5,6-反式-卡泊三醇 | 113082-99-8

• 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
• 中文名称: 5,6-反式-卡泊三醇
• 中文别名: 反式钙泊三醇
• 英文名称: PRI-2205
• 英文别名: (5E)-Calcipotriol；(1R,3S,5E)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS: 113082-99-8
• 化学式: C₂₇H₄₀O₃
• 分子量: 412.613
• InChiKey: LWQQLNNNIPYSNX-GMGGYIQASA-N

物化性质

• 沸点：
  582.0±50.0 °C(Predicted)
• 密度：
  1.12
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

ADMET

毒理性

• 在妊娠和哺乳期间的影响

哺乳期使用概述：目前没有关于哺乳期间使用钙泊三醇的信息。由于局部应用后吸收不良，钙泊三醇对哺乳婴儿的风险可能较低，通常认为在哺乳期间使用是可以接受的，甚至可以应用于乳头区域。避免将含有倍他米松（恩斯提拉）的复合产品应用于乳房。只有水溶性乳膏或凝胶产品应应用于乳房，因为软膏可能会使婴儿通过舔舐接触到高水平的矿物石蜡。 对哺乳婴儿的影响：截至修订日期，没有找到相关的已发布信息。 对泌乳和母乳的影响：截至修订日期，没有找到相关的已发布信息。

◉ Summary of Use during Lactation:No information is available on the use of calcipotriene during breastfeeding. Because it is poorly absorbed after topical application, calcipotriene is probably a low risk to the nursing infant and is generally considered acceptable during breastfeeding, even to the nipple area. Avoid application of the combination product containing betamethasone (Enstilar) to the breast. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking. ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性成分 Calcipotriol Impurity C 是钙泊三醇的一种杂质。

反应信息

• 作为反应物：
  描述：

  5,6-反式-卡泊三醇 在 9-乙酰基蒽 作用下， 以 丙酮 为溶剂， 生成 卡泊三醇
  参考文献：
  名称：

  Method for preparing analogue of vitamin D

  摘要：

  揭示了一种制备C1，C24-二羟基维生素D类似物的方法。特别是在这里揭示了从维生素D2起始物质制备钙醇和他卡尔西醇的方法。钙醇（化合物1(a)）和他卡尔西醇（化合物1(b)）可以通过本发明的方法合成。此外，使用该方法合成钙醇只需要九个步骤。同样，使用本方法合成他卡尔西醇只需要十个步骤。因此，本方法具有更少的工艺步骤和更高的产量，相对于传统方法而言，代表了一种改进。

  公开号：

  US20070088007A1
• 作为产物：
  描述：

  (E,1S,4R)-4-[(1R,3aS,5E,7aR)-5-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,4,6,7-hexahydro-1H-inden-1-yl]-1-cyclopropylpent-2-en-1-ol 生成 5,6-反式-卡泊三醇
  参考文献：
  名称：

  CALVERLEY, MARTIN J., TETRAHEDRON, 43,(1987) N 20, 4609-4619

  摘要：

  DOI：

文献信息

• Process for Preparation of Pharmaceutically Pure Anhydrous Calcipotriol
  申请人：Kutner Andrzej

  公开号：US20080214876A1

  公开（公告）日：2008-09-04

  A process for the preparation of a pharmaceutical-grade anhydrous calcipotriol comprising: (a) dissolving crude calcipotriol having a water content of X % by weight in a first solvent or in a mixture of two or more first solvents, said first solvent or said mixture of two or more first solvents forming an azeotropic system with water, to obtain a solution of crude calcipotriol; (b) obtaining an intermediate calcipotriol by (i) placing said solution of crude calcipotriol under a reduced pressure and evaporating, if X is greater than or equal to 1, or (ii) crystallizing, if X is lower than 1; and (c) re-dissolving said intermediate calcipotriol in a second solvent or a mixture of two or more second solvents, said second solvent being anhydrous, and crystallizing at least once to obtain pharmaceutical-grade anhydrous calcipotriol.
• COMBINED THERAPY OF COLORECTAL CARCINOMA
  申请人：Wietrzyk Joanna

  公开号：US20120101057A1

  公开（公告）日：2012-04-26

  The invention relates to a combined therapy, wherein addition of a vitamin D analogue to the standard treatment regimen based on cytostatics, 5-fluorouracil and/or its precursors, generates potential possibility of achieving beneficial therapeutic effect in the first-line chemotherapy or adjuvant therapy of colorectal carcinoma. Vitamin D analogues are selected from a group consisting of tacalcitol, calcipotriol and 5,6-trans-isomer of calcipotriol.
• US7700580B2
  申请人：——

  公开号：US7700580B2

  公开（公告）日：2010-04-20
• [EN] USE OF ANASTROZOLE AND VITAMIN D ANALOGUE IN THE COMBINED THERAPY OF BREAST CANCER<br/>[FR] UTILISATION D'ANASTROZOLE ET D'ANALOGUE DE VITAMINE D DANS POLYTHÉRAPIE CONTRE LE CANCER DU SEIN
  申请人：INST FARMACEUTYCZNY

  公开号：WO2012128653A1

  公开（公告）日：2012-09-27

  The invention relates to the use of anastrozole and vitamin D analogues in combined therapy of breast cancer. Vitamin D analogues are selected from a group including calcipotriol, tacalcitol and (1S,3R,5E,7E,22E,24S)-24-cyclopropyl-9,10-secochola- 5,7,10(19),22-tetraen-l,3,24-triol (isomer 5,6-trans of calcipotriol).
• [EN] THE USE OF VITAMIN D ANALOGUES IN COMBINATION WITH IMATINIB IN THERAPY OF NON-SMALL CELL LUNG CANCER<br/>[FR] UTILISATION D'ANALOGUES DE VITAMINE D COMBINÉS À L'IMATINIB EN THÉRAPIE DU CANCER DU POUMON NON À PETITES CELLULES
  申请人：INST FARMACEUTYCZNY

  公开号：WO2013100772A1

  公开（公告）日：2013-07-04

  Use of vitamin D analogues selected from tacalcitol and (lS,3R,5E,7E,22E,24S)-24-cyclopropyl-9,10-secochola-5, 7,10(19),22-tetraen-1,3,24-triol (5,6-trans-calcipotriol) in combination with tyrosine kinase inhibitor imatinib in treatment of non-small cell lung cancer.