利福霉素S

中文名称:

利福霉素S

中文同义词:

利福霉素 S;利福霉素;2,7-(环氧十五碳环[1,11,13]三烯亚氨基)萘并[2,1-B]呋喃-1,6,9,11(2H)-四酮,5,17,19,21-四羟基-23- 甲氧基-2,4,12,16,18,20,22-七甲基-,21-乙酸酯;利福霉素钠EP杂质E;利福昔明杂质E (EP/BP);利福霉素-D4;利福平霉素;利福霉素S

英文名称:

Rifamycin S

英文同义词:

1,4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin;2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,6,9,11(2h)-tetron;4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin;RIFAMPICIN S;RIFAMYCIN S;Rifaximin EP Impurity E (Rifamycin S);2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate (7CI,8CI);Rifamycin EP Impurity B

CAS号:

13553-79-2

分子式:

C37H45NO12

分子量:

695.75

EINECS号:

236-938-4

相关类别:

医药原料;对照品-杂质对照品;原料药API;原料;化工中间体工业原料;Antibiotics;Chiral Reagents;Intermediates Fine Chemicals;Pharmaceuticals

Mol文件:

13553-79-2.mol

熔点 

179-181°C (dec.)

比旋光度 

D20 +476° (c = 0.1 in methanol)

沸点 

700.89°C (rough estimate)

密度 

1.2387 (rough estimate)

折射率 

1.6630 (estimate)

形态

neat

酸度系数(pKa)

3.85±0.70(Predicted)

最大波长(λmax)

390nm(MeOH)(lit.)

Merck 

14,8217

InChIKey

BTVYFIMKUHNOBZ-ODRIEIDWSA-N

生物活性

Rifamycin S 是一种醌和抗革兰氏阳性细菌 (包括 MRSA) 的抗生素。Rifamycin S 是涉及两个电子的可逆氧化还原系统的氧化形式。Rifamycin S 可以产生活性氧 (ROS) 并抑制微粒体脂质过氧化，并可用于肺结核和麻风病的研究。

靶点

Gram-positive bacteria Reactive oxygen species (ROS)

体外研究

The inhibition of bacterial growth by Rifamycin SV is due to the production of active species of oxygen resulting from the oxidation-reduction cycle of Rifamycin SV in the cells. The aerobic oxidation of Rifamycin SV to Rifamycin S is induced by metal ions, such as Mn 2+ , Cu 2+ , and Co 2+ . The most effective metal ion is Mn 2+ .

体内研究

Rat liver sub-mitochondrial particles also generated hydroxyl radical in the presence of NADH and Rifamycin S. NADH dehydrogenase (complex I) as the major component involved in the reduction of Rifamycin S. Compared to NADPH, NADH is almost as effective (Rifamycin S) in catalyzing the interactions of these antibiotics with rat liver microsomes. Rifamycin S is shown to be readily reduced to Rifamycin SV, the corresponding hydroquinone by Fe(II). Rifamycin S forms a detectable Fe(II)-(Rifamycin S)3 complex. The Fe:ATP induced lipid peroxidation is completely inhibited by Rifamycin S. Rifamycin S can interact with rat liver microsomes to undergo redox-cycling, with the subsequent production of hydroxyl radicals when iron complexes are present.

用途 

用作医药中间体。

RTECS号

KD1925000

毒性

LD50 in mice (mg/kg): 122 i.v.; 258 i.p.; 3000 orally (Sensi, 1964)