octadecanoic acid-nicotinamide complex | 107864-39-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octadecanoic acid-nicotinamide complex
• 英文别名: Octadecanoic acid;pyridine-3-carboxamide
• CAS: 107864-39-1
• 化学式: C₆H₆N₂O*C₁₈H₃₆O₂
• 分子量: 406.609
• InChiKey: NSYRRLCSLVTAAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  octadecanoic acid-nicotinamide complex 生成 烟酰胺
  参考文献：
  名称：

  Release Kinetics of Nicotinamide form Fatty Acid-Nicotinamide Equimolar Complexes. II. Activation Thermodynamic Quantities.

  摘要：

  测定了脂肪酸（FA）-NAA 复合物（FA-NAA）在不同温度下释放烟酰胺（NAA）的速率，并估算了释放 NAA 的热力学量。研究结果与之前对脂肪酸-二硫化二胺（TDS）复合物 (FA)6(TDS) 的研究结果进行了比较。FA-NAA 释放 NAA 的活化焓（ΔH〓）和活化熵（ΔS〓）值分别为正值和负值，这表明从焓和熵的角度来看，释放 NAA 都是不利的。ΔH〓与组成 FA 的碳数（n）的关系图显示了一条奇数位置向上凸起的之字形线，Δ〓和ΔH〓的绝对值的极值也显示了一条之字形线；无论是偶数还是奇数 FA，随着 n 的增大，ΔH〓的正值增大，ΔS〓的负值减小。研究发现，与偶数 FA 形成的 FA-NAA 相比，奇数 FA 形成的 FA-NAA 释放 NAA 更不利于助长，但更有利于助长。这一现象与在 (FA)6(TDS) 中观察到的现象相似。此外，这表明 FA-NAA 至少是通过范德华力和疏水相互作用形成的，范德华力在奇数 FA 形成的 FA-NAA 中占主导地位，而疏水相互作用在偶数 FA 形成的 FA-NAA 中占主导地位。

  DOI：

  10.1248/cpb.39.3114
• 作为产物：
  描述：

  烟酰胺 、 硬脂酸 以 1,2-二氯乙烷 为溶剂， 生成 octadecanoic acid-nicotinamide complex
  参考文献：
  名称：

  A new complex composed of nicotinamide and octadecanoic acid.

  摘要：

  分离出一种由烟酰胺（NAA）和十八烷酸（C18）组成的新型晶体复合物。通过元素分析和定量分析确定了该复合物的组成。发现该复合物的化学计量比为（C18）6（NAA）5。

  DOI：

  10.1248/cpb.39.1634

文献信息

• Release of Nicotinamide from Fatty Acid-Nicotinamide Equimolar Complexes.
  作者：Shoko YOKOYAMA、Fumio UEDA、Tadao FUJIE

  DOI：10.1248/cpb.39.3075

  日期：——

  The release behavior of nicotinamide (NAA) from fatty acid (FA)-NAA equimolar complexes was examined in a JP XI dissolution test apparatus in JP XI disintegration test medium No. 1 (pH 1.2) at 37°C where the carbon number of FA is 14-18. The time required for 50% or 80% of NAA to release (T50 or T80) was measured, and the effect of the constituent FA on T50 or T80 was investigated. The values of T50 or T80 for FA-NAA formed with odd-numberd FA were larger than those for FA-NAA formed with even-numbered FA whose alkyl chain length is one more carbon number longer, though the values of T50 of T80 increased rather regularly with an increase of the alkyl chain length for only even-numbered or odd-numbered FA. The values of T50 and T80 for FA-NAA formed with heptadecanoic acid (C17-NAA) were about 36 and 102 min, respectively, suggesting that C17-NAA may be applicable to the preparetion of a sustained-release drug formulation.

  在脂肪酸（FA）-NAA 等摩尔复合物中检测了烟酰胺（NAA）在 JP XI 溶出试验设备中的释放行为，该设备采用 JP XI 1 号崩解试验培养基（pH 值为 1.2），温度为 37°C，其中 FA 的碳数为 14-18。测量了 50%或 80% NAA 释放所需的时间（T50 或 T80），并研究了成分 FA 对 T50 或 T80 的影响。奇数 FA 形成的 FA-NAA 的 T50 或 T80 值大于烷基链长多一个碳数的偶数 FA 形成的 FA-NAA 的 T50 或 T80 值。与十七酸（C17-NAA）形成的 FA-NAA 的 T50 值和 T80 值分别约为 36 分钟和 102 分钟，这表明 C17-NAA 可能适用于制备缓释药物制剂。
• Release Kinetics of Nicotinamide from Fatty Acid-Nicotinamide Equimolar Complexes. I. Release Characteristics of Fatty Acid Complexes.
  作者：Shoko YOKOYAMA、Fumio UEDA、Tadao FUJIE

  DOI：10.1248/cpb.39.2696

  日期：——

  The rates of release of nicotinamide (NAA) from fatty acid (FA)-NAA complexes, FA-NAA, were determined in a JP XI dissolution test apparatus in 500 ml of JP XI disintegration test medium No. 1 at 37°C. The release rate constant (k) and the activation Gibbs energy (ΔG〓) for the release of NAA from FA-NAA were estimated. The results obtained for FA-NAA were compared with previous results obtained for the thiamine disulfide (TDS) complex, (FA)6-(TDS).The plots of log k against the carbon number of the constituent FA (n) presented a zig-zag line which indicates a downward convex at an odd-numbered position. The plots of ΔG〓 against n showed a zig-zag line with an upward convex at an odd-numbered position, though the positive value of ΔG〓 increased rather regularly with an increase of n for either even-numbered or odd-numbered FA.The phonomena that the plots of log k vs. n and ΔG〓 vs. show zig-zag lines due to the difference between even- and odd-numbered FA were the same as observed previously for the relase of TDS from (FA)6 (TDS).

  烟酰胺(NAA)从脂肪酸(FA)-NAA复合物(FA-NAA)的释放速率在JP XI溶出测试装置中在500ml JP XI崩解测试介质No.1中在37℃下测定。估计了 FA-NAA 释放 NAA 的释放速率常数 (k) 和活化吉布斯能 (ΔG〓)。将 FA-NAA 获得的结果与之前获得的二硫化硫胺 (TDS) 复合物 (FA)6-(TDS) 的结果进行比较。log k 相对于组成 FA (n) 的碳原子数的图呈现出锯齿形-zag 线，表示奇数位置处的向下凸形。 ΔG〓 对 n 的图显示出在奇数位置处向上凸的锯齿形线，尽管对于偶数或奇数 FA，ΔG〓 的正值随着 n 的增加而相当规律地增加。由于偶数和奇数 FA 之间的差异，log k vs. n 和 ΔG〓 vs. 图显示锯齿线的现象与之前观察到的 (FA)6 的 TDS 释放相同（ TDS）。
• Pharmaceutical co-crystal compositions
  申请人：Almarsson Orn

  公开号：US20070026078A1

  公开（公告）日：2007-02-01

  A pharmaceutical composition comprising a co-crystal of an API and a co-crystal former; wherein the API has at least one functional group selected from ether, thioether, alcohol, thiol, aldehyde, ketone, thioketone, nitrate ester, phosphate ester, thiophosphate ester, ester, thioester, sulfate ester, carboxylic acid, phosphonic acid, phosphinic acid, sulfonic acid, amide, primary amine, secondary amine, ammonia, tertiary amine, sp2 amine, thiocyanate, cyanamide, oxime, nitrile diazo, organohalide, nitro, s-heterocyclic ring, thiophene, n-heterocyclic ring, pyrrole, o-heterocyclic ring, furan, epoxide, peroxide, hydroxamic acid, imidazole, pyridine and the co-crystal former has at least one functional group selected from amine, amide, pyridine, imidazole, indole, pyrrolidine, carbonyl, carboxyl, hydroxyl, phenol, sulfone, sulfonyl, mercapto and methyl thio, such that the API and co-crystal former are capable of co-crystallizing from a solution phase under crystallization conditions.

  一种药物组合物，包括API和共晶形成剂的共晶体；其中，API具有至少一种从醚，硫醚，醇，硫醇，醛，酮，硫酮，硝酸酯，磷酸酯，硫代磷酸酯，酯，硫酯，硫酸酯，羧酸，膦酸，亚磷酸，磺酸，酰胺，一级胺，二级胺，氨，三级胺，sp2胺，硫氰酸盐，氰胺，肟，腈，重氮，有机卤化物，硝基，s-杂环环，噻吩，n-杂环环，吡咯，o-杂环环，呋喃，环氧化物，过氧化物，羟肟酸，咪唑，吡啶中至少一种官能团，而共晶形成剂具有至少一种从胺，酰胺，吡啶，咪唑，吲哚，吡咯烷，羰基，羧基，羟基，酚，磺酰，磺酰基，巯基和甲硫基中选择的官能团，使得API和共晶形成剂能够在结晶条件下从溶液相共结晶。
• Pharmaceutical Co-Crystal Compositions
  申请人：Almarsson Orn

  公开号：US20100311701A1

  公开（公告）日：2010-12-09

  A pharmaceutical composition comprising a co-crystal of an API and a co-crystal former; wherein the API has at least one functional group selected from ether, thioether, alcohol, thiol, aldehyde, ketone, thioketone, nitrate ester, phosphate ester, thiophosphate ester, ester, thioester, sulfate ester, carboxylic acid, phosphonic acid, phosphinic acid, sulfonic acid, amide, primary amine, secondary amine, ammonia, tertiary amine, imine, thiocyanate, cyanamide, oxime, nitrile diazo, organohalide, nitro, S-heterocyclic ring, thiophene, N-heterocyclic ring, pyrrole, O-heterocyclic ring, furan, epoxide, peroxide, hydroxamic acid, imidazole, pyridine and the co-crystal former has at least one functional group selected from amine, amide, pyridine, imidazole, indole, pyrrolidine, carbonyl, carboxyl, hydroxyl, phenol, sulfone, sulfonyl, mercapto and methyl thio, such that the API and co-crystal former are capable of co-crystallizing from a solution phase under crystallization conditions.

  一种药物组合物，包括API和共晶形成剂的共晶体；其中API具有至少一种功能基团，所述功能基团包括醚、硫醚、醇、巯基、醛、酮、硫酮、硝酸酯、磷酸酯、硫代磷酸酯、酯、硫酯、硫酸酯、羧酸、膦酸、亚磷酸、磺酸、酰胺、一级胺、二级胺、氨、三级胺、亚胺、硫氰酸盐、氰胺、肟、腈、重氮、有机卤化物、硝基、S-杂环环、噻吩、N-杂环环、吡咯、O-杂环环、呋喃、环氧化物、过氧化物、羟肟酸、咪唑和吡啶；共晶形成剂具有至少一种功能基团，所述功能基团包括胺、酰胺、吡啶、咪唑、吲哚、吡咯烷、羰基、羧基、羟基、酚、磺酰、磺酰基、巯基和甲基硫，因此，在结晶条件下，API和共晶形成剂能够从溶液相共结晶。
• AYUKAVA, KOITI;XIGASI, MASARU;UEHDA, FUMIO
  作者：AYUKAVA, KOITI、XIGASI, MASARU、UEHDA, FUMIO

  DOI：——

  日期：——