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R3501

Sigma-Aldrich

Rifampicin

≥95% (HPLC), powder or crystals

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Synonym(s):
3-(4-Methylpiperazinyliminomethyl)rifamycin SV, Rifampin, Rifamycin AMP
Empirical Formula (Hill Notation):
C43H58N4O12
CAS Number:
Molecular Weight:
822.94
Beilstein:
5723476
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

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

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

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

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1 of 4

This Item
R7382PHR1806557303
Rifampicin ≥95% (HPLC), powder or crystals

Sigma-Aldrich

R3501

Rifampicin

Rifampicin suitable for plant cell culture, BioReagent, ≥95% (HPLC), powder or crystals

Sigma-Aldrich

R7382

Rifampicin

Rifampin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1806

Rifampin

Rifampicin Antibiotic that specifically inhibits DNA-dependent RNA polymerase in bacteria by forming an inactive complex.

Sigma-Aldrich

557303

Rifampicin

form

powder or crystals

form

powder or crystals

form

-

form

powder (or crystals)

color

Reddish-brown

color

-

color

-

color

red-brown

antibiotic activity spectrum

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

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

-

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

-

mode of action

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

General description

Chemical structure: macrolide

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.

Biochem/physiol Actions

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.
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.

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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
Samy Figueiredo et al.
Antimicrobial agents and chemotherapy, 53(6), 2657-2659 (2009-03-25)
Two clonally related Acinetobacter baumannii isolates, A1 and A2, were obtained from the same patient. Isolate A2, selected after an imipenem-containing treatment, showed reduced susceptibility to carbapenems. This resistance pattern was related to insertion of the ISAba1 element upstream of
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
Toril Lindbäck et al.
Veterinary research, 41(1), 8-8 (2009-10-03)
Media-based bacteriological testing will fail to detect non-culturable organisms and the risk of consuming viable but non-culturable (VBNC) Listeria monocytogenes is unknown. We have here studied whether L. monocytogenes obtained from seafoods, processing environment and clinical cases enter the VBNC
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

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