2-脱氧-2-(18F)氟葡萄糖 | 63503-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-脱氧-2-(18F)氟葡萄糖
• 英文名称: 2-deoxy-2-[18F]fluoro-D-glucose
• 英文别名: [18F]FDG；[18F]-Fluorodeoxyglucose；2-[¹⁸F]fluoro-2-deoxyglucose；2-[¹⁸F]fluoro-2-deoxy-D-glucose；FDG；Fludeoxyglucose F-18；(2R,3S,4R,5R)-2-(18F)fluoranyl-3,4,5,6-tetrahydroxyhexanal
• CAS: 63503-12-8
• 化学式: C₆H₁₁FO₅
• 分子量: 181.15
• InChiKey: AOYNUTHNTBLRMT-MXWOLSILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  6

ADMET

代谢

氟代脱氧葡萄糖 F 18 被输送到细胞内，并且以与该组织中葡萄糖利用速率成比例的速率被磷酸化为 [18F]-FDG-6-磷酸盐。[18F]-FDG-6-磷酸盐可能被代谢为 2-脱氧-2-[18F] 氟-6-磷酸-D-甘露糖([18F]FDM-6-磷酸盐)。氟代脱氧葡萄糖 F 18 注射剂可能含有几种杂质（例如，2-脱氧-2-氯-D-葡萄糖（ClDG））。C1DG 的生物分布和代谢被认为与氟代脱氧葡萄糖 F 18 相似，并且预期会在细胞内形成 2-脱氧-2-氯-6-磷酸-D-葡萄糖（C1DG-6-磷酸盐）和 2-脱氧-2-氯-6-磷酸-D-甘露糖（ClDM-6-磷酸盐）。磷酸化的脱氧葡萄糖化合物被去磷酸化，产生的化合物（FDG、FDM、C1DG 和 ClDM）可能通过被动扩散离开细胞。

Fludeoxyglucose F 18 is transported into cells and phosphorylated to [18F]-FDG-6-phosphate at a rate proportional to the rate of glucose utilization within that tissue. [18F]-FDG-6-phosphate presumably is metabolized to 2-deoxy-2-[18F] fluoro-6-phospho-Dmannose ([18F]FDM-6-phosphate). Fludeoxyglucose F 18 Injection may contain several impurities (e.g., 2-deoxy-2-chloro-D-glucose (ClDG)). Biodistribution and metabolism of C1DG are presumed to be similar to Fludeoxyglucose F 18 and would be expected to result in intracellular formation of 2-deoxy-2-chloro-6-phospho-D-glucose (C1DG-6-phosphate) and 2-deoxy-2-chloro-6-phospho-D-mannose (ClDM-6-phosphate). The phosphorylated deoxyglucose compounds are dephosphorylated and the resulting compounds (FDG, FDM, C1DG, and ClDM) presumably leave cells by passive diffusion.

来源:DrugBank

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用概述：本记录中的信息指的是将氟脱氧葡萄糖 F18（氟代脱氧葡萄糖 F18；18F-FDG）用作诊断剂。在母乳喂养期间，使用18F FDG进行正电子发射断层扫描（PET）可能比其他类型的扫描更为可取，因为辐射水平低且消失迅速。 在PET扫描后，排入母乳中的18F-FDG量低于对哺乳婴儿的关注水平，大多数国际辐射安全组织表示无需中断母乳喂养。然而，为了遵循将暴露“尽可能合理地降低”的原则，一些指南建议暂停哺乳1到4小时，产品标签建议母亲在注射氟脱氧葡萄糖 F 18 后至少9小时内泵奶并丢弃，避免与婴儿近距离（乳房）接触。担心自己乳汁中放射性水平的母亲可以要求在医院核医学科进行检测。当放射性水平安全时，她可以恢复哺乳。已经发布了一种测量乳汁放射性和确定母亲可以安全恢复哺乳时间的方法。 哺乳可能会导致乳房过度摄取18F FDG。一些作者建议避免在哺乳期妇女的乳房上进行18F FDG成像，以避免假阳性结果。由于哺乳乳房的广泛摄取和由此产生的外部辐射，哺乳母亲应避免在一段时间内与婴儿长时间密切接触。一些作者建议在哺乳母亲进行18F-FDG PET扫描后，婴儿应由第三方用挤出的母乳通过奶瓶喂养1次或4到12小时，具体取决于剂量。 哺乳母亲不应在其工作场所处理PET扫描中使用的放射性物质。 ◉ 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。 ◉ 对哺乳和母乳的影响：截至修订日期，没有找到相关的已发布信息。

◉ Summary of Use during Lactation:Information in this record refers to the use of fludeoxyglucose F18 (fluorodeoxyglucose F18; 18F-FDG) as a diagnostic agent. The use of 18F FDG in positron emission tomography (PET) scans may be preferable to other types of scans during breastfeeding because of the low levels and rapid disappearance of radiation. The amounts of 18F-FDG excreted in breastmilk after a PET scan are below the level of concern for the breastfed infant and most international radiation safety organizations state that no interruption of breastfeeding is necessary. However, to follow the principle of keeping exposure "as low as reasonably achievable", some guidelines recommend withholding breastfeeding for 1 to 4 hours, and product labeling recommends that mothers pump and discard breastmilk and avoid close (breast) contact with the infant for at least 9 hours after the administration of fludeoxyglucose F 18 Injection. Mothers concerned about the level of radioactivity in their milk could ask to have it tested at a nuclear medicine facility at their hospital. When the radioactivity is at a safe level, she may resume breastfeeding. A method for measuring milk radioactivity and determining the time when a mother can safely resume breastfeeding has been published. Lactation can result in excessive uptake of 18F FDG in the breast. Some authors recommend avoiding 18F FDG imaging of the breasts in women who are lactating to avoid false-positive results. Because of extensive uptake by lactating breasts and the consequent external radiation, nursing mothers should refrain from prolonged close contact with their infants for a period of time. Some authors suggest that the infant be bottle fed with expressed breastmilk by a third person for 1 feeding or 4 to 12 hours, depending on the dose, after a PET scan with 18F-FDG in a nursing mother. Nursing mothers should not work with radioactive substances used in PET scans in their workplace. ◉ 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)

毒理性

• 蛋白质结合

氟代脱氧葡萄糖F 18与血浆蛋白的结合程度尚不清楚。

The extent of binding of Fludeoxyglucose F 18 to plasma proteins is not known.

来源:DrugBank

吸收、分配和排泄

• 吸收

氟代脱氧葡萄糖 F 18 注射液在静脉给药后迅速分布到全身所有器官。

Fludeoxyglucose F 18 Injection is rapidly distributed to all organs of the body after intravenous administration.

来源:DrugBank

吸收、分配和排泄

• 排除途径

氟代脱氧葡萄糖 F 18 在 24 小时内从大多数组织中清除，并且可以不改变形态通过尿液排出体外。

Fludeoxyglucose F 18 is cleared from most tissues within 24 hours and can be eliminated from the body unchanged in the urine.

来源:DrugBank

吸收、分配和排泄

• 分布容积

氟代脱氧葡萄糖 F 18 注射液在静脉给药后迅速分布到全身所有器官。

Fludeoxyglucose F 18 Injection is rapidly distributed to all organs of the body after intravenous administration.

来源:DrugBank

吸收、分配和排泄

• 清除

氟代脱氧葡萄糖 F 18 及相关化合物在给药后3到24小时内从非心脏组织中清除。从心肌组织中清除可能需要超过96小时。

Fludeoxyglucose F 18 and related compounds are cleared from non-cardiac tissues within 3 to 24 hours after administration. Clearance from the cardiac tissue may require more than 96 hours

来源:DrugBank

反应信息

• 作为反应物：
  描述：

  2-脱氧-2-(18F)氟葡萄糖 在 sodium hypochlorite 、 4-乙酰氨-2,2,6,6-四甲基哌啶-1-氧 、 sodium bromide 作用下， 生成 2-[¹⁸F]fluoro-2-deoxyglucaric acid
  参考文献：
  名称：

  [EN] IMAGING AGENTS AND METHODS OF USE
  [FR] AGENTS D'IMAGERIE ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2018102574A9
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-[18F]fluoro-D-glucopyranose 在 sodium hydroxide 、 tC₁₈ SepPak cartridge 作用下， 生成 2-脱氧-2-(18F)氟葡萄糖
  参考文献：
  名称：

  Kim, H. W.; Jeong, J. M.; Lee, D. S., Journal of labelled compounds and radiopharmaceuticals, 2003, vol. 46, p. S217 - S217

  摘要：

  DOI：

文献信息

• Radio-labeled compounds, compositions, and methods of making the same
  申请人：Frangioni V. John

  公开号：US20060083678A1

  公开（公告）日：2006-04-20

  18 F radio-labeled compounds, methods of making the radio-labeled compounds, and applications of the same are disclosed.

  揭示了18F放射性标记化合物、制备该放射性标记化合物的方法以及其应用。
• Application of [18F]FDG in radiolabeling reactions using microfluidic technology
  作者：Vincent R. Bouvet、Frank Wuest

  DOI：10.1039/c3lc50797a

  日期：——

  Radiolabeling of peptides with the short-lived positron emitter fluorine-18 is usually a challenging endeavour. Conventional radiolabeling reactions mostly require fairly large amounts of peptides as labeling precursors, and extensive synthesis times. Intrinsic advantages of microfluidic technology permit to overcome these hurdles. Herein, we describe how microfluidic technology combined with [18F]FDG as readily available PET radiotracer allows for fast and high yielding radiolabeling reactions of peptides with fluorine-18.

  用短寿命正电子发射体氟-18 对肽进行放射性标记通常是一项具有挑战性的工作。传统的放射性标记反应大多需要相当大量的肽作为标记前体，而且合成时间较长。微流控技术的内在优势可以克服这些障碍。在此，我们将介绍微流控技术如何与[18F]FDG（现成的 PET 放射性示踪剂）相结合，快速、高产地实现多肽与氟-18 的放射性标记反应。
• Facile synthesis of 2‐deoxy‐2‐[ ¹⁸ F]fluorosorbitol using sodium borohydride on aluminum oxide
  作者：Koki Hasegawa、Kazuhiro Koshino、Takahiro Higuchi

  DOI：10.1002/jlcr.3887

  日期：2021.1

  2-Deoxy-2-[18 F]fluorosorbitol (18 F-FDS) has become increasingly useful in functional renal imaging. FDS is synthesized by the one-step reduction of 2-deoxy-2-[18 F]fluoroglucose (18 F-FDG). To develop a more simple and rapid procedure for 18 F-FDS synthesis, we examined reduction reactions with solid-supported NaBH4 . Synthetic yields using BH4 -IRA400 (polymer-based matrix) and NaBH4 -Al2 O3 (clay-based

  2-Deoxy-2-[18 F] 氟山梨糖醇 (18 F-FDS) 在功能性肾脏成像中越来越有用。FDS 是通过一步还原 2-脱氧-2-[18 F] 氟葡萄糖 (18 F-FDG) 合成的。为了开发更简单、更快速的 18 F-FDS 合成程序，我们研究了固体负载的 NaBH4 的还原反应。比较了使用 BH4 -IRA400（基于聚合物的基质）和 NaBH4 -Al2 O3（基于粘土的基质）作为固载试剂的合成产率。发现 NaBH4 -Al2 O3 在 FDG 还原反应中远优于 BH4 -IRA400。IRA 400 不适合该反应，因为它除了吸附葡萄糖外还吸附 FDG，而在使用 BH4 -IRA400 时没有合成 FDS。相比之下，NaBH4 -Al2 O3 只需要过滤作为后处理，在总共 10 分钟后以 90% 的产率提供 FDS。氧化铝上的 NaBH4 在反应中很容易在 1 分钟内消耗掉，无
• Fast [18F]FDG synthesis by alkaline hydrolysis on a low polarity solid phase support
  作者：C. Lemaire、Ph. Damhaut、B. Lauricella、C. Mosdzianowski、J.-L Morelle、M. Monclus、J. Van Naemen、E. Mulleneers、J. Aerts、A. Plenevaux、C. Brihaye、A. Luxen

  DOI：10.1002/jlcr.572

  日期：2002.4

  The synthesis of 2-deoxy-2-[18F]fluoro-D-glucose ([18F]FDG) has been simplified by the use of a tC18 Sep Pak cartridge to effect purification and hydrolysis of the tetraacetylated [18F]fluoro-glucose compound ([18F]TAG). After radiolabelling, this derivative was trapped on a solid phase extraction (SPE) cartridge and the residual reaction solvent (CH3CN), reagents (K222, K2CO3,…) and by-products removed by washing the support with water. After this cleaning step, the acetyl groups were cleaved on the same tC18 column using 2N sodium hydroxide. This fast reaction proceeded near quantitatively (>98%) at room temperature in less than 2 min. The [18F]FDG was then recovered with a small amount of water, neutralized with a slight excess of 2N hydrochloric acid, buffered for pH with a citrate solution and finally purified on a neutral alumina oxide and a second tC18 column. After filtration, the radiochemical yield of this [18F]FDG isotonic solution after more than 100 production runs was found to be very reliable and reproducible (70±6% decay corrected). The synthesis time was about 22 min. Quality controls showed that the radiochemical purity was higher than 98% and in any case no [18F]FDM was detected. Only traces of 2-chloro-2-deoxy-glucose (ClDG) were found in the final sample (64±9 μg/ batch of 16 ml). [18F]FDG specific activity averaged between 1 and 20 Ci/µmol (EOS). No evaporation and use of ion retardation resin (AG11A8) are required. Moreover, this new approach is suitable for complete remote operation using available single use medical components. Copyright © 2002 John Wiley & Sons, Ltd.

  2-deoxy-2-[18F]fluoro-D-glucose ([18F]FDG)的合成已通过使用 tC18 Sep Pak 滤芯进行纯化和水解四乙酰化[18F]氟葡萄糖化合物 ([18F]TAG)而得到简化。进行放射性标记后，将这种衍生物截留在固相萃取（SPE）滤芯上，然后用水清洗支撑物，去除残留的反应溶剂（CH3CN）、试剂（K222、K2CO3......）和副产物。清洗步骤结束后，在同一 tC18 色谱柱上使用 2N 氢氧化钠裂解乙酰基。这一快速反应在室温下进行，接近定量（>98%），用时不到 2 分钟。然后用少量水回收[18F]FDG，再用略微过量的 2N 盐酸中和，用柠檬酸盐溶液缓冲 pH 值，最后用中性氧化铝和第二个 tC18 色谱柱纯化。过滤后，经过 100 多次生产后，发现这种[18F]FDG 等渗溶液的放射化学产率非常可靠且可重复（衰变校正为 70±6%）。合成时间约为 22 分钟。质量控制表明，放射化学纯度高于 98%，而且在任何情况下都没有检测到[18F]FDM。在最终样品中只发现了微量的 2-氯-2-脱氧葡萄糖（ClDG）（64±9 μg/批 16 ml）。[18F]FDG的比活度平均在 1 到 20 Ci/µmol（EOS）之间。无需蒸发和使用离子延迟树脂（AG11A8）。此外，这种新方法适合使用现有的一次性医疗元件进行完全远程操作。Copyright © 2002 John Wiley & Sons, Ltd. All Rights Reserved.
• Mosdzianowski; Lemaire; Lauricella, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S515-S516
  作者：Mosdzianowski、Lemaire、Lauricella、Aerts、Morelle、Gobert、Herman、Luxen

  DOI：——

  日期：——