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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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Product Name

Rifamycin SV sodium salt, potency: ≥ 900 IU/mg (anhydrous basis)

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

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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.

General description

Chemical structure: macrolide

Other Notes

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

Packaging

1g,5g

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
0000440227
0000440227
0000440226
0000440226
WXBF5088V

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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
Clinical efficacy of rifamycin SV combined with oxytetracycline in the treatment of caseous lymphadenitis in sheep.
S Senturk et al.
The Veterinary record, 159(7), 216-217 (2006-08-15)
Zhihui Shao et al.
Archives of microbiology, 193(7), 463-477 (2011-03-23)
Nitrate assimilation has been well studied for Gram-negative bacteria but not so much in the Gram-positive actinomycetes up to date. In a rifamycin SV-producing actinomycete, Amycolatopsis mediterranei strain U32, nitrate not only can be used as a sole nitrogen source
Wei Zhao et al.
Cell research, 20(10), 1096-1108 (2010-06-23)
Amycolatopsis mediterranei is used for industry-scale production of rifamycin, which plays a vital role in antimycobacterial therapy. As the first sequenced genome of the genus Amycolatopsis, the chromosome of strain U32 comprising 10,236,715 base pairs, is one of the largest
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