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Merck
CN

SBR00087

Rifamycin S

≥96% (HPLC), powder

Synonym(s):

1,4-Dideoxy-1,4-dioxo-rifamycin

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About This Item

Empirical Formula (Hill Notation):
C37H45NO12
CAS Number:
13553-79-2
Molecular Weight:
695.75
UNSPSC Code:
51101500
NACRES:
NA.41

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InChI

1S/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1

InChI key

BTVYFIMKUHNOBZ-ODRIEIDWSA-N

SMILES string

C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=O)C3=C(C2=O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)/C

assay

≥96% (HPLC)

form

powder

color

yellow-orange

antibiotic activity spectrum

Gram-positive bacteria

mode of action

DNA synthesis | inhibits

storage temp.

−20°C

Quality Level

100

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General description

Rifamycin S is a chemical compound that belongs to the class of antibiotics known as rifamycins. It is a natural product produced by the bacterium Amycolatopsis mediterranei and is used primarily as a reference standard for the detection and quantification of rifamycins in various samples. Rifamycin S is chemically related to other rifamycin antibiotics, including rifampicin.

Application

However, it has been used as a precursor in the synthesis of other rifamycin antibiotics, and it has also been used in research studies to investigate the mechanism of action and resistance of rifamycin antibiotics.

Biochem/physiol Actions

Rifamycin S inhibitions bacterial RNA synthesis. Rifamycin S works by binding to a specific subunit of the bacterial RNA polymerase enzyme, which is necessary for the initiation of bacterial RNA synthesis. Binding of Rifamycin S to the RNA polymerase enzyme inhibits its activity, thereby preventing the transcription of bacterial genes into RNA molecules that are essential for bacterial survival. This leads to the inhibition of bacterial growth and ultimately, bacterial death. Rifamycin S has a broad-spectrum activity against different bacterial species.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H373

Hazard Classifications

STOT RE 2 Oral

target_organs

Kidney

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000401613
0000401613

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