CAS 566-48-3 MFCD00057814-Formestane 福美司坦 TAO{mole}

Formestane 福美司坦

CAS 566-48-3 MFCD00057814

化学结构图

SMILES: C[C@]12CC[C@H]3[C@@H](CCC4=C(O)C(=O)CC[C@@]43C)[C@@H]1CCC2=O

化学属性

Mol. Formula	C19H26O3
Mol. Weight	302.41
Melting Point	199-202°C
Appearance	solid
Density	1.19

别名和识别编码

Chemical Name	Formestane
CAS Number	566-48-3
Synonym	4-羟基-雄甾-4-烯-3,17-二酮 4-ANDROSTEN-4-OL-3,17-DIONE(FORMESTANE) 4-ANDROSTEN-4-OL-3,17-DIONE 4-Hydroxy-delta(sub 4)-androstenedione CGP-32349 4-Hydroxyandrost-4-ene-3,17-dione 4-HYDROXYANDROST-4-ENE-3,17-DIONE 4-hydroxy-delta(sub4)-androstenedione LENTARON 4-Hydroxy-4-androstene-3,17-dione 4-hydroxy-androst-4-ene-17-dione 福美坦福马斯坦 4-羟基雄-4-烯-3,17-二酮福美斯坦 Formestane FROMESTANE 福美司坦,4-羟基雄甾烷-4-烯-3,17-二酮芳香化酶(抗原) 4-HYDROXY-4-ANDROSTENE-3,17-DIONE 4-HYDROXYANDROSTENEDIONE 4-羟基-睾酮芳香化酶/(细胞色素P450)(P450)(抗体) 4-OHA Formesatane FORMASTANE/FORMESTANE/4-ANDROSTEN-4-OL-3,17-DIONE 4-Hydroxyandrost-4-ene-3,17-dione, 4-OHA, CGP-32349, Lentaron FORMESTANE,4-HYDROXYANDROST-4-ENE-3,17-DIONE NSC 282175 福美司坦 FORMESTANE 4-羟基雄烯二酮 FORMESTANE 98% CGP 32349 4-Hydroxyandrost-4-ene-3,17-dione CGP-32349 FORMESTAQNE B, Aromatase inhibitor 4-雄烯-4-醇-3,17-二酮 4-ANDROSTENE-4-OL-3,17-DIONE 4-羟基雄甾烷-4-烯-3,17-二酮
MDL Number	MFCD00057814
PubChem Substance ID	24894827
Chemical Name Translation	福美司坦
Wiswesser Line Notation	L E5 B666 FV OV MUTJ A1 E1 NQ
Beilstein Registry Number	1889793

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分类

{SA} A to C, Analytical Standards, Analytical/Chromatography, Antitumor Agents, Aromatase, Aromatase Inhibitors, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology, Chemical Structure, Chromatography, Drugs & Metabolites, Drugs of Abuse, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, F, Forensic and Veterinary Standards, Neat Compounds, Steroid, Tumor Growth Regulation
{SNA} A to C, Analytical Standards,
Steroids
Pharmaceuticals
Intermediates & Fine Chemicals
{Chemicalbook} 药物: 抗肿瘤药: 其它抗肿瘤药物
Inhibitors,
{SNA} A to C,

产品应用

芳香酶抑制剂,用作抗肿瘤载体,抵抗雌激素类肿瘤。

安全信息

RTECSBV8152500

WGK Germany3

GHS Symbol

Precautionary statements

P308+P313
P201 Obtain special instructions before use. 使用前获取专门指示。

Signal word Danger

Hazard statements

H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害

Hazard Codes T

Personal Protective Equipment 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

Safety Statements

S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；

Risk Statements

R60 May impair fertility 可能降低生殖能力

Storage condition 储存温度 2-8°C 2-8°C

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 250 mg/kg
SEX/DURATION            : female 3-7 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 :
   ENDOAO Endocrinology (Baltimore).  (Williams & Wilkins Co., 428 E. Preston
   St., Baltimore, MD 21203) V.1-    1917-  Volume(issue)/page/year:
   100,1684,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 120 mg/kg
SEX/DURATION            : female 11-22 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - behavioral
REFERENCE :
   ECJPAE Endocrinologia Japonica.  (Japan Pub. Trading Co., Ltd., POB 5030,
   Tokyo International, Tokyo, Japan)  V.1-    1954-  Volume(issue)/page/year:
   36,29,1989

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 136 mg/kg
SEX/DURATION            : female 2-4 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Maternal Effects - other effects
REFERENCE :
   JOENAK Journal of Endocrinology.  (Biochemical Soc. Book Depot, POB 32,
   Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1939-
   Volume(issue)/page/year: 118,93,1988

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 120 mg/kg
SEX/DURATION            : female 11-22 day(s) after conception
TOXIC EFFECTS :

其他信息

用途一:雄性激素，同化蛋白类。
用途二:芳香化酶抑制剂。用于进行性乳腺癌。
抗恶性肿瘤药:福美司坦又称福美坦、兰他隆、兰特隆，是一种抗恶性肿瘤药，主要用于治疗绝经后晚期乳腺癌，对前列腺癌也有效。福美司坦为雄烯二酮的衍生物，与氨鲁米特同属芳香酶抑制剂，为激素类抗肿瘤药。在生理情况下，它可竞争性地抑制合成酶而使组织中的雌激素的生物合成减少，继而发挥其抗癌作用。当肿瘤组织的生长须依赖雌激素的存在时，要想抑制肿瘤生长，消除雌激素介导的对肿瘤的生长刺激是必要的。本品比氨鲁米特更具选择性，活性为氨鲁米特的100～1000倍，且不抑制肾上腺皮质激素的合成，不必补给可的松等。在体外本品对芳香酶的抑制作用比氨鲁米特强60倍。本药单用不能显著降低绝经前妇女血中雌激素水平，联用戈舍瑞林(促性腺激素释放激素激动剂)对绝经前妇女雌二醇的抑制效应大于单用戈舍瑞林。福美司坦与其他芳香化酶抑制剂无交叉耐药性，无氨鲁米特的副作用。口服后胃肠道快速吸收，血药浓度达峰时间为1～1.5小时，但峰浓度个体差异较大;肌注后可存积于注射部位而缓慢吸收。表现为双相消除过程，初始消除半衰期为2～4日，终末消除半衰期为5～10日。口服后主要在肝脏代谢，以糖苷酸类代谢产物的形式从尿液中排泄。 ChemicalBook的Andy编辑整理。
MOL 文件:566-48-3.mol
上游原料:乙酸乙酯 --> 二氯甲烷 --> 碳酸钠 --> 硫酸钠 --> 氢氧化钾 --> 叔丁醇 --> 亚硫酸氢钠溶液 --> 二酮 --> 四氧化锇
用途四:芳香酶抑制剂,用作抗肿瘤载体,抵抗雌激素类肿瘤。
用途三:芳酶抑制药。
MSDS 信息:Formestane(566-48-3).msds
Sigma Aldrich:566-48-3(sigmaaldrich)
方法一:雄甾-4-烯-3，17-二酮(Ⅰ)(1.432g，5mmo1)溶于50ml叔丁醇，在室温下加入38mg(0.15mmo1)四氧化锇在2ml叔丁醇的溶液，然后加入5ml 35%双氧水，在室温下搅拌3天。加100ml盐水稀释后，用二氯甲烷(2×100m1)提取。提取液依次用100ml盐水、50ml 10%亚硫酸氢钠溶液、50ml 10%碳酸钠溶液和100ml盐水洗，无水硫酸钠干燥，浓缩。剩余物(1.824g)为化合物(Ⅱ)，溶于10ml甲醇，加入氢氧化钾(393mg，7mmo1)在3ml甲醇的溶液。加毕，在55℃搅拌10min。加入0.3ml乙酸和100ml盐水，用二氯甲烷(2×100ml)提取。期复液，合并，用100ml盐水洗，无水硫酸钠干燥，浓缩。剩余物(1.727g)经硅胶柱层析，己烷-乙酸乙酯(7：3)洗脱，得715mg福美坦，收率47%，熔点200～202℃(丙酮)。