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Merck
CN

R8626

Rifamycin SV sodium salt

potency: ≥ 900 IU/mg (anhydrous basis)

Synonym(s):

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

Empirical Formula (Hill Notation):
C37H46NNaO12
CAS Number:
14897-39-3
Molecular Weight:
719.75
PubChem Substance ID:
329824038
UNSPSC Code:
51283601
NACRES:
NA.76
EC Number:
238-965-7

Key Documents

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InChI key

YVOFSHPIJOYKSH-NLYBMVFSSA-M

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

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

form

powder

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

Quality Level

200

Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000528490
0000528492
0000528490
0000528492
0000440227

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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
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
Eric Garver et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(12), 2492-2498 (2008-08-30)
Macrolide antibiotics azithromycin (AZI) and clarithromycin (CLARI) are large molecular weight compounds and are substrates for apically polarized efflux transporters such as P-glycoprotein, which can potentially restrict intestinal absorption. However, despite these undesired physicochemical and biopharmaceutical properties, AZI and CLARI
Hao Yu et al.
Archives of microbiology, 188(1), 89-96 (2007-03-17)
Amycolatopsis, genus of a rare actinomycete, produces many clinically important antibiotics, such as rifamycin and vancomycin. Although GlnR of Amycolatopsis mediterranei is a direct activator of the glnA gene expression, the production of GlnR does not linearly correlate with the
Lucy A Woods et al.
Nature chemical biology, 7(10), 730-739 (2011-08-30)
Although small molecules that modulate amyloid formation in vitro have been identified, significant challenges remain in determining precisely how these species act. Here we describe the identification of rifamycin SV as a potent inhibitor of β(2) microglobulin (β(2)m) fibrillogenesis when
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