乙基雌烯醇 | 965-90-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 乙基雌烯醇
• 中文别名: 乙雌烯醇
• 英文名称: ethylestrenol
• 英文别名: 17α-ethyl-estr-4-en-17β-ol；19-nor-17βH-pregn-4-en-17-ol；(8R,9S,10R,13S,14S,17S)-17-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 965-90-2
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: AOXRBFRFYPMWLR-XGXHKTLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

乙炔雌醇与大鼠肝脏的线粒体后上清液以及辅助因子一起孵化，主要代谢物为诺炔雄酮。第二种（次要）代谢物暂时被鉴定为17 alpha-乙基-5 epsilon-雌烷-3 epsilon,17 beta-二醇。提出了乙炔雌醇在大鼠中的代谢途径。

Ethylestrenol incubated with a post-mitochondrial supernatant fraction of rat liver plus co-factors gives norethandrolone as the major metabolite. A second (minor) metabolite was tentatively identified as 17 alpha-ethyl-5 epsilon-estrane-3 epsilon,17 beta-diol. A pathway is suggested for the metabolism of ethylestrenol in the rat.

来源:Hazardous Substances Data Bank (HSDB)

代谢

奥拉布林在C-3位置被氧化形成了尼勒瓦，尼勒瓦在人體內經過環化還原和側鏈羟基化轉化為19-諾孕三醇。識別這種代謝物，並在尿液中檢測，是用於懷疑使用禁藥的運動員的測試。

Orabolin was oxidized at C-3 to form nilevar which in turn was metabolized in man by a ring reduction and side chain hydroxylation to form a 19-norpregnatriol. Identification of this metabolite, detection in urine is test for athletes suspected of drug misuse.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

醋酸乙炔雌醇对雌性大鼠具有抗急性盐酸可卡因毒性的保护作用。肝脏酶诱导可能产生许多类固醇的保护性抗毒活性，而与其经典的激素性质无关。

Catatoxic steroid ethylestrenol protected female rats against acute cocaine-HCl toxicity. Hepatic enzyme induction may produce protective catatoxic activity of many steroids, irrespective of their classical hormone properties

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

香豆素类或茚满二酮衍生物的抗凝作用，或非甾体抗炎镇痛药、水杨酸衍生物在治疗剂量下，与同服雄激素类固醇（尤其是17-α-烷基化化合物）时可能会增加，这是由于雄激素类固醇通过改变凝血因子的合成或分解，降低了促凝血因子的浓度，并增加了抗凝剂受体的亲和力；在与雄激素类固醇同时使用期间和之后，可能需要根据凝血酶原时间测定来调整抗凝剂的剂量。/雄激素类固醇/

Anticoagulant effects of coumarin- or indandione-derivative or anti-inflammatory analgesics, nonsteroidal or salicylates, in therapeutic doses may be increased during concurrent use with anabolic steroids, especially 17-alpha-alkylated compounds, because of decreased procoagulant factor concentration caused by alteration of procoagulant factor synthesis or catabolism and increased receptor affinity for the anticoagulant; anticoagulant dosage adjustment based on prothrombin time determinations may be required during and following concurrent use with anabolic steroids. /Anabolic Steroids/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

糖皮质激素和促皮质激素分泌的抑制，可能导致肾上腺功能不足。在停止使用糖皮质激素后，那些长期使用大剂量的患者可能会出现头昏、恶心、无力或抑郁症状。

Concurrent use of antidiabetic agents, sulfonylurea or insulin with anabolic steroids may decrease blood glucose concentration; diabetic patients should be closely monitored for signs of hypoglycemia ... /Anabolic Steroids/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

皮质类固醇、糖皮质激素（尤其是具有显著盐皮质激素活性的），长期治疗用的促肾上腺皮质激素或含钠药物或食物与同化类固醇的并用可能增加水肿的可能性；此外，糖皮质激素或促肾上腺皮质激素与同化类固醇的并用可能促进严重痤疮的发展。/同化类固醇/

Concurrent use of corticosteroids, glucocorticoid, especially with significant mineralocorticoid activity, prolonged therapeutic corticotropin or sodium-containing medications or foods with anabolic steroids may increase the possibility of edema; in addition, concurrent use of glucocorticoids or corticotropin with anabolic steroids may promote development of severe acne. /Anabolic Steroids/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要进行治疗……。监测休克，如有必要进行治疗……。预见并治疗癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

[3H]乙炔雌醇在大鼠体内的吸收、分布、代谢和排泄进行了研究。2. 大约三分之一的口服剂量被吸收；在10天内，剂量的17%通过尿液排出，83%通过粪便排出。3. 剂量在大鼠体内广泛分布，发现肾脏和肝脏分别含有其他所有组织的平均特异性活性的2.5-3倍和5-7倍。4. 尿液中仅检测到未改变的乙炔雌醇。粪便中也发现了乙炔雌醇，同时还发现了两种不同的二羟基化的二氢衍生物和一种三羟基化的二氢衍生物。

The absorption, distribution, metabolism and excretion of [3H]ethylestrenol were studied in the rat. 2. Approximately one third of an intragastric dose was absorbed; 17% of the dose was excreted in urine and 83% in faeces within 10 days. 3. The dose is distributed throughout the rat, and kidney and liver were found to contain respectively 2.5-3 and 5-7 times the average specific activity of all other tissues. 4. Unchanged ethylestrenol was the only component detected in urine. Ethylestrenol was also found in faeces, along with two different dihydroxylated dihydro derivatives and one trihydroxylated dihydro derivative.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

尚不清楚合成代谢类固醇是否分布到母乳中。/合成代谢类固醇/

It is not known whether anabolic steroids are distributed into breast milk. /Anabolic Steroids/

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  乙基雌烯醇 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (5R,8R,9R,10S,13S,14S,17S)-17-ethyl-13-methyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  通过13 C-NMR光谱对17α-乙基雌二醇17β-醇（合成代谢类固醇乙基雌烯醇中的杂质）中C-5处的构型进行赋值。

  摘要：

  通过13 C-NMR光谱确定了在C-5的17α-乙基雌二醇17β-醇中的立体化学，发现它是乙基烯醇中的杂质。连接至C-5的氢原子为α-构型。通过部分氘化，非共振13C-（1H）-解偶联以及与模型化合物的比较来确认共振分配。

  DOI：

  10.1002/jps.2600670849
• 作为产物：
  描述：

  雌甾-4-烯-17-醇 在 chromium(VI) oxide 、 硫酸 、 丙酮 作用下， 生成 乙基雌烯醇
  参考文献：
  名称：

  de Winter et al., Chemistry and industry, 1959, p. 905

  摘要：

  DOI：

文献信息

• [EN] PEPTIDE-BASED MULTIPLE-DRUG DELIVERY VEHICLE<br/>[FR] VÉHICULE D'ADMINISTRATION DE MÉDICAMENTS MULTIPLES À BASE DE PEPTIDES
  申请人：ARIEL-UNIVERSITY RES AND DEV COMPANY LTD

  公开号：WO2017068577A1

  公开（公告）日：2017-04-27

  A molecular structure comprising a targeting moiety, a multi-functional peptide platform and a plurality of controllably released bioactive agents attached thereto is provided herein.

  本文提供了一种包括靶向基团、多功能肽平台和附着在其上的多种可控释放的生物活性剂的分子结构。
• [EN] BIOREVERSABLE PROMOIETIES FOR NITROGEN-CONTAINING AND HYDROXYL-CONTAINING DRUGS<br/>[FR] PRO-FRAGMENTS BIORÉVERSIBLES POUR MÉDICAMENTS CONTENANT DE L'AZOTE ET DE L'HYDROXYLE
  申请人：BAIKANG SUZHOU CO LTD

  公开号：WO2015081891A1

  公开（公告）日：2015-06-11

  Disclosed are promoieties of the following formula which can be used to form prodrugs of nitrogen-containing or hydroxyl-containing drug or a pharmaceutically active agent: (I) and pharmaceutical compositions comprising the prodrugs.

  披露了以下公式的促销性质，它们可用于形成含有氮或羟基的药物或药物活性剂的的前药：(I)以及包含这些前药的药物组合物。
• [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE<br/>[FR] AGONISTES DE RÉCEPTEUR 5-HT2C ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：ARENA PHARM INC

  公开号：WO2017023679A1

  公开（公告）日：2017-02-09

  Provided in some embodiments are compounds of Formula A, as defined herein, that modulate the activity of 5-HT2C receptor. Also provided in some embodiments are methods, such as, for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea.

  在某些实施例中提供了一些符合本文所定义的A式化合物，其调节5-HT2C受体的活性。在某些实施例中还提供了一些方法，例如用于体重管理、诱导饱腹感、减少食物摄入，以及预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病理性赌博、奖赏缺乏综合征和性成瘾，强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲症），睡眠障碍（包括失眠、睡眠结构碎裂和慢波睡眠紊乱），尿失禁，精神障碍（包括精神分裂症、厌食症和暴食症），阿尔茨海默病，性功能障碍，勃起功能障碍，癫痫，运动障碍（包括帕金森病和抗精神病药物引起的运动障碍），高血压，血脂异常，非酒精性脂肪肝病，肥胖相关肾脏疾病和睡眠呼吸暂停症。
• [EN] THERANOSTIC CONJUGATES<br/>[FR] CONJUGUÉS THÉRANOSTIQUES
  申请人：ARIEL SCIENT INNOVATIONS LTD

  公开号：WO2021009759A1

  公开（公告）日：2021-01-21

  Provided herein is a drug delivery (DD) system for ratiometric luminescence determination of drug release degree in drug delivery monitoring, which includes a drug, a switchable reporter and non-switchable reporter providing two distinguishable signals for detection; or a single switchable reporter providing two distinguishable signals for detection, and a cleavable linker connecting a drug to a switchable reporter, as well as a method for ratiometric luminescence determination of drug release in a target in vivo or in vitro), which is effected by administering the DD system provided herein that is capable of releasing a drug from the DD system, measuring two luminescent signals provided by the switchable reporter and the non-switchable reporter, or the single switchable reporter, determining the ratio between these two luminescence signals, and determining the drug release degree through the ratio between the two luminescence signals.

  本文提供了一种药物递送（DD）系统，用于药物递送监测中药物释放程度的比例荧光测定，该系统包括一种药物、一种可切换的报告物和一种不可切换的报告物，用于提供两种可区分的信号以进行检测；或者一种单一可切换的报告物，用于提供两种可区分的信号以进行检测，以及一种可切割的连接剂，连接药物和可切换的报告物，以及一种比例荧光测定方法，用于在目标（体内或体外）中测定药物释放，通过给予本文提供的能够从DD系统中释放药物的DD系统，测量可切换的报告物和不可切换的报告物提供的两个发光信号，或者单一可切换的报告物，确定这两个发光信号之间的比例，并通过这两个发光信号之间的比例确定药物释放程度。
• METHODS AND SYSTEMS FOR DESIGNING AND/OR CHARACTERIZING SOLUBLE LIPIDATED LIGAND AGENTS
  申请人：TUFTS MEDICAL CENTER

  公开号：US20160052982A1

  公开（公告）日：2016-02-25

  The present application provides methods for preparing soluble lipidated ligand agents comprising a ligand entity and a lipid entity, and in some embodiments, provides relevant parameters of each of these components, thereby enabling appropriate selection of components to assemble active agents for any given target of interest.

  本申请提供了制备可溶性脂质化配体药剂的方法，包括配体实体和脂质实体，并在某些实施例中提供了这些组分的相关参数，从而使得能够适当选择组分来组装出针对任何感兴趣的靶点的活性药剂。