(2R)-2-phenyl-2-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile | 1630795-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-phenyl-2-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
• CAS: 1630795-88-8
• 化学式: C₂₀H₂₇NO₁₁
• 分子量: 457.4
• InChiKey: XUCIJNAGGSZNQT-KDDLJKRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  202
• 氢给体数：
  7
• 氢受体数：
  12

ADMET

代谢

苦杏仁苷是一种由葡萄糖、苯甲醛和氰化物组成的化学物质，后者可以通过β-葡萄糖苷酶或乳化酶的作用释放出来。尽管这些酶在哺乳动物组织中找不到，但人类的肠道微生物群似乎拥有这些或类似的酶，能够导致氰化物的释放，从而引起人类中毒。因此，与静脉注射相比，通过口服途径苦杏仁苷的毒性可能高达40倍。

AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE FROM WHICH THE LATTER CAN BE RELEASED BY THE ACTION OF BETA-GLUCOSIDASE OR EMULSIN. ALTHOUGH THESE ENZYMES ARE NOT FOUND IN MAMMALIAN TISSUES, THE HUMAN INTESTINAL MICROFLORA APPEARS TO POSSESS THESE OR SIMILAR ENZYMES CAPABLE OF EFFECTING CYANIDE RELEASE RESULTING IN HUMAN POISONING. FOR THIS REASON AMYGDALIN MAY BE AS MUCH AS 40 TIMES MORE TOXIC BY THE ORAL ROUTE AS COMPARED WITH IV INJECTION.

来源:Hazardous Substances Data Bank (HSDB)

代谢

植物苷类通过酶促或酸性水解产生氰化物，以及糖和芳香醛。常见的例子是苦杏仁中的苦杏仁苷（龙胆二糖+苯甲醛+氢氰酸）。在植物组织中，与苷类共存的一种酶复合物，乳糖酶，催化苷类的水解，首先转化为mandelonitrile或p-羟基mandelonitrile，然后转化为苯甲醛或p-羟基苯甲醛和氢氰酸。这些醛被氧化成相应的芳香酸，并以肽结合物的形式排出体外。

...PLANT GLYCOSIDES ARE CHARACTERIZED BY PRODN OF CYANIDE, TOGETHER WITH A SUGAR & AROMATIC ALDEHYDE, ON ENZYMIC OR ACID HYDROLYSIS. COMMON EXAMPLES ARE AMYGDALIN (GENTIOBIOSE + BENZALDEHYDE + HCN) WHICH IS PRESENT IN BITTER ALMONDS... AN ENZYME COMPLEX, EMULSIN, IS PRESENT TOGETHER WITH GLYCOSIDES IN PLANT TISSUES & CATALYZES THE HYDROLYSIS OF GLYCOSIDES, FIRST TO MANDELONITRILE OR P-HYDROXYMANDELONITRILE, & THEN TO BENZALDEHYDE OR P-HYDROXYBENZALDEHYDE, & HCN. ... THE ALDEHYDES ARE OXIDIZED TO CORRESPONDING AROMATIC ACIDS & EXCRETED AS PEPTIDE CONJUGATES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

各种李属植物含有...苦杏仁苷，它可以通过酶类乳化酶水解...在完整的植物中不会发生此类反应；只有在植物组织受损或开始腐烂时，才会开始释放氢氰酸。

...VARIOUS PRUNUS SPECIES CONTAIN...AMYGDALIN, WHICH IS HYDROLYZED BY ENZYME EMULSIN... IN INTACT PLANT NO SUCH ACTION TAKES PLACE; IT IS NOT UNTIL PLANT TISSUE IS DAMAGED OR STARTS TO DECAY THAT LIBERATION OF HCN BEGINS.

来源:Hazardous Substances Data Bank (HSDB)

代谢

糖苷的分解在瘤胃中通常比单胃动物的消化道更容易或更快发生。此外，小分子可以在瘤胃被吸收，从而迅速进入循环。来自蔷薇科成员的氰苷糖苷，如苦杏仁苷的分解就是一个例子。

BREAKDOWN /OF GLYCOSIDES/ OFTEN OCCURS MORE READILY OR MORE RAPIDLY IN RUMEN THAN IN DIGESTIVE TRACT OF MONOGASTRIC ANIMALS. ALSO, SMALL MOLECULES CAN BE ABSORBED AT THE RUMEN & THUS ENTER CIRCULATION RAPIDLY. BREAKDOWN OF CYANOGENIC GLYCOSIDES, SUCH AS AMYGDALIN, FROM MEMBERS OF ROSE FAMILY...IS AN EXAMPLE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

两例苦杏仁苷（杏仁苷）毒性报告，一例为48岁患有淋巴瘤的女性，另一例为46岁患有大细胞未分化肺癌的男性。女性患者在接受每周6毫克静脉注射和每日三次500毫克口服给药后，出现了发热、不适、头痛、严重腹部绞痛、弥漫性斑疹样红斑皮疹、淋巴结病和肝脾肿大。男性患者在接受每日500毫克苦杏仁苷口服给药后，出现了双下肢和上肢进行性神经肌肉无力。两例由口服给药引起的毒性在停药后得到解决。

TWO CASES OF LAETRILE (AMYGDALIN) TOXICITY WERE REPORTED IN A 48-YR-OLD WOMAN WITH LYMPHOMA & A 46-YR-OLD MAN WITH A LARGE CELL ANAPLASTIC CARCINOMA OF THE LUNG. THE WOMAN EXHIBITED FEVER, MALAISE, HEADACHE, SEVERE ABDOMINAL CRAMPS, A DIFFUSE MACULAR ERYTHEMATOUS RASH, LYMPHADENOPATHY & HEPATOSPLENOMEGALY FOLLOWING A WEEKLY 6 MG IV INJECTION & 5OO MG 3 TIMES DAILY ORALLY. THE MAN PRESENTED WITH PROGRESSIVE NEUROMUSCULAR WEAKNESS OF BOTH LOWER & UPPER EXTREMITIES FOLLOWING ORAL ADMIN OF 500 MG OF AMYGDALIN DAILY. BOTH CASES OF TOXICITY RESULTING FROM ORAL ADMIN WAS RESOLVED FOLLOWING DISCONTINUATION OF THE DRUG.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

一位57岁患有乳腺癌的女性因摄入致死剂量的苦杏仁苷（杏仁苷）被送医。入院时，她的氰化物水平为29.0微克/分升。患者在接受对症治疗后有所好转，并被转移到另一家医院，三天后出院。十二天后，患者无生命迹象返回急诊科。尸检显示氰化物水平为218微克/分升，并记录死亡原因为氰化物中毒。

A FATAL LAETRILE (AMYGDALIN) INGESTION BY A 57-YR-OLD FEMALE WITH BREAST CARCINOMA WAS PRESENTED. CYANIDE LEVEL ON ADMISSION TO HOSPITAL WAS 29.0 MCG/DL. THE PT IMPROVED WITH SYMPTOMATIC THERAPY & WAS TRANSFERRED TO ANOTHER HOSPITAL FROM WHICH SHE WAS DISCHARGED 3 DAYS LATER. TWELVE DAYS LATER, THE PT WAS RETURNED TO THE EMERGENCY DEPARTMENT WITH NO SIGN OF LIFE. AN AUTOPSY REVEALED A CYANIDE LEVEL OF 218 MCG/DL & DOCUMENTED THE CAUSE OF DEATH AS CYANIDE POISONING.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

一起氰化物中毒的近致命案例被报告，发生在一名48岁的女性身上，此前她接受了9天的苦杏仁苷（杏仁苷）治疗。苦杏仁苷通过静脉、肌肉注射、口服和直肠给药，同时配合“解毒饮食”。入院时血液中的氰化物水平为116微克/分升。

A NEAR FATAL CASE OF CYANIDE POISONING IS REPORTED IN A 48-YR-OLD WOMAN AFTER A 9 DAY COURSE OF LAETRILE (AMYGDALIN). LAETRILE WAS ADMIN IV, IM, ORALLY, & RECTALLY ALONG WITH A "DETOXIFICATION DIET". BLOOD LEVELS OF CYANIDE ON ADMISSION WERE 116 MUG/DL.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

两起儿童食用杏核后发生的氰化物中毒事件。第一起事件涉及8名儿童，在大量摄入后2小时表现出典型的氰化物中毒迹象和症状；其中7名儿童康复，1名儿童死亡。第二起事件涉及16名食用了由杏核制成的糖果的儿童。症状和体征与第一组相同，但在摄入后半小时出现，并且非常严重。其中三名儿童死亡。

TWO EPISODES OF CYANIDE POISONING OCCURRED IN CHILDREN AFTER INGESTION OF APRICOT KERNELS. THE 1ST EPISODE INVOLVED 8 CHILDREN WHO EXHIBITED TYPICAL SIGNS & SYMPTOMS OF CYANIDE POISONING 2 HR AFTER INGESTION OF LARGE AMOUNTS; 7 CHILDREN RECOVERED & 1 DIED. THE 2ND EPISODE INVOLVED 16 CHILDREN WHO HAD EATEN SWEETS PREPARED FROM KERNELS. SYMPTOMS & SIGNS WERE THE SAME AS THOSE IN THE 1ST GROUP BUT APPEARED 1/2 HR AFTER INGESTION & WERE VERY SEVERE. THREE OF THE CHILDREN DIED.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

杏仁苷是由葡萄糖、苯甲醛和氰化物组成的化学复合物，后者可以释放出来...杏仁苷是苦杏仁苷的主要成分，这种据称具有抗癌作用的药物也曾导致人类氰化物中毒。

AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE FROM WHICH THE LATTER CAN BE RELEASED... AMYGDALIN IS THE MAJOR INGREDIENT OF LAETRILE, & THIS ALLEGED ANTICANCER DRUG HAS ALSO BEEN RESPONSIBLE FOR HUMAN CYANIDE POISONING.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

苦杏仁苷口服给药后小鼠体内最高氰化物水平在大约1.5-2小时达到，并且与氰化钾给药后的值范围相似。评估了消化道各个区域内容物以及肿瘤组织从苦杏仁苷中释放氰化物的能力。胃和上肠的活动很少，而下半肠和粪便释放了大量的氰化物。小鼠之间的差异很大。

THE MAX CYANIDE LEVEL AFTER ORAL ADMIN OF AMYGDALIN TO MICE WAS REACHED AT ABOUT 1 1/2-2 HR & WAS WITHIN THE RANGE OF VALUES SEEN AFTER KCN ADMIN. THE ABILITY OF THE CONTENTS OF VARIOUS REGIONS OF THE GI TRACT & OF TUMOR TISSUE TO RELEASE CYANIDE FROM AMYGDALIN WAS ASSESSED. THE STOMACH & UPPER INTESTINE HAD LITTLE ACTIVITY WHILE THE LOWER INTESTINE & FECES RELEASED LARGE AMOUNTS. THERE WAS A LARGE VARIATION BETWEEN MICE.

来源:Hazardous Substances Data Bank (HSDB)

文献信息

• Compositions and methods for treating infectious disease
  申请人：Sichtnik Laszlo

  公开号：US10183964B2

  公开（公告）日：2019-01-22

  Provided are cyanogenic compositions for treating diseases, such as infectious diseases.

  本发明提供了用于治疗疾病（如传染性疾病）的生氰组合物。
• COMPOSITIONS AND METHODS FOR TREATING INFECTIOUS DISEASE
  申请人：Sichtnik, Laszlo

  公开号：EP2968377B1

  公开（公告）日：2020-07-22
• [EN] COMPOSITIONS AND METHODS FOR TREATING INFECTIOUS DISEASE<br/>[FR] COMPOSITIONS ET MÉTHODES POUR TRAITER UNE MALADIE INFECTIEUSE
  申请人：SICHTNIK LASZLO

  公开号：WO2014165057A1

  公开（公告）日：2014-10-09

  Provided are cyanogenic compositions for treating infectious diseases.