13553-79-2

• 常用中文名：利福霉素S
• 常用英文名：RifamycinS
• CAS号：13553-79-2
• 分子式：C₃₇H₄₅NO₁₂
• 分子量：695.753
• 相关类别： 原料药 抗生素类药物 利福霉素类药
• 发布时间：2018-03-20 08:00:00
• 更新时间：2024-01-02 08:52:31
• 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。

名称

• 中文名: 利福霉素-S
• 英文名: Rifamycin S
• 中文别名: 利福霉素 S; 利福霉素S; 利福霉素; 利福平霉素
• 英文别名: Rifamycin,1,4-dideoxy-1,4-dihydro-1,4-dioxo; UNII-PI53N820JV; rifomycin-S; rifamycin-S; (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-Trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1.0]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate; NCI 144-130; (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate; EINECS 236-938-4; 2,7-(Epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone, 21-(acetyloxy)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-; (12S,3E,5S,13E,15Z)-7t-acetoxy-15,9c,11t-trihydroxy-5r-methoxy-12,4,6t,8c,10c,12t,16-heptamethyl-2-oxa-18-aza-1(2,7)-naphtho[2,1-b]furana-cyclooctadecaphane-3,13,15-triene-11,6,9,17-tetraone; rifaximin S; O1,O4-didehydro-rifamycin; (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-Trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1.0]triaconta-1(28),2,4,9 ,19,21,25-heptaen-13-yl acetate; 1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin; RifamycinS

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 917.4±65.0 °C at 760 mmHg
• 熔点: 179-181ºC (dec.)
• 分子式: C₃₇H₄₅NO₁₂
• 分子量: 695.753
• 闪点: 508.6±34.3 °C
• 精确质量: 695.294189
• PSA: 194.99000
• LogP: 2.87
• 外观性状: 黄色橙色结晶粉末
• 蒸汽压: 0.0±0.3 mmHg at 25°C
• 折射率: 1.605
• 储存条件: 2-8°C
• 计算化学:

  1.疏水参数计算参考值（XlogP）:4.1

  2.氢键供体数量:4

  3.氢键受体数量:12

  4.可旋转化学键数量:3

  5.互变异构体数量:339

  6.拓扑分子极性表面积:195

  7.重原子数量:50

  8.表面电荷:0

  9.复杂度:1480

  10.同位素原子数量:0

  11.确定原子立构中心数量:9

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:3

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: 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。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Gram-positive bacteria[3] Reactive oxygen species (ROS)[1]

• 体外研究: 利福霉素SV对细菌生长的抑制作用是由于细胞内的氧化还原循环产生活性氧。金属离子Mn2+、Cu2+、Co2+诱导利福霉素SV氧化为利福霉素S。最有效的金属离子是Mn2+[2]。
• 体内研究: 大鼠肝线粒体亚颗粒在NADH和利福霉素存在下也产生羟基自由基。NADH脱氢酶(复合物I)是参与利福霉素S还原的主要成分。与NADPH相比,NADH在催化这些抗生素与大鼠肝微粒体相互作用方面几乎同样有效(利福霉素S)。利福霉素S很容易被铁(II)还原成相应的对苯二酚利福霉素SV。利福霉素S形成可检测的Fe(II)-(利福霉素S)3复合物。Fe:ATP诱导的脂质过氧化被利福霉素S完全抑制。利福霉素S可与大鼠肝微粒体相互作用,进行氧化还原循环,当存在铁络合物时,随后产生羟基自由基[1]。
• 参考文献:

  [1]. Rao DN, et al. A comparative study of the redox-cycling of a quinone (rifamycin S) and a quinonimine (rifabutin) antibiotic by rat liver microsomes. Free Radic Biol Med. 1997;22(3):439-46.

  [2]. Kono Y. Oxygen Enhancement of bactericidal activity of rifamycin SV on Escherichia coli and aerobic oxidation of rifamycin SV to rifamycin S catalyzed by manganous ions: the role of superoxide. J Biochem. 1982 Jan;91(1):381-95.

  [3]. Huang H, et al. Rifamycin S and its geometric isomer produced by a newly found actinomycete, Micromonospora rifamycinica. Antonie Van Leeuwenhoek. 2009 Feb;95(2):143-8.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : KD1925000 CHEMICAL NAME : 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b) furan-1,6,9,11(2H)-te trone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22 -heptamethyl-, 21-acetate CAS REGISTRY NUMBER : 13553-79-2 LAST UPDATED : 199612 DATA ITEMS CITED : 3 MOLECULAR FORMULA : C37-H45-N-O12 MOLECULAR WEIGHT : 695.83 WISWESSER LINE NOTATION : T C6 B65-24- A D E 2BC G& AV DV GV LO NO F&VM OU B&U D&U MHT&&TJ IQ J1 M1 QO1 R1 SOV1 T1 UQ V HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >3 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 16,412,1960 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 258 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,865,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 122 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,865,1978

安全

• RTECS号: KD1925000
• 海关编码: 2941903000

合成路线

13929-35-6 ~92% 13553-79-2

文献：Seong, Baik Lin; Han, Moon Hi Chemistry Letters, 1982 , p. 627 - 628

14487-05-9 ~% 13553-79-2

文献：Journal of the Chemical Society, Chemical Communications, , p. 395 - 396

54356-09-1 ~% 13553-79-2

文献：Journal of the Chemical Society, Chemical Communications, , p. 395 - 396

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