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R3501

Rifampicin

Name: Rifampicin
Brand: SIGMA

≥95% (HPLC), powder or crystals

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₄₃H₅₈N₄O₁₂

CAS Number:

13292-46-1

Molecular Weight:

822.94

UNSPSC Code:

51283601

NACRES:

NA.76

PubChem Substance ID:

57654590

EC Number:

236-312-0

Beilstein/REAXYS Number:

5723476

MDL number:

MFCD00151389

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Properties

Quality Level

200

assay

≥95% (HPLC)

form

powder or crystals

color

Reddish-brown

pI

4.84

pKa

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

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

Description

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

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.

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

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pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

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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Certificates of Analysis (COA)

Lot/Batch Number

0000547473

0000547482