80471-63-2

• 常用中文名：环氧司坦
• 常用英文名：Epostane
• CAS号：80471-63-2
• 分子式：C₂₂H₃₁NO₃
• 分子量：357.48600
• 相关类别： 原料药 激素及调节内分泌功能类药 垂体激素类药
• 发布时间：2018-03-15 08:00:00
• 更新时间：2024-01-27 11:27:56

• 3β-羟类固醇脱氢酶竞争抑制剂，为抗早孕药，能抑制卵巢和胎盘孕酮的合成而导致流产。用于抗早孕。

名称

• 中文名: 环氧司坦
• 英文名: 4α,5α-epoxy-3,17β-dihydroxy-4β,17α-dimethyl-5α-androst-2-ene-2-carbonitrile
• 中文别名: (4Α,5Α,17Β)-4,5-环氧-3,17-二羟基-4,17-二甲基雄甾-2-烯-2-氰; 腈波斯坦
• 英文别名: (4|A,5|A,17|A)-4,5-Epoxy-3,17-dihydroxy-4,17-dimethylandrost-2-ene-2-carbonitrile

物化性质

• 密度: 1.24g/cm3
• 沸点: 495ºC at 760 mmHg
• 熔点: 191-194°
• 分子式: C₂₂H₃₁NO₃
• 分子量: 357.48600
• 闪点: 253.2ºC
• 精确质量: 357.23000
• PSA: 76.78000
• LogP: 4.24708
• 折射率: 1.596
• 分子结构:

  1、 摩尔折射率：97.88

  2、 摩尔体积（cm³/mol）：287.3

  3、 等张比容（90.2K）：783.0

  4、 表面张力（dyne/cm）：55.1

  5、 极化率（10-24cm3）：38.80

• 计算化学:

  1.疏水参数计算参考值（XlogP）:2.7

  2.氢键供体数量:2

  3.氢键受体数量:4

  4.可旋转化学键数量:0

  5.互变异构体数量:2

  6.拓扑分子极性表面积57.4

  7.重原子数量:26

  8.表面电荷:0

  9.复杂度:782

  10.同位素原子数量:0

  11.确定原子立构中心数量:8

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.性状：从二甲基甲酰胺-水中结晶。

  2.熔点（℃）：191～194。

  3.折射率（℃,C=1,吡啶)）：67.4。

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : BV8087520 CHEMICAL NAME : Androst-2-ene-2-carbonitrile, 3,17-dihydroxy-4,17-dimethyl-4,5-epoxy-, (4-alpha,5-alpha, 17-beta)- CAS REGISTRY NUMBER : 80471-63-2 LAST UPDATED : 199503 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C22-H31-N-O3 MOLECULAR WEIGHT : 357.54 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 96 mg/kg TOXIC EFFECTS : Gastrointestinal - nausea or vomiting Reproductive - Effects on Embryo or Fetus - fetal death REFERENCE : CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 35,111,1987 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 96 mg/kg SEX/DURATION : female 7-8 week(s) after conception TOXIC EFFECTS : Reproductive - Fertility - abortion REFERENCE : CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 35,111,1987 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 84 mg/kg SEX/DURATION : female 34-41 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - abortion REFERENCE : BJOGAS British Journal of Obstetrics and Gynaecology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.82- 1975- Volume(issue)/page/year: 96,340,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 50 mg/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - abortion REFERENCE : BIREBV Biology of Reproduction. (Soc. for the Study of Reproduction, 309 W. Clark St., Champaign, IL 61820) V.1- 1969- Volume(issue)/page/year: 40,549,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 48 mg/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) REFERENCE : CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 14,437,1993 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 15 mg/kg SEX/DURATION : female 6-15 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death REFERENCE : SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 11(2),59,1991 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 10 mg/kg SEX/DURATION : female 1 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) REFERENCE : THGNBO Theriogenology. (Geron-X, Inc., P.O. Box 1108, Los Altos, CA 94022) V.1- 1974- Volume(issue)/page/year: 30,497,1988 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 2500 ug/kg SEX/DURATION : female 1 day(s) after conception TOXIC EFFECTS : Reproductive - Maternal Effects - other effects Endocrine - estrogenic REFERENCE : THGNBO Theriogenology. (Geron-X, Inc., P.O. Box 1108, Los Altos, CA 94022) V.1- 1974- Volume(issue)/page/year: 30,497,1988 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 25 mg/kg SEX/DURATION : female 5 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - other effects REFERENCE : CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 31,479,1985 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 100 mg/kg SEX/DURATION : female 5 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - menstrual cycle changes or disorders REFERENCE : CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 31,479,1985 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 175 mg/kg SEX/DURATION : female 50-54 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - abortion REFERENCE : CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 11,62,1990

制备

化合物(Ⅰ)和甲醛及苯硫酚进行硫甲基化反应，再氢化还原，在4位引入甲基，得到化合物(Ⅲ)。然后和甲酸乙酯在甲醇钠作用下缩合，在2位引入醛基，而得化合物(Ⅳ)。和羟胺成肟后，再和3位羰基环合成化合物(V)。接着用过苯甲酸过氧化在4，5-位形成环氧物(Ⅵ)，最后碱化使化合物(V)开环，得到环氧司坦。