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9-氟-11beta,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮 17-丙酸酯 | 5534-13-4

中文名称
9-氟-11beta,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮 17-丙酸酯
中文别名
17-丙酸倍他米松;9-氟-11beta,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮17-丙酸酯;丙酸氯倍米松杂质A;二丙酸倍他米松EP杂质B
英文名称
Betamethasone propionate
英文别名
betamethasone 17-monopropionate;betamethasone 17-propionate;betamethasone-17-propionate;betamethasone;[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
9-氟-11beta,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮 17-丙酸酯化学式
CAS
5534-13-4
化学式
C25H33FO6
mdl
——
分子量
448.532
InChiKey
ITYMTTQVNYAJAA-XGQKBEPLSA-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

物化性质

  • 熔点:
    233-235°C
  • 沸点:
    579.5±50.0 °C(Predicted)
  • 密度:
    1.28±0.1 g/cm3(Predicted)
  • 溶解度:
    DMSO(微溶,加热)、甲醇(微溶)

计算性质

  • 辛醇/水分配系数(LogP):
    2.6
  • 重原子数:
    32
  • 可旋转键数:
    5
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.72
  • 拓扑面积:
    101
  • 氢给体数:
    2
  • 氢受体数:
    7

安全信息

  • WGK Germany:
    3
  • 储存条件:
    2-8°C

SDS

SDS:804818714a74ea27167ce179f557a98a
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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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    9-氟-11beta,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮 17-丙酸酯四氢呋喃 为溶剂, 50.0~80.0 ℃ 、60.0 kPa 条件下, 反应 8.0h, 生成 倍他米松二丙酸酯
    参考文献:
    名称:
    一种倍他米松17α-丙酸酯的制备方法
    摘要:
    一种倍他米松17α‑丙酸酯的制备方法,采用倍他米松与原丙酸三乙酯反应,所述的反应在在四氢呋喃溶剂中进行且采用对甲苯磺酸作为催化剂,反应完成后,不经出料,直接在同一溶剂体系下,向体系中滴加三氯化铝溶液,滴加完毕后,保温反应,反应完毕后,经过后处理工艺得到倍他米松17α‑丙酸酯。本发明在解决倍他米松17α‑丙酸酯采用二氧六环或者二甲基甲酰胺或者其他溶剂等做反应溶剂的同时,还简化了制造流程、提高了收率和纯度。
    公开号:
    CN110003299A
  • 作为产物:
    参考文献:
    名称:
    Correlation between metabolism of betamethasone 17,21-dipropionate and adrenal hypertrophy in rat fetuses
    摘要:
    The effects of metabolites of betamethasone 17,21-dipropionate (BMDP) on the hypothalamo-pituitary-adrenocortical axis were assessed by measurements of adrenal weights, after studying the metabolism of BMDP in vivo and in vitro in pregnant rats and mice. After BMDP was injected intravenously at a dose of 5 mg/kg into rats and mice in late stages of pregnancy, it disappeared rapidly from the plasma and brain stages of pregnancy, it disappeared rapidly from the plasma and brain in both mothers and fetuses while betamethasone 17-propionate (BMP) was detected as the main metabolite followed by betamethasone (BM). In vitro studies demonstrated that BMDP was metabolized to BMP in maternal and fetal tissues (plasma, liver, brain and placenta) of both species. The subcutaneous administration of BMP to rats in the late stages of pregnancy induced adrenal hypertrophy in fetuses, though the adrenals of the mothers became atrophic. In the case of mice, both maternal and fetal adrenals became atrophic. Administration of BM produced adrenal atrophy in mothers and fetuses of both species. The subcutaneous administration of 6 beta-hydroxybetamethasone 17-propionate (6 beta-OH-BMP) to rat fetuses in utero produced adrenal hypertrophy and 6 beta-hydroxybetamethasone (6 beta-OH-BM) showed no effect. These data suggest that BMP is transferred across the placental barrier to produce marked adrenal hypertrophy in rat fetuses.
    DOI:
    10.1016/s0039-128x(81)90348-2
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文献信息

  • Studies on topical antiinflammatory agents. IV. 21-(Alkylthio)acetates and (Methylthio)methoxides of corticosteroids.
    作者:Morihiro MITSUKUCHI、Tomoyuki IKEMOTO、Minoru TAGUCHI、Shohei HIGUSHI、Satoshi ABE、Hajime YASUI、Katsuo HATAYAMA
    DOI:10.1248/cpb.38.786
    日期:——
    A series of 21-(alkylthio)acetates and 21-(methylthio)methoxides of corticosteroids were synthesized and examined for vasoconstrictive activities. The activities of seven compounds were equal to or greater than that of 9α-fluoro-11β, 21-dihydroxy-16β-methyl-17α-valeryloxy-1, 4-pregnadiene-3, 20-dione (betamethasone 17-valerate, BV). Among them, betamethasone 21-(methylthio)acetate 17-propanoate (2Ca) was found to have the most potent activity, which is superior to that of BV. A structure-activity relationship study revealed that substitution of the 21-hydroxy group of corticosteroids with the (methylthio)acetate function is a useful approach for obtaining potent activity.
    一系列含有21-(烷基)乙酸酯和21-(甲基)甲氧基的皮质类固醇被合成并测试了它们的血管收缩活性。七个化合物的活性等于或超过9α--11β, 21-二羟基-16β-甲基-17α-戊酸酯-1, 4-孕二烯-3, 20-二酮(倍他米松17-戊酸酯,BV)。其中,倍他米松21-(甲基)乙酸酯17-丙酸酯(2Ca)显示出最强的活性,优于BV。结构-活性关系研究表明,将皮质类固醇的21-羟基替换为(甲基)乙酸酯功能是一种有效的方法,用以获得强大的活性。
  • Studies on topical antiinflammatory agents. III. Synthesis of 17.ALPHA.-acyloxy-9.ALPHA.-fluoro-11.BETA.-hydroxy-16.BETA.-methyl-1,4-pregnadiene-3,20-dione 21-thio derivatives and related compounds.
    作者:Morihiro MITSUKUCHI、Tomoyuki IKEMOTO、Minoru TAGUCHI、Shohei HIGUCHI、Satoshi ABE、Hajime YASUI、Katsuo HATAYAMA、Kaoru SOTA
    DOI:10.1248/cpb.37.3286
    日期:——
    beta-methyl-1,4-pregnadiene-3, 20-dione 17-esters and related compounds were synthesized and evaluated as topical antiinflammatory agents. These compounds were prepared by the reaction of 9 alpha-fluoro-11 beta,17 alpha,21-trihydroxy-16 beta-methyl-1,4-pregnadiene-3, 20-dione (betamethasone, I) 17-ester derivatives and various mercapto compounds. A structure-activity relationship study revealed that
    合成了一系列9-α--11β,17α-二羟基-16β-甲基-1,4-孕二烯-3、20-二酮17-酯的21-代衍生物和相关化合物,并将其评估为局部抗炎药代理商。这些化合物是由9个α--11β,17α,21-三羟基-16β-甲基-1,4-孕二烯-3、20-二酮(倍他米松I)17-酯衍生物与各种巯基化合物。结构-活性关系研究表明,在21位的基和在17位的酯基的结构组合有助于血管收缩活性。在这些化合物中,发现21-甲基17-丙酸酯化合物(6)具有最强的活性,比倍他米松17-戊酸酯(BV)更有效。
  • Purification of air sensitive steroids
    申请人:Villa Marco
    公开号:US20090240049A1
    公开(公告)日:2009-09-24
    The present invention provides a purification method for air sensitive steroids, by reacting an amino acid or an analogue thereof with the 21-aldehyde oxidation product of such air sensitive steroids to form an adduct that is separated from the purified air sensitive steroids.
    本发明提供了一种用于空气敏感类固醇的纯化方法,通过将氨基酸或其类似物与这些空气敏感类固醇的21-醛氧化产物反应,形成一个加合物,该加合物与纯化后的空气敏感类固醇分离。
  • PURINONE DERIVATIVE
    申请人:Yamamoto Shingo
    公开号:US20130079327A1
    公开(公告)日:2013-03-28
    Compounds represented by general formula (I) (all of the symbols in the formula conform to the definitions in the Description) are compounds that, in addition to having a Btk-selective inhibitory activity, exhibit an excellent metabolic stability and can avoid hepatotoxicity or the like, and as a consequence can provide safe therapeutic agents for diseases in which B cells or mast cells participate.
    由一般公式(I)表示的化合物(公式中的所有符号符合说明中的定义)是除了具有Btk选择性抑制活性外,还表现出优异的代谢稳定性,可以避免肝毒性或类似情况,从而可以为B细胞或肥大细胞参与的疾病提供安全的治疗药物。
  • 一种二丙酸倍他米松的制备方法
    申请人:重庆华邦胜凯制药有限公司
    公开号:CN112851734A
    公开(公告)日:2021-05-28
    本发明属于化学合成技术领域,具体涉及一种二丙酸倍他米松的制备方法。所述方法为以倍他米松‑17‑丙酸酯为原料和丙酸酐为原料,在4‑二甲氨基吡啶做催化剂的条件下,反应生成二丙酸倍他米松,并采用无乙醇二氯甲烷正己烷精制得到高纯度的二丙酸倍他米松。本发明的制备工艺简单,反应温度适中,无超低温或高温反应;制备中所用溶剂或试剂便宜易得,加料方便,运输储存简单;反应催化剂用量少,收率高,产生的废液少,对环境友好,适合商业化生产。
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