米非司酮_MSDS_用途_密度_米非司酮CAS号【84371-65-3】

Mifepristone是黄体酮受体 (PR) 和糖皮质激素受体 (GR) 拮抗剂,体外实验中的 IC50 值分别为0.2 nM 和2.6 nM。

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[ 描述 ]:

Mifepristone是黄体酮受体 (PR) 和糖皮质激素受体 (GR) 拮抗剂,体外实验中的 IC50 值分别为0.2 nM 和2.6 nM。

[ 相关类别 ]:

信号通路 >> 自噬 >> 自噬

信号通路 >> G 蛋白偶联受体/G 蛋白 >> 糖皮质激素受体

信号通路 >> 其他 >> 孕激素受体

研究领域 >> 内分泌

[ 靶点 ]

IC50: 0.2 nM (progesterone receptor, in T47D cells), 2.6 nM (glucocorticoid receptor, in A549 cells)[1]

[体外研究]

第一种竞争性黄体酮拮抗剂米非司酮的发现刺激了对更有效和更具选择性的抗孕激素的强烈追求[1]。在10μM暴露于米非司酮4天后评估细胞生长,浓度接近人类可达到的血浆浓度。当与米非司酮联合给予HeLa细胞时,顺铂的抗增殖作用增强。在HeLa细胞中,顺铂与米非司酮组合的IC50比单独顺铂(34.2μM)低(14.2μM),差异大约为2.5倍。用米非司酮治疗后,细胞内顺铂在HeLa细胞中的积累量增加了2倍,显着差异(p = 0.009),与单独的顺铂相比,从0.79到1.52μg/ mg蛋白质[2]。

[体内研究]

宫颈肿瘤异种移植模型仅用顺铂治疗,与对照组相比存在肿瘤生长抑制。然而,在所用剂量下,顺铂和米非司酮联合使用时肿瘤体重减轻更为显着(p <0.05),与研究结束时单独治疗相比,减少了约50％[2]。对成年雄性Sprague-Dawley大鼠进行4天狂欢样EtOH给药方案(每8小时3至5g/kg/ig,设计产生<300mg/dL的峰值血液EtOH水平(BELs))。动物亚组接受皮下注射米非司酮(花生油中20或40 mg/kg)。尽管米非司酮对未经过EtOH治疗的动物的行为没有显着改变,但米非司酮(40 mg/kg)的预处理显着降低了EtOH戒断的严重程度。饮食和药物之间的显着相互作用,F(5,55)= 3.92,p <0.05,使得接受载体的EtOH处理的动物或20mg/kg米非司酮显示出比接受该物质的未接受EtOH的动物显着更多的EtOH戒断迹象。药物治疗。重要的是,用40 mg/kg米非司酮治疗可以剂量依赖的方式显着降低EtOH戒断的严重程度[3]。

[激酶实验]

将T47D人乳腺癌细胞以每孔10,000个细胞接种于96孔组织培养板中的测定培养基[不含酚红的RPMI培养基含有5％（v / v）活性炭处理的FBS和1％（v / v）青霉素 - 链霉素。两天后，倾析培养基并在新鲜测定培养基中以0.1％（v / v）二甲基亚砜的终浓度加入米非司酮或对照。二十四小时后，使用SEAP试剂盒进行碱性磷酸酶测定。简而言之，倾析培养基并将细胞在室温下用5％（v / v）福尔马林固定30分钟。在室温下用Hanks缓冲盐水溶液洗涤细胞一次。然后加入等体积（0.05mL）的1x稀释缓冲液，测定缓冲液和1:20底物/增强剂混合物。在室温下在黑暗中孵育1小时后，将裂解物转移至白色96孔板中，并使用LuminoSkan Ascent [1]读取发光。

[细胞实验]

使用HeLa和CaSki人宫颈癌细胞系。使用XTT测定评估米非司酮对暴露于顺铂的细胞增殖的影响。该测定基于黄色四唑盐XTT的裂解，通过代谢活性细胞形成橙色甲dye染料。程序如下。将细胞接种到96孔板中;在100μL培养基中，每孔密度为6×103个活细胞。在单独使用顺铂或顺铂加米非司酮联合治疗结束时，每孔加入50μLXTT（终浓度0.3 mg / mL），然后在37°含5％CO2的潮湿气氛中孵育4小时。 C。使用微量滴定板ELISA读数器[2]在492nm处通过分光光度法测量样品的吸光度。

[动物实验]

小鼠[2]在6-8周龄的雌性裸鼠皮下植入6×106个HeLa细胞的侧腹。一旦肿瘤为~5×5mm，将动物配对进入治疗组和对照组。每组由8只荷瘤小鼠组成。腹膜内给药药物或载体在第0天开始。顺铂作为单一药剂，在第1天至第3天每天以3mg / kg的剂量腹膜内给药;作为单一药剂的米非司酮的剂量为2mg / kg /天，皮下注射3天;在组合研究中，小鼠以相同的时间表同时接受顺铂，并且在顺铂给药前3天以相同的剂量接受米非司酮。对照动物仅接受载体。给药后，称重小鼠，每周两次用卡尺测量肿瘤。计算肿瘤重量。实验进行了74天，之后将所有动物称重并人道地安乐死。大鼠[3]使用成年雄性Sprague-Dawley大鼠，在到达时体重为224-245g。在0800施用EtOH或对照饮食后，每天一次皮下（sc）施用米非司酮（20或40mg / kg）或媒介物（花生油）。将米非司酮悬浮在花生油中并在注射前至少24小时超声处理30分钟，然后将其储存在4℃直至需要。在给药之前和根据需要将悬浮液涡旋10至15分钟。

[参考文献]

[1]. Jiang W, et al. New progesterone receptor antagonists: phosphorus-containing 11beta-aryl-substituted steroids. Bioorg Med Chem. 2006 Oct 1;14(19):6726-32.

[2]. Jurado R, et al. Cisplatin cytotoxicity is increased by mifepristone in cervical carcinoma: an in vitro and in vivo study. Oncol Rep. 2009 Nov;22(5):1237-45.

[3]. Sharrett-Field L, et al. Mifepristone Pretreatment Reduces Ethanol Withdrawal Severity In Vivo. Alcohol Clin Exp Res. 2013 Aug;37(8):1417-23.

[相关活性小分子]

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
628.6±55.0 °C at 760 mmHg

[ 熔点 ]:
195-198°C

[ 分子式 ]:
C₂₉H₃₅NO₂

[ 分子量 ]:
429.594

[ 闪点 ]:
334.0±31.5 °C

[ 精确质量 ]:
429.266785

[ PSA ]:
40.54000

[ LogP ]:
4.95

[ 外观性状 ]:
淡黄色固体

[ 蒸汽压 ]:
0.0±1.9 mmHg at 25°C

[ 折射率 ]:
1.623

[ 储存条件 ]:
2-8°C

[ 水溶解性 ]:
可溶于：氯仿

详细MSDS(安全技术说明书)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KG2955000

CHEMICAL NAME :: Estra-4,9-dien-3-one, 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propyny l)-, (11-beta, 17-beta)-

CAS REGISTRY NUMBER :: 84371-65-3

LAST UPDATED :: 199709

DATA ITEMS CITED :: 26

MOLECULAR FORMULA :: C29-H35-N-O2

MOLECULAR WEIGHT :: 429.65

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 mg/kg

SEX/DURATION :: female 7 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 56,32,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 14 mg/kg

SEX/DURATION :: female 7-8 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 35,307,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 mg/kg

SEX/DURATION :: female 6 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: EOGRAL European Journal of Obstetrics, Gynecology and Reproductive Biology. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.3- 1973- Volume(issue)/page/year: 28,249,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: OBGNAS Obstetrics and Gynecology. (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.1- 1953- Volume(issue)/page/year: 74,653,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 mg/kg

SEX/DURATION :: female 6 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - abortion

REFERENCE :: GOBIDS Gynecologic and Obstetric Investigation. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.9- 1978- Volume(issue)/page/year: 29,13,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 mg/kg

SEX/DURATION :: female 6-8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

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 :: Oral

DOSE :: 160 mg/kg

SEX/DURATION :: female 1-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: BMEMDK Biological Memoirs. (International Publishers, C 131, Mahanagar, Lucknow 226 006, India) V.1- 1976- Volume(issue)/page/year: 15,107,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 mg/kg

SEX/DURATION :: female 7-9 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 :: SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 15,47,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6250 ug/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - abortion

REFERENCE :: SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 14,332,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 50 mg/kg

SEX/DURATION :: female 21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 79,1,1987

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 - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 80,487,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 10 mg/kg

SEX/DURATION :: female 1-2 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 80,487,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 45 mg/kg

SEX/DURATION :: female 5-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 83,73,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 30 mg/kg

SEX/DURATION :: female 2 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) Reproductive - Maternal Effects - other effects

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 83,279,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 mg/kg

SEX/DURATION :: female 1-2 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) Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) Reproductive - Effects on Embryo or Fetus - other effects to embryo

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 41,551,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 mg/kg

SEX/DURATION :: female 6-8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

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 :: Oral

DOSE :: 3 mg/kg

SEX/DURATION :: female 7-9 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 :: SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 15,47,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 4 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 :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 36,549,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2 mg/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 96,299,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2 mg/kg

SEX/DURATION :: female 7 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 :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 47,317,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 ug/kg

SEX/DURATION :: female 7 day(s) after conception

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: 47,317,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 22500 ug/kg

SEX/DURATION :: female 32-36 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Endocrine - changes in luteinizing hormone Reproductive - Fertility - abortion

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 88,99,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 70 mg/kg

SEX/DURATION :: female 32-39 day(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: 41,85,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 10 mg/kg

SEX/DURATION :: female 15-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: JMPMAO Journal of Medical Primatology. (Munksgaard International Publishers, 238 Main St., Cambridge, MA 02142) V.1- 1972- Volume(issue)/page/year: 23,319,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 8 mg/kg

SEX/DURATION :: female 21 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition Endocrine - effect on menstrual cycle

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 97,233,1993 *** REVIEWS *** TOXICOLOGY REVIEW HUREEE Human Reproduction. (IRL Press Inc., POB Q, McLean, VA 22101) V.1- 1986- Volume(issue)/page/year: 1,107,1986

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[ 符号 ]:

GHS08

[ 信号词 ]:
Danger

[ 危害声明 ]:
H360

[ 警示性声明 ]:
P201-P280-P308 + P313

[ 个人防护装备 ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
T: Toxic;

[ 风险声明 (欧洲) ]:
R60

[ 安全声明 (欧洲) ]:
S53-S22-S36/37/39-S45

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
KG2955000

米非司酮上游产品

米非司酮下游产品

方法1：以4，9雌甾二烯-3，17-二酮的3位缩酮化合物(Ⅰ)为原料，和丙炔溴化镁格氏试剂反应，在17位引入丙炔基，得到化合物(Ⅱ)。接着对5位烯键进行选择性环氧化，得化合物(Ⅲ)。然后在含溴化铜-甲硫醚络合物的四氢呋喃中，和对二甲氨基苯溴化镁反应，在11位引入对二甲氨基苯基，得化合物(Ⅳ)。最后在甲醇中，用盐酸水解并脱水，得到米非司酮。收率21.5%。

方法2：同样以4，9-雌甾二烯-3，17-二酮为原料，对3位羰基进行保护；然后先环氧化，再在17位引入丙炔基，在11位引入对二甲氨基苯基，最后水解得到米非司酮。和路线1相比，仅在环氧化和引入丙炔基的先后顺序上不同，反应步骤相同。总收率35%-40%。

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