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R3501 Sigma-Aldrich

Rifampicin

≥97% (HPLC), powder

Synonym: 3-(4-Methylpiperazinyliminomethyl)rifamycin SV, Rifampin, Rifamycin AMP

  • CAS Number 13292-46-1

  • Empirical Formula (Hill Notation) C43H58N4O12

  • Molecular Weight 822.94

  •  Beilstein Registry Number 5723476

  •  EC Number 236-312-0

  •  MDL number MFCD00151389

  •  PubChem Substance ID 57654590

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Application,
InChI Key   JQXXHWHPUNPDRT-WLSIYKJHSA-N
assay   ≥97% (HPLC)
form   powder
color   faintly orange to red-brown
pKa    1.7 (4-hydroxyl group)
pI    4.84
pKa    7.9 (4-piperazine nitrogen)
solubility   H2O: 1.3 mg/mL (pH 4.3)
  DMSO: 100 mg/mL
  H2O: 2.5 mg/mL at 25 °C (pH 7.3)
  chloroform: soluble 50 mg/mL
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
  mycobacteria
  viruses
storage temp.   −20°C

Description

Biochem/physiol Actions

Inhibits the assembly of DNA and protein into mature virus particles.

Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.

Rifampicin inhibits the assembly of DNA and protein into mature virus particles. It inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase, which results in cell death.

Packaging

1, 5, 25 g in glass bottle

250 mg in glass insert

Application

Rifampicin is used to treat Tuberculosis and Tuberculosis-related mycobacterial infections. It is widely used as an antipruritic agent in the autoimmune cholestatic liver disease, primary biliary cirrhosis (PBC). It has been shown to cause hepatitis.

General description

Chemical structure: macrolide

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Product is sensitive to light and moisture.Store under inert gas. Keep in a dry place

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
VJ7000000

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
How is the potency determined for Product R3501, Rifampicin?
The potency is determined from a microbiological assay (USP XXII) for antibiotics, a 2-level assay. The test organism is Bacillus subtilis ATCC 6633. The minimum dose is 4.0 μg/ml and the maximum dose is 8.0 μg/ml.
The label advises that I should store Product R3501, Rifampicin, frozen. But when it arrived there was no ice in the package. Why is that?
This product in its powder form is stable for short periods of time (i.e., the shipping process), at ambient temperature.For long term storage it is best to store it at -20°C.
What is the difference between the various Rifampicin products available from Sigma-Aldrich?
Sigma-Aldrich offers several Rifampicin products, each tested and best suited for specific applications.The products range from a general use research grade to sterile powder, to plant culture tested.See individual products for specific details.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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Protocols & Articles

Articles

Inhibition of Nucleic Acid Synthesis by Antibiotics

Quinolones are a key group of antibiotics that interfere with DNA synthesis by inhibiting topoisomerase, most frequently topoisomerase II (DNA gyrase), an enzyme involved in DNA replication. DNA gyra...
BioFiles 2006, 1.4, 7.
Keywords: Antibiotics, Antitumor agents, Cancer, DNA replication

Rapid Analysis of Rifampicin Using Discovery LC-MS Stationary Phases

The desire for quality data in an increasingly timely manner places a significant burden on the modern analytical laboratory. In this article, the use of short LC-MS columns are shown to provide fast...
David Bell
Reporter EU Volume 13
Keywords: Antibiotics, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Reductions, Separation

Related Content

Antibiotics Selection Guide

The Antibiotic Selection Guide enables researchers to spend more time on their research discoveries and less time seeking established antibiotic information. Link to hundreds of antibiotics for conta...
Keywords: Antibiotics, Cell biology, Cell culture, Genetic, High performance liquid chromatography, Reversed-phase chromatography

Peer-Reviewed Papers
15

References

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