheter containing 104 cfu S. aureus, either the parental strain Xen 29 or the RifR mutants S464P or H481Y. Every animal has one catheter segment inserted on each side. Five mice per group are given rifampicin (30 mg/kg) intraperitoneally in 0.1 mL saline twice a day for four days straight, six days after the catheters are implanted. As controls, each group's final four mice are not given any medication. The IVIS^® manifold is used to continuously flow 1.5% isoflurane to anesthetize the mice at different stages of the infection. An IVIS^® Image System 100 Series is then used to image the mice. During the course of the infection, the bioluminescent signals (photons/s) that the mice emit are plotted and analyzed using LivingImage^® software. Eleven days after the last rifampicin treatment, or twenty days after infection, the mice are killed. To assess the amount of bacteria on the catheters, the catheters are surgically removed, and the bacteria are separated using sonication.

References

[1]. FASEB J . 2013 Jul;27(7):2713-22.

[2]. J Infect . 2014 Feb;68(2):116-24.

[3]. J Bacteriol . 2000 Nov;182(22):6358-65.

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

Physicochemical Properties

Molecular Formula

C43H58N4O12

Molecular Weight

822.94

Exact Mass

822.41

Elemental Analysis

C, 62.76; H, 7.10; N, 6.81; O, 23.33

CAS #

13292-46-1

Related CAS #

13292-46-1(Rifampicin)

Appearance

Solid powder

SMILES

C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(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)C)O)O)/C=N/N5CCN(CC5)C)/C

InChi Key

JQXXHWHPUNPDRT-WLSIYKJHSA-N

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,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1

Chemical Name

[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate

Synonyms

Rimactane; Arficin; Arzide; Rifampicin; Rifadin; Rifampin; Rimactane; Rimactan; Tubocin; Archidyn; Benemicin; Doloresum; Eremfat; Fenampicin; Sinerdol

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: 25~100 mg/mL (30.4~121.5 mM)

Water: <1 mg/mL

Ethanol: <1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (3.04 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 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: ≥ 2.5 mg/mL (3.04 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 25.0 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	1.2152 mL	6.0758 mL	12.1516 mL
	5 mM	0.2430 mL	1.2152 mL	2.4303 mL
	10 mM	0.1215 mL	0.6076 mL	1.2152 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)

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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
NCT04166474	Active Recruiting	Drug: Dolutegravir	Hiv Tuberculosis	Helen Reynolds	November 18, 2021	Phase 4
NCT00750841	Active Recruiting	Drug: cediranib	Solid Tumors	AstraZeneca	September 9, 2008	Phase 1
NCT05057949	Active Recruiting	Drug: Larotinib Drug: Rifampin	Healthy Volunteers	Sunshine Lake Pharma Co., Ltd.	November 24, 2021	Phase 1
NCT04121195	Active Recruiting	Drug: Dose escalation	HIV/AIDS Tuberculosis	University of Liverpool	October 30, 2020	Phase 2 Phase 3
NCT06081361	Not yet recruiting	Drug: Bedaquiline Drug: Delamanid	Rifampicin-resistant Tuberculosis Pulmonary Tuberculosis	Beijing Chest Hospital	November 1, 2023	Phase 3

Biological Data

Effects of different concentrations of rifampin on the viability of log-phase and stationary-phase cultures of M. tuberculosis H37Rv. J Bacteriol . 2000 Nov;182(22):6358-65.
Rifampin binds to MD-2. A) Structure of rifampin. B) Intrinsic fluorescence of MD-2 with the increasing of rifampin concentration. FASEB J . 2013 Jul;27(7):2713-22.
Biophysical characterizations of rifampin binding to human MD-2. A) Different concentrations of rifampin were coated onto the plate as the probe. FASEB J . 2013 Jul;27(7):2713-22.

Rifampin inhibits LPS-induced NF-κB activation in Blue hTLR4 293 cells (A) and immunocompetent microgial BV-2 cell (B, C). A) Blue hTLR4 293 cells, which overexpress human CD14, TLR4, and MD-2, was stimulated with 20 ng/ml LPS, and NF-κB activity was determined by SEAP assay. B) BV-2 NF-κB luciferase reporter cells were treated with 200 ng/ml LPS and varying concentrations of rifampin. FASEB J . 2013 Jul;27(7):2713-22.