11003-38-6

• 常用中文名：卷曲霉素
• 常用英文名：capreomycin
• CAS号：11003-38-6
• 分子式：C₂₅H₄₆N₁₄O₁₂S
• 分子量：766.784
• 相关类别： 原料药 抗生素类药物 多肽类药
• 发布时间：2018-06-16 13:54:36
• 更新时间：2024-01-02 18:12:30
• 卷曲霉素是一种大环肽抗生素。卷曲霉素可用于抗多药耐药结核病的研究。卷曲霉素能抑制分枝杆菌核糖体翻译中苯丙氨酸的合成[1][2]

名称

• 中文名: 卷曲霉素
• 英文名: 3,6-Diamino-N-{[(8Z)-15-amino-11-(2-amino-3,4,5,6-tetrahydro-4-pyrimidinyl)-8-[(carbamoylamino)methylene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide sulfate (1:1)
• 英文别名: 3,6-diamino-N-(((8E)-15-amino-3,6,9,12,16-pentahydroxy-8-(((hydroxy(imino)methyl)amino)methylene)-2-(hydroxymethyl)-11-(2-iminohexahydropyrimidin-4-yl)-1,4,7,10,13-pentaazacyclohexadeca-3,6,9,12,16-pentaen-5-yl)methyl)hexanimidic acid compound with sulfuric acid (1:1); 3,6-Diamino-N-{[(8Z)-15-amino-11-(2-amino-3,4,5,6-tetrahydro-4-pyrimidinyl)-8-[(carbamoylamino)methylene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide sulfate (1:1); Hexanamide, 3,6-diamino-N-[[(8Z)-15-amino-8-[[(aminocarbonyl)amino]methylene]-11-(2-amino-3,4,5,6-tetrahydro-4-pyrimidinyl)-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadec-5-yl]methyl]-, sulfate (1:1) (salt)

物化性质

• 沸点: 1376.7ºC at 760 mmHg
• 分子式: C₂₅H₄₆N₁₄O₁₂S
• 分子量: 766.784
• 闪点: 786.4ºC
• 精确质量: 766.314026
• PSA: 480.83000
• 蒸汽压: 0mmHg at 25°C

生物活性

• 描述: 卷曲霉素是一种大环肽抗生素。卷曲霉素可用于抗多药耐药结核病的研究。卷曲霉素能抑制分枝杆菌核糖体翻译中苯丙氨酸的合成[1][2]
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Mycobacterial[1]

• 体内研究: 卷曲霉素(吸入1.4、7.2和14.5 mg/kg；静脉注射20 mg/kg；4周)降低了受感染豚鼠的湿肺重量,并降低了肺部的细菌负荷[2]。动物模型：雄性豚鼠[836±162.3 g；经呼吸道感染结核分枝杆菌(H37Rv株)2×105 CFU/mL雾化悬浮液][2]剂量：1.4、7.2和14.5 mg/kg吸入；20 mg/kg,静脉注射：吸入或静脉注射。；4周结果：湿肺重量在14.5mg/kg时显著降低,低于1.4mg/kg组和对照组。与对照组(4.58±0.20 CFU/mL)和1.4和7.2 mg/kg(分别为4.02±0.32和4.01±0.29 CFU/mL)相比,14.5 mg/kg组的肺部细菌负荷显著降低(3.52±0.20 CFU/mL；P<0.05)。
• 参考文献:

  [1]. Maus CE, et al. Mutation of tlyA confers capreomycin resistance in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2005 Feb;49(2):571-7.

  [2]. Garcia-Contreras L, et al. Inhaled large porous particles of capreomycin for treatment of tuberculosis in a guinea pig model. Antimicrob Agents Chemother. 2007 Aug;51(8):2830-6.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : EX8920000 CHEMICAL NAME : Capreomycin CAS REGISTRY NUMBER : 11003-38-6 LAST UPDATED : 198910 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 1371 mg/kg/96D-I TOXIC EFFECTS : Vascular - BP elevation not characterized in autonomic section Nutritional and Gross Metabolic - changes in potassium Nutritional and Gross Metabolic - metabolic alkalosis REFERENCE : AJKDDP American Journal of Kidney Diseases. (Grune & Stratton, Inc., Journal Subscription Dept., POB 6280, Duluth, MN 55806) V.1- 1981- Volume(issue)/page/year: 7,245,1986 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 514 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 25,353,1974 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 238 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 25,353,1974

制备

该品产生菌是卷曲链霉菌，发酵操作得到发酵液，采弱酸性丙烯酸系阳离子交换树脂进行提纯、浓缩，再经强酸性苯乙烯系阳离子交换树脂脱盐，弱酸性丙烯酸系阳离子交换树脂脱色，薄膜浓缩。浓缩液经脱色、除热源、无菌过滤、喷雾干燥即得成品。