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Merck

R3501

Rifampicin

≥95% (HPLC), powder or crystals

Synonym(s):

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

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250 MG

€52.90

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€151.00

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€439.45

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€1,776.50

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About This Item

Empirical Formula (Hill Notation):
C43H58N4O12
CAS Number:
Molecular Weight:
822.94
UNSPSC Code:
51283601
NACRES:
NA.76
PubChem Substance ID:
EC Number:
236-312-0
Beilstein/REAXYS Number:
5723476
MDL number:

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Product Name

Rifampicin, ≥95% (HPLC), powder or crystals

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

InChI key

JQXXHWHPUNPDRT-WLSIYKJHSA-N

SMILES string

CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)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]1C)c(\C=N\N5CCN(C)CC5)c(O)c4c3C2=O

assay

≥95% (HPLC)

form

powder or crystals

color

Reddish-brown

pKa 

1.7 (4-hydroxyl group)
7.9 (4-piperazine nitrogen)

pI 

4.84

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria
viruses

mode of action

protein synthesis | interferes

storage temp.

−20°C

Quality Level

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This Item
R07000005573031604009
mode of action

protein synthesis | interferes

mode of action

-

mode of action

-

mode of action

-

antibiotic activity spectrum

Gram-negative bacteria, mycobacteria, Gram-positive bacteria, viruses

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

-

assay

≥95% (HPLC)

assay

-

assay

~97-102% (by Assay)

assay

-

form

powder or crystals

form

-

form

powder (or crystals)

form

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

Application

Rifampicin is used to treat Tuberculosis and Tuberculosis-related mycobacterial infections[1]. 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[2].

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[1].

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

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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M I Prince et al.
Gut, 50(3), 436-439 (2002-02-13)
There is evidence to suggest that rifampicin is an effective second line therapy for controlling pruritus in patients with chronic cholestatic liver disease. It is most widely used as an antipruritic agent in the autoimmune cholestatic liver disease, primary biliary
Sandra V Kik et al.
The Journal of infectious diseases, 211 Suppl 2, S58-S66 (2015-03-15)
The potential available market (PAM) for new diagnostics for tuberculosis that meet the specifications of the high-priority target product profiles (TPPs) is currently unknown. We estimated the PAM in 2020 in 4 high-burden countries (South Africa, Brazil, China, and India)
Rodney Dawson et al.
Lancet (London, England), 385(9979), 1738-1747 (2015-03-22)
New antituberculosis regimens are urgently needed to shorten tuberculosis treatment. Following on from favourable assessment in a 2 week study, we investigated a novel regimen for efficacy and safety in drug-susceptible and multidrug-resistant (MDR) tuberculosis during the first 8 weeks
Daniela Baldoni et al.
Antimicrobial agents and chemotherapy, 53(3), 1142-1148 (2008-12-17)
We investigated the activity of linezolid, alone and in combination with rifampin (rifampicin), against a methicillin-resistant Staphylococcus aureus (MRSA) strain in vitro and in a guinea pig model of foreign-body infection. The MIC, minimal bactericidal concentration (MBC) in logarithmic phase
Federica Michielin et al.
Cell reports, 33(9), 108453-108453 (2020-12-03)
The specification of the hepatic identity during human liver development is strictly controlled by extrinsic signals, yet it is still not clear how cells respond to these exogenous signals by activating secretory cascades, which are extremely relevant, especially in 3D

Articles

Discover critical characteristics to consider when working with enzyme inhibitors, such as cell permeability, the prozone effect, and Lipinski’s rule of 5.

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Product Information Sheet

Questions

1–8 of 8 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. What is the stability of Rifampicin (0.1%) in water at room temperature?

    1 answer
    1. The stability of Rifampicin solutions prepared in only water has not been investigated. However, stock solutions prepared in water-ethanol (8:2), at 1 mg/mL, are stable for up to 8 weeks when stored refrigerated or at room temperature. Please see the link below to review additional information available in the product datasheet:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/522/389/r3501pis.pdf

      Helpful?

  3. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  4. What solvent should be used to reconstitute item R3501, Rifampicin?

    1 answer
    1. Rifampicin is soluble in CHCl3. Additionally, it is soluble in water at pH 4.3 (1.3 mg/ml), methanol (25 mg/ml), DMSO (25 mg/ml), dimethyl sulfoxide, tetrahydrofuran, and water at pH 7.3 (2.5 mg/ml at 25°C).

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  5. How is the potency determined for Product R3501, Rifampicin?

    1 answer
    1. 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.

      Helpful?

  6. 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?

    1 answer
    1. 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.

      Helpful?

  7. What is the difference between the various Rifampicin products available from Sigma-Aldrich?

    1 answer
    1. 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.

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  8. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

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