环氧司坦

基本信息
制备方法及用途
物化性质
毒理性
结构与计算化学

环氧司坦基本信息

中文名称：: 环氧司坦

中文别名：: 环氧司坦;
(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

英文名称：: Androst-2-ene-2-carbonitrile,4,5-epoxy-3,17-dihydroxy-4,17-dimethyl-, (4a,5a,17b)-

英文别名：: 4α,5α-epoxy-3,17β-dihydroxy-4β,17α-dimethyl-5α-androst-2-ene-2-carbonitrile;
(4|A,5|A,17|A)-4,5-Epoxy-3,17-dihydroxy-4,17-dimethylandrost-2-ene-2-carbonitrile

CAS No.：: 80471-63-2

分子式：: C₂₂H₃₁NO₃

分子量：: 357.49

精确分子量：: 357.23000

PSA：: 76.78000

InChI：: The Key: CETKWEWBSMKADK-GSXVSZIWSA-N

危险品标志：

风险术语：

安全术语：

分子结构式：

SDS：: 查看

环氧司坦制备方法及用途

制备方法

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。

合成制备方法

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。

用途简介

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。

用途

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。

环氧司坦物化性质

密度：: 1.24g/cm3
沸点：: 495ºC at 760 mmHg
闪点：: 253.2ºC
折射率：: 1.596
其它信息：: 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。

环氧司坦毒理性

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

环氧司坦分子结构与计算化学数据

分子结构数据

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

计算化学数据

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

湖北恩星生物科技有限公司

产品介绍：: 产品名称：环氧司坦 Cas号：80471-63-2 纯度：包装信息：100kg,200kg,300kg,400kg,500kg 价格：64.0元 - 100.0元

联系方式：: 联系人：邵经理电话：16621771607 手机：16621771607