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光辉霉素 | 18378-89-7

中文名称
光辉霉素
中文别名
光神霉素;普卡酶素;普卡霉素;金霉酸
英文名称
mithramycin
英文别名
mithramycin A;plicamycin;aureolic acid;(2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one
光辉霉素化学式
CAS
18378-89-7
化学式
C52H76O24
mdl
——
分子量
1085.16
InChiKey
CFCUWKMKBJTWLW-BKHRDMLASA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    180-183 °C
  • 比旋光度:
    D20 -51° (c = 0.4 in ethanol)
  • 沸点:
    761.72°C (rough estimate)
  • 密度:
    1.1576 (rough estimate)
  • 溶解度:
    可溶于DMSO(高达20mg/ml)或乙醇(高达10mg/ml)
  • 物理描述:
    Solid
  • 颜色/状态:
    YELLOW, CRYSTALLINE POWDER SHOWING BIREFRINGENCE
  • 气味:
    ODORLESS
  • 稳定性/保质期:

    HYGROSCOPIC, DECOMP SLOWLY IN LIGHT, & DECOMP IN HEAT

  • 旋光度:
    Specific optical rotation at 20 °C for D (sodium) line = -51 deg (c = 0.4 in ethanol)
  • 解离常数:
    pKa1 = 6.9; pKa2 = 7.7 (naphthalene hydroxyls) (est)

计算性质

  • 辛醇/水分配系数(LogP):
    0.6
  • 重原子数:
    76
  • 可旋转键数:
    15
  • 环数:
    8.0
  • sp3杂化的碳原子比例:
    0.77
  • 拓扑面积:
    358
  • 氢给体数:
    11
  • 氢受体数:
    24

ADMET

毒理性
  • 肝毒性
使用plicamycin进行化疗会导致几乎所有治疗超过1到2天并在治疗期间接受监测的患者出现血清酶平升高。血清ALT、AST和LDH值在首次输注后的3天内开始上升,并在7到10天内达到峰值,平为正常上限(ULN)的5到500倍。然而,这些升高是暂时的,在1到3周内会解决,并且很少伴有症状或黄疸。在这些发作期间进行的肝脏活检通常显示中央小叶坏死和充血。随着治疗的重复进行,升高的情况通常以相同或更低的程度继续发生。曾有一例报告,一名患者因非恶性高血症接受全程剂量的plicamycin治疗4天后,出现了急性肝衰竭,这提示可能是缺血性肝炎或窦状阻塞综合征。除此之外,尽管血清酶升高程度从中等到严重,但它们是暂时的并且是无害的。
Chemotherapy with plicamycin causes serum enzyme elevations in almost all patients who are treated for more than 1 or 2 days and who are monitored during therapy. Serum ALT, AST and LDH values begin to rise within 3 days of the first infusion and peak within 7 to 10 days at levels of 5 to 500 times the upper limit of the normal range (ULN). The elevations, however, are transient and resolve within 1 to 3 weeks and are rarely associated with symptoms or jaundice. Liver biopsies taken during these episodes usually demonstrate centrolobular necrosis and congestion. With repeated courses, elevations continue to occur generally to the same or lesser degree. A single instance of acute liver failure arising within days of therapy that was suggestive of ischemic hepatitis or sinusoidal obstruction syndrome has been reported in a patient treated with full doses of plicamycin for 4 days for nonmalignant hypercalcemia. Otherwise, the serum enzyme elevations, despite being moderate to severe, are transient and benign.
来源:LiverTox
毒理性
  • 相互作用
普卡霉素引起的低凝血酶原血症可能会增加香豆素类和茚满二酮衍生物抗凝剂的活动性,并可能增加接受肝素或溶栓药物治疗的患者的出血风险;不推荐同时使用。
Plicamycin-induced hypoprothrombinemia may increase the activity of coumarin- and indandione-derivative anticoagulants and may increase the risk of bleeding in patient receiving heparin or thrombolytic agents; concurrent use is not recommended.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
同时使用非甾体抗炎药、阿司匹林右旋糖酐双嘧达莫磺吡酮丙戊酸普卡霉素可能会增加出血风险,因为这些药物单独或与普卡霉素联合使用时,可能会通过增加或协同作用降低血液凝固能力,即抑制血小板聚集,同时普卡霉素和大剂量阿司匹林可能会诱导低凝血酶原血症;此外,阿司匹林、非甾体抗炎药或磺吡酮的胃肠道溃疡性或出血潜力可能会增加接受普卡霉素治疗患者的出血风险。
Concurrent use /of nonsteroidal anti-inflammatory drugs, aspirin, dextran, dipyridamole, sulfinpyrazone, or valproic acid/ with plicamycin may increase the risk of hemorrhage because of additive or multiple actions, which may decrease the blood-clotting ability, ie, inhibition of platelet aggregation, by these medications and/or plicamycin combined with induction of hypoprothrombinemia by plicamycin and large dose of aspirin; in ad