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Merck

R8626

Sigma-Aldrich

Rifamycin SV sodium salt

potency: ≥ 900 IU/mg (anhydrous basis)

Sinónimos:

2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl- 21-acetate monosodium salt, Rifamycin SV monosodium salt

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About This Item

Fórmula empírica (notación de Hill):
C37H46NNaO12
Número de CAS:
Peso molecular:
719.75
EC Number:
UNSPSC Code:
51283601
PubChem Substance ID:
NACRES:
NA.76

form

powder

Quality Level

potency

≥ 900 IU/mg (anhydrous basis)

solubility

ethanol: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

mode of action

protein synthesis | interferes

SMILES string

[Na+].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)cc([O-])c4c3C2=O

InChI

1S/C37H47NO12.Na/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;/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46);/q;+1/p-1/b11-10+,14-13+,17-12-;/t16-,18+,19+,20+,25-,29-,30+,33+,37-;/m0./s1

InChI key

YVOFSHPIJOYKSH-NLYBMVFSSA-M

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General description

Chemical structure: macrolide

Application

Rifamycin SV is a broad-spectrum semisynthetic antimicrobial agent of the rifamycin group. It is used to study potential genes, such as rif15 and rif16, which may be involved in the conversion of rifamycin SV into rifamycin B.

Biochem/physiol Actions

Rifamycin SV inhibits selective (E. coli, B. subtilis) bacterial DNA-dependent RNA polymerase by binding to the polymerase β-subunit, a mechanism similar to rifabutin. It acts as a selective cytochrome P450 3A4 inducer. It is active against Gram-positive bacteria and is moderately active against Gram-negative organisms.

Packaging

1g,5g

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Light sensitive. Air sensitive. Store under inert gas

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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I Caruso et al.
Annals of the rheumatic diseases, 41(3), 232-236 (1982-06-01)
Thirty rheumatoid patients with persistent knee effusion were treated intra-articularly with rifamycin SV, 500 mg weekly, or with saline solution, 10 ml, in a double-blind study. A complete disappearance of effusion and an impressive clinical improvement was observed in the
Y Kono et al.
Journal of biochemistry, 91(1), 397-401 (1982-01-01)
The formation of Mn2+- or Cu2+-rifamycin SV complex and the semiquinone radical of rifamycin SV was studied by electron spin resonance spectroscopy. The results indicate that: (1) the complexes Mn2+-rifamycin SV (g parallel = 2.265, g perpendicular = 2.087, A
David J Farrell et al.
Antimicrobial agents and chemotherapy, 55(3), 992-996 (2010-12-15)
Rifamycin SV is a broad-spectrum, poorly absorbed antimicrobial agent that, when coupled with MMX technology, is being targeted for the oral treatment of traveler's diarrhea (TD) and Clostridium difficile-associated disease (CDAD). Rifamycin SV was tested for activity against 911 TD-associated
Dimova Velichka et al.
Recent patents on anti-infective drug discovery, 5(1), 76-90 (2009-11-26)
A new rifamycin derivative 3-(4-cinnamyl-piperazinyl iminomethyl) rifamycin SV (T9) and its sodium salt (T11, Rifacinna((R))) were in vitro, in vivo, toxicologically and clinically investigated in comparison with rifampicin, rifapentine, rifabutin, rifalazil. Our experiments showed that Rifacinna exhibits excellent in vitro
P Sharma et al.
Xenobiotica; the fate of foreign compounds in biological systems, 40(1), 24-37 (2009-11-19)
Transporters are carrier proteins that may influence pharmacokinetic, pharmacodynamic, and toxicological characteristics of drugs. The development of validated in vitro transporter models is imperative to support regulatory submissions of drug candidates. This study is focused on utilizing human embryonic kidney

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