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16-methylene-17α-hydroxy-17β-acetyl-19-norandrosta-4-en-3-one | 7690-08-6

中文名称
——
中文别名
——
英文名称
16-methylene-17α-hydroxy-17β-acetyl-19-norandrosta-4-en-3-one
英文别名
nestorone alcohol;Segesterone;16-methylene-17α-hydroxy-19-norpregn-4-ene-3,20-dione;(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-13-methyl-16-methylidene-2,6,7,8,9,10,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-one
16-methylene-17α-hydroxy-17β-acetyl-19-norandrosta-4-en-3-one化学式
CAS
7690-08-6
化学式
C21H28O3
mdl
——
分子量
328.452
InChiKey
SFLXYFZGKSGFKA-XUDSTZEESA-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:
    232-234 °C(Solv: methanol (67-56-1))
  • 沸点:
    497.1±45.0 °C(Predicted)
  • 密度:
    1.16±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.3
  • 重原子数:
    24
  • 可旋转键数:
    1
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.71
  • 拓扑面积:
    54.4
  • 氢给体数:
    1
  • 氢受体数:
    3

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:醋酸赛戈斯特龙在美国以复方阴道避孕环(Annovera)的形式提供,该环释放醋酸赛戈斯特龙和乙炔雌二醇。目前没有关于在哺乳期间使用该产品的信息;然而,赛戈斯特龙口服生物利用度低,因此哺乳婴儿对赛戈斯特龙的全身暴露将最小化。在哺乳期间不需要特别的预防措施。 根据现有证据,美国的专家意见认为,由于凝血风险,不应在产后3周前使用复方避孕产品。在产后3周到6个月之间,使用该方法的好处通常超过了理论上的或已证实的风险,尽管对哺乳无影响的证据不足,且不包括早产或患病婴儿。产后6个月后,可以使用复方避孕药,包括口服片剂、透皮贴剂和阴道环,但如果将继续哺乳,则更推荐仅含孕激素的方法。世界卫生组织的指南更为严格,指出在哺乳母亲中,不应在产后42天前使用复方口服避孕药,在产后6周到6个月之间,使用该方法的不利因素通常超过了有利因素。Annovera的制造商建议在停止哺乳之前使用其他形式的避孕。 ◉ 对哺乳婴儿的影响:截至修订日期,没有找到关于醋酸赛戈斯特龙和乙炔雌二醇阴道插入物的相关已发布信息。关于使用醋酸赛戈斯特龙植入剂的研究发现,对生长和发育没有不良影响。 ◉ 对泌乳和母乳的影响:截至修订日期,没有找到相关已发布信息。
◉ Summary of Use during Lactation:Segesterone acetate is available in the United States in a combination contraceptive vaginal ring (Annovera) that releases segesterone acetate and ethinyl estradiol. No information is available on the use of this product during breastfeeding; however, segesterone is poorly bioavailable orally, so systemic exposure to segesterone in breastfed infants will be minimal. No special precautions are necessary during breastfeeding. Based on the available evidence, expert opinion in the United States holds that because of the clotting risk, combination contraceptive products should not be used before 3 weeks postpartum. Between 3 weeks and 6 months postpartum, the advantages of using the method generally outweigh the theoretical or proven risks, although the evidence of lack of effect on lactation is poor and does not include preterm or ill infants. After 6 months postpartum, combination contraceptives, including oral tablets, the transdermal patch and vaginal ring, can be used, but progestin-only methods are preferred if breastfeeding will be continued. World Health Organization guidelines are more restrictive, stating that combined oral contraceptives should not be used in nursing mothers before 42 days postpartum and the disadvantages of using the method generally outweigh the advantages between 6 weeks and 6 months postpartum. The manufacturer of Annovera recommends that another form of contraception should be used until breastfeeding is discontinued. ◉ Effects in Breastfed Infants:Relevant published information on segesterone acetate and ethinylestradiol vaginal insert was not found as of the revision date. Studies on the use of segesterone acetate implants have found no adverse effects on growth and development. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.
来源:Drugs and Lactation Database (LactMed)

SDS

SDS:838311b26007f5a20c9805f64c3c41dc
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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

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文献信息

  • [EN] PROCESS FOR ALKYNYLATING 16-SUBSTITUTED-17-KETO STEROIDS<br/>[FR] PROCÉDÉ POUR ALCYNYLER DES 17-CÉTO-STÉROÏDES 16-SUBSTITUÉS
    申请人:CRYSTAL PHARMA SAU
    公开号:WO2013092668A1
    公开(公告)日:2013-06-27
    The invention relates to a process for ethynylating 16-methylene-17-keto steroids to the corresponding 16-methylene-17α-ethynyl-17β-hydroxy steroids by treatment with silyl-protected lithium acetylides followed by further desilylation. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as e.g. Nestorone® or melengestrol acetate.
    该发明涉及一种将16-亚甲基-17-酮类固醇乙炔化为相应的16-亚甲基-17α-乙炔基-17β-羟基类固醇的方法,方法是通过与硅保护的锂乙炔基作用,然后进行进一步的去硅化处理。所得产物是制备几种药用活性剂的有用中间体,例如Nestorone®或乙烯孕酮醋酸酯。
  • Method of preparation of ester derivatives of steroids
    申请人:The Population Council, Center for Biomedical Research
    公开号:US05710293A1
    公开(公告)日:1998-01-20
    The present invention relates to a method of using a perchloric acid catalyzed reaction to make acyl derivatives of norprogesterone compounds and, in particular, 16-methylene-17.alpha.-hydroxy-19-norpregn-4-ene-3,20-dione.
    本发明涉及一种利用高氯酸催化反应制备诺醇孕酮化合物的酰基衍生物的方法,特别是16-甲烯基-17α-羟基-19-诺孕-4-烯-3,20-二酮。
  • [EN] PREPARATION OF ESTER DERIVATIVES OF STEROIDS<br/>[FR] PREPARATION D'ESTERS DERIVES DE STEROÏDES
    申请人:THE POPULATION COUNCIL, INC.
    公开号:WO1997013779A1
    公开(公告)日:1997-04-17
    (EN) The present invention relates to a method of using a perchloric acid catalyzed reaction to make acyl derivatives of norprogesterone compounds and, in particular, 16-methylene-17$g(a)-hydroxy-19-norpregn-4-ene-3,20-dione.(FR) Un procédé permet d'utiliser une réaction catalysée par l'acide perchlorique pour produire des dérivés acyle de composés à base de norprogestérone, et en particulier 16-méthylène-17$g(a)-hydroxy-19-norprègne-5-ène-3,20-dione.
    (中) 本发明涉及一种使用高氯酸催化反应制备诺孕酮化合物的酰基衍生物的方法,特别是16-甲烯-17$g(a)-羟基-19-去甲孕-4-烯-3,20-二酮。
  • Method of providing birth control
    申请人:The Population Council, Inc.
    公开号:US10632066B1
    公开(公告)日:2020-04-28
    The present disclosure describes a vaginal system comprising segesterone acetate and ethinyl estradiol configured for thirteen 28-day product-use cycles that is compatible with male condoms comprising natural rubber latex, polyisoprene, or polyurethane and a method of providing birth control using the vaginal system wherein a secondary contraception is employed when the vaginal system is removed or expelled from the vagina for specified amounts of time during any of the product-use cycles.
    本公开描述了一种由醋酸雌二醇炔孕酮和炔雌醇组成的阴道系统,该系统配置为 13 个 28 天的产品使用周期,可与由天然橡胶乳胶、聚异戊二烯或聚氨酯组成的男用避孕套兼容;还描述了一种使用该阴道系统进行节育的方法,在任何一个产品使用周期内,当阴道系统从阴道中移出或排出特定时间时,采用二次避孕。
  • System for providing birth control
    申请人:The Population Council, Inc.
    公开号:US10940157B2
    公开(公告)日:2021-03-09
    The present disclosure relates to a vaginal system that prevents pregnancy comprised of segesterone acetate and ethinyl estradiol and is configured for thirteen 28-day product-use cycles.
    本公开涉及一种阴道避孕系统,由醋酸雌二醇炔孕酮和炔雌醇组成,产品使用周期为 13 个 28 天。
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