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meta-iodobenzylguanidine | 76924-93-1

中文名称
——
中文别名
——
英文名称
meta-iodobenzylguanidine
英文别名
123I-metaiodobenzylguanidine;MIBG;Iobenguane I-123;2-[(3-(123I)iodanylphenyl)methyl]guanidine
meta-iodobenzylguanidine化学式
CAS
76924-93-1
化学式
C8H10IN3
mdl
——
分子量
271.188
InChiKey
PDWUPXJEEYOOTR-IUAIQHPESA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1
  • 重原子数:
    12
  • 可旋转键数:
    2
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.12
  • 拓扑面积:
    64.4
  • 氢给体数:
    2
  • 氢受体数:
    1

ADMET

毒理性
  • 在妊娠和哺乳期间的影响
◉ 母乳喂养期间使用总结:本记录中的信息是指将碘苯扎胺 I 123(I 123 邻碘苄基胍;I 123 MIBG)用作诊断剂。根据 I 123 的物理半衰期,制造商建议母亲至少泵奶并丢弃 6 天的奶,尽管根据有效半衰期,停奶 3.5 天可能更一致。然而,美国核能管理委员会的一个小组委员会建议,在剂量高达 11 mCi 的情况下,无需停止哺乳。如果停止哺乳,且母亲在检查前已经挤出并保存了奶,她可以在哺乳中断期间喂给婴儿。母亲在哺乳中断期间泵出的奶可以丢弃,或者冷藏储存,并在经过大约 5.5 天或 10 个物理半衰期后喂给婴儿。 担心奶中放射性水平的母亲可以要求在医院核医学科进行检测。当放射性水平达到安全水平时,她可以恢复哺乳。已经发布了一种测量奶中放射性并确定母亲可以安全恢复哺乳的时间的方法。 ◉ 对哺乳婴儿的影响:截至修订日期,未找到相关已发布信息。 ◉ 对泌乳和母乳的影响:截至修订日期,未找到相关已发布信息。
◉ Summary of Use during Lactation:Information in this record refers to the use of iobenguane I 123 (I 123 meta-iodobenzylguanidine; I 123 MIBG) as a diagnostic agent. The manufacturer recommends that mothers should pump and discard milk for at least 6 days based on the physical half-life of I 123, although discontinuation for 3.5 days would be more consistent with the effective half-life. However, a US Nuclear Regulatory Commission subcommittee has recommended that nursing need not be discontinued with doses up to 11 mCi. If breastfeeding is discontinued and the mother has expressed and saved milk prior to the examination, she can feed it to the infant during the period of nursing interruption. The milk that is pumped by the mother during the time of breastfeeding interruption can either be discarded or stored refrigerated and given to the infant after 10 physical half-lives, or about 5.5 days, have elapsed. 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. ◉ 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)

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    3-(trimethylstannyl)benzylguanidine 生成 meta-iodobenzylguanidine
    参考文献:
    名称:
    Process for the preparation of radiolabeled meta-halobenzylguanidine
    摘要:
    本发明提供了一种无载体加入的放射性标记的间位卤代苯基胍的合成方法,其中包括将间位三烷基锡苯基胍与卤素的放射性核素源反应进行卤代锡脱基反应。本发明还提供了作为上述过程中间体的间位三烷基锡苯基胍。
    公开号:
    EP0693467A1
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文献信息

  • Radiosynthesis of SPECT tracers via a copper mediated <sup>123</sup>I iodination of (hetero)aryl boron reagents
    作者:Thomas C. Wilson、Greg McSweeney、Sean Preshlock、Stefan Verhoog、Matthew Tredwell、Thomas Cailly、Véronique Gouverneur
    DOI:10.1039/c6cc07417k
    日期:——

    The Cu-mediated [123I]iodination of aryl boronic pinacol esters and acids exhibits broad scope and is successfully applied to the labelling of four radiotracers, [123I]DPA-713, [123I]IMPY, [123I]MIBG and [123I]IPEB.

    芳基硼酸皮纳科酯和酸的Cu介导的[123I]碘化反应具有广泛的适用范围,并成功应用于四种放射示踪剂的标记,[123I]DPA-713,[123I]IMPY,[123I]MIBG和[123I]IPEB。
  • Large-scale synthesis of no-carrier-added [<sup>123</sup>I]mIBG, using two different stannylated precursors
    作者:Daniel D. Rossouw、Lebohang Macheli
    DOI:10.1002/jlcr.1668
    日期:2009.9.30
    The clinical advantages of no-carrier-added (n.c.a) radioiodinated meta-iodobenzylguanidine ([*I]mIBG) over its carrier-added (c.a.) analogue have previously been reported. A large-scale synthesis of n.c.a. [123I]mIBG was therefore investigated in this study, using a slightly adapted literature method. Two bis (t-butyloxycarbonyl)-protected (bis-Boc) stannylated benzylguanidine precursors were prepared. The bis-Boc-trimethylstannyl precursor was used to optimize radioiodination conditions. N-chlorosuccinimide (NCS) was used as oxidant. An HPLC method was developed to monitor radioiodination and de-protection steps. Amounts of 200 g precursor and 2000 g NCS resulted in HPLC yields of Boc-protected radioiodinated compounds in excess of 90%. De-protection was carried out with trifluoroacetic acid at 110°C. A robust solid phase extraction method was developed to purify reaction mixtures. Radiochemical yields at radioactivity levels ranging between 1900 and 3280 MBq were 85±2.2% (n=4). A twice scaled up reaction at 5340 MBq gave a similar yield. Radiochemical purities were in excess of 98% and the specific activity estimated at approximately 1 TBq.µmol−1. Yields obtained from an HPLC-purified bis-Boc-tributylstannyl precursor were generally lower and ranged from 61 to 81%. Results obtained in this study suggest that n.c.a [123I]mIBG could be synthesized on a GBq scale. Copyright © 2009 John Wiley & Sons, Ltd.
    先前已报道过无载体添加 (n.c.a) 放射性碘标记间碘苄基胍 ([*I]mIBG) 相对于其添加载体 (c.a.) 类似物的临床优势。 n.c.a. 的大规模合成因此,本研究使用稍微改编的文献方法对[123I]mIBG进行了研究。制备了两种双(叔丁氧羰基)保护的(双-Boc)甲锡烷基化的苄基胍前体。双-Boc-三甲基甲锡烷基前体用于优化放射性碘化条件。 N-氯代琥珀酰亚胺(NCS)用作氧化剂。开发了 HPLC 方法来监测放射性碘化和脱保护步骤。 200 g 前体和 2000 g NCS 的量导致 Boc 保护的放射性碘化化合物的 HPLC 产率超过 90%。在110℃下用三氟乙酸进行脱保护。开发了一种强大的固相萃取方法来纯化反应混合物。放射性水平在 1900 至 3280MBq 之间的放射化学产率为 85±2.2% (n=4)。在 5340 MBq 下进行两次放大反应得到了相似的产率。放射化学纯度超过 98%,比活度估计约为 1 TBq.μmol−1。从 HPLC 纯化的双-Boc-三丁基甲锡基前体获得的产率通常较低,为 61% 至 81%。本研究获得的结果表明 n.c.a [123I]mIBG 可以在 GBq 规模上合成。版权所有 © 2009 约翰·威利父子有限公司
  • Process for the preparation of radiolabeled meta-halobenzylguanidine
    申请人:MERCK FROSST CANADA INC.
    公开号:EP0693467A1
    公开(公告)日:1996-01-24
    The present invention provides a no-carrier-added synthesis of radiolabeled meta-halobenzylguanidine by halodestannylation which comprises reacting a meta-trialkylstannylbenzylguanidine with a source of radionuclide of a halogen. The present invention also provides meta-trialkylstannylbenzylguanidine as intermediates in the afore-mentioned process.
    本发明提供了一种无载体加入的放射性标记的间位卤代苯基胍的合成方法,其中包括将间位三烷基锡苯基胍与卤素的放射性核素源反应进行卤代锡脱基反应。本发明还提供了作为上述过程中间体的间位三烷基锡苯基胍。
  • LIGANDS FOR IMAGING CARDIAC INNERVATION
    申请人:Purohit Ajay
    公开号:US20100221182A1
    公开(公告)日:2010-09-02
    Novel compounds that find use as imaging agents within nuclear medicine applications (PET imaging) for imaging of cardiac innervation are disclosed. These PET based radiotracers may exhibit increased stability, decreased NE release (thereby reducing side effects), improved quantitative data, and/or high affinity for VMAT over prior radiotracers. Methods of using the compounds to image cardiac innervation are also provided. In some instances the compounds are developed by derivatizing certain compounds with 18 F in a variety of positions: aryl, alkyl, a keto, benzylic, beta-alkylethers, gamma-propylalkylethers and beta-proplylalkylethers. Alternatively or additionally, a methyl group a is added to the amine, and/or the catechol functionality is either eliminated or masked as a way of making these compounds more stable.
    本发明揭示了一种新型化合物,可用作核医学应用(PET成像)中的成像剂,用于成像心脏神经。这些基于PET的放射性示踪剂可能表现出增加的稳定性,减少NE释放(从而减少副作用),改善定量数据和/或高亲和力,以VMAT优于先前的放射性示踪剂。还提供了使用这些化合物成像心脏神经的方法。在某些情况下,这些化合物是通过在各种位置上衍生化某些化合物与18F而开发出来的:芳基,烷基,酮,苄基,β-烷基醚,γ-丙基烷基醚和β-丙基烷基醚。或者,还可以添加甲基基团到胺中,和/或消除或掩盖儿茶酚的功能,以使这些化合物更加稳定。
  • 一种适合临床应用的无载体[*I]MIBG的制备 方法及应用
    申请人:江苏省原子医学研究所
    公开号:CN104307002B
    公开(公告)日:2017-08-15
    本发明提供了一种适合临床应用的无载体[ * I]MIBG的制备方法,通过将三丁锡基苄胍溶于醇类溶剂中并加入到适量的磷酸缓冲液中冷冻干燥得冻干粉末,然后将所冻干后的粉末加入到含 * I离子的水溶液中,随后加入氧化剂和酸性缓冲液中反应,由于三丁锡基苄胍的冻干粉末不溶于水,因此在反应完成后,可以轻易的去除反应液中未反应的三丁锡基苄胍,得到的[ * I]MIBG不仅收率高,标记率高,而且未反应的锡前体以及反应过后的锡的副产物可以轻易的完全除去,不含杂质,使得制备的无载体[ * I]MIBG可以直接注射于人体内,更加适合于临床应用。
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