[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
• 化学式: C₃₂H₄₈O₉
• 分子量: 576.7
• InChiKey: JLPDBLFIVFSOCC-UJQZKUKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

ADMET

毒理性

• 毒性总结

鉴定和使用：欧勒安酸是一种固体。它是一种在植物欧勒安德（普通夹竹桃）和秘鲁欧勒安德（黄色夹竹桃）中发现的强心苷。人类暴露和毒性：摄入欧勒安酸会导致恶心、呕吐、腹痛、腹泻、心律失常和高血压。在夹竹桃中毒的情况下，瞳孔散大通常伴随着眩晕、抽搐、昏迷和心动过缓。意外摄入可能导致心脏心律失常甚至死亡。已有多起致命和非致命中毒的报道。动物研究：在夹竹桃生长的地区，马科动物腹痛应该将夹竹桃中毒作为鉴别诊断，特别是当同时检测到氮质血症或心脏心律失常时。生态毒性研究：对于淡水鱼C. punctatus来说，暴露于亚致死剂量的欧勒安酸24小时和96小时，会导致肝脏和肌肉组织中的总蛋白、总游离氨基酸、核酸、糖原、丙酮酸、乳酸以及酶蛋白酶、磷酸酶、丙氨酸转氨酶、天冬氨酸转氨酶和乙酰胆碱酯酶活性显著变化。

IDENTIFICATION AND USE: Oleandrin is a solid. It is a cardiac glycoside found in plants Nerium oleander (common oleander) and Thevetia peruviana (yellow oleander). HUMAN EXPOSURE AND TOXICITY: Ingestion of either oleandrin results in nausea, vomiting, abdominal pain, diarrhea, dysrhythmias, and hyperkalemia. In poisoning by oleander, mydriasis characteristically accompanies vertigo, convulsions, coma, and bradycardia. Accidental ingestion can cause cardiac arrhythmias and even death. Several cases of fatal and non-fatal poisoning have been reported. ANIMAL STUDIES: Oleander intoxication should be a differential diagnosis for equids with colic in geographic areas where oleander is found, especially when azotemia or cardiac arrhythmias are detected concurrently. ECOTOXICITY STUDIES: For freshwater fish C. punctatus exposure to sub-lethal doses of oleandrin for 24 hr and 96 hr caused significant alteration in the level of total protein, total free amino acid, nucleic acid, glycogen, pyruvate, lactate and enzyme protease, phosphatases, alanine aminotransferase, aspartate aminotransferase and acetylcholinesterase activity in liver and muscle tissues.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

Oleandrin 很可能通过抑制 Na+,K+-ATPase 来发挥其毒性作用。

Oleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase. (A2831)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

夹竹桃苷对胃肠道和心脏都有影响。这种植物的毒性反应也可能影响中枢神经系统，可能导致昏迷，最终导致死亡。

Oleandrin causes both gastrointestinal and cardiac effects. Reactions to poisonings from this plant can also affect the central nervous system, possibly resulting in coma that can lead to death. (L1253)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（摄入）（L1817）；皮肤（L1817）

Oral (ingestion) (L1817) ; dermal (L1817)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

(3)Holeandrin 是 Anvirzel 的一个心脏糖苷成分。在小鼠中进行 (3)Holeandrin 的药代动力学研究，分别通过静脉注射（40ug/kg）和口服（80ug/kg）给药。口服给药后，oleandrin 迅速吸收（20分钟达到 Cmax），尽管消除半衰期较长（2.3±0.5小时），但比静脉注射给药（0.4±0.1小时）要长。静脉注射和口服给药后的 AUC0-infinity 值分别为 24.6±11.1 和 14.4±4.3（ng·小时/mL），口服生物利用度约为 30%。静脉给药后，肝脏中 oleandrin 的浓度是心脏或肾脏组织的两倍左右。在这些组织中还发现了 oleandrin 的苷元 oleandrigenin。在 5 分钟时，肝脏中总放射活性的>60% 是由于 oleandrin，而给定剂量的 28% 作为 oleandrigenin 存在。注射后 24 小时，8% 的总放射性通过尿液排出，其中包含 oleandrigenin（占注射剂量的 4.4%）和 oleandrin（1.9%）。66% 的注射放射性活性在粪便中发现，oleandrin 和 oleandrigenin 的含量相等。在大脑中，通过 LC/MS/MS 测量，oleandrin 在注射提取物后的含量高于等效剂量的 oleandrin。数据表明，夹竹桃提取物中的某些成分可能增强 oleandrin 通过血脑屏障的转运。

Pharmacokinetic studies of (3)H oleandrin, a cardiac glycoside component of Anvirzel, were conducted in mice after either an i.v. dose (40 ug/kg) or a p.o. dose (80 ug/kg). Oleandrin was rapidly absorbed after oral dosing (Cmax at 20 min) although the elimination half-life was longer (2.3 +/- 0.5 hr) than that after i.v. dosing (0.4 +/- 0.1 hr). The AUC0-infinity values obtained after i.v. and p.o. dosing were 24.6 +/- 11.1 and 14.4 +/- 4.3 (ng.hr/mL), respectively, resulting in an oral bioavailability of approximately 30%. After i.v. administration, oleandrin concentration in liver was approximately twice that measured in heart or kidney tissue. Oleandrigenin, the aglycone of oleandrin, was also found in these tissues. At 5 min, > 60% of the total radioactivity in liver was due to oleandrin while 28% of the given dose was present as oleandrigenin. Twenty-four hours following injection, 8% of total radioactivity was excreted in urine and contained both oleandrigenin (4.4% of the injected dose) and oleandrin (1.9%). Sixty-six percent of injected radioactivity was found in feces and consisted of oleandrin and oleandrigenin in equal amounts. Uptake of oleandrin in brain after i.p. injection of oleandrin (3 mg/kg) or oleander extract (700 mg/kg) was examined. Measured by LC/MS/MS, oleandrin content in brain was higher following injection of extract than it was with an equivalent dose of oleandrin. The data suggest that components within oleander extract may enhance transport of oleandrin across the blood brain barrier.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

由于对兔进行N夹竹桃的煎剂或浸剂的毒性被认为是由于各种器官中的夹竹桃苷含量造成的。心脏、胃、肾脏和血液含有最高的夹竹桃苷浓度，而肺和大脑则不含。

The toxicity due to an infusion or decoction of N oleander into rabbits was attributed to the oleandrin content in various organs. The heart, stomach, kidneys, and blood contained the greatest oleandrin concentrations, whereas the lung and brain contained none.

来源:Hazardous Substances Data Bank (HSDB)