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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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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

Key Documents

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Product Name

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

pI 

4.84

InChI key

JQXXHWHPUNPDRT-WLSIYKJHSA-N

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

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)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria
viruses

mode of action

protein synthesis | interferes

storage temp.

−20°C

Quality Level

200

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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.

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
GHS07

signalword

Warning

hcodes

H302

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
WXBD4775V
WXBD0542V
WXBC9631V
049M4833V
019M4861V

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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
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)
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
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
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