CAS 129453-61-8|Fulvestrant|fulvestrant|(1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol|(1S,...

基本信息

化学结构

分子式

C₃₂H₄₇F₅O₃S

分子量

606.770796

精确质量

606.31660746

电荷

InChI

InChI=1S/C32H47F5O3S/c1-30-17-15-26-25-12-11-24(38)21-23(25)20-22(29(26)27(30)13-14-28(30)39)10-7-5-3-2-4-6-8-18-41(40)19-9-16-31(33,34)32(35,36)37/h11-12,21-22,26-29,38-39H,2-10,13-20H2,1H3/t22-,26-,27+,28+,29-,30+,41?/m1/s1

InChIKey

VWUXBMIQPBEWFH-WCCTWKNTSA-N

Canonic Smiles

O=S(CCCC(C(F)(F)F)(F)F)CCCCCCCCC[C@@H]1Cc2cc(O)ccc2[C@@H]2[C@@H]1[C@@H]1CC[C@@H]([C@]1(CC2)C)O

Isomeric Smiles

S(=O)(CCCCCCCCC[C@H]1[C@H]2[C@H]3[C@](CC[C@@H]2c2c(C1)cc(O)cc2)([C@@H](O)CC3)C)CCCC(F)(F)C(F)(F)F

计算属性

JChem

Acid pKa

10.320843

质子受体

质子供体

LogD (pH = 5.5)

7.571834

LogD (pH = 7.4)

7.571323

Log P

7.571841

摩尔折射率

155.337

极化性

59.35865

极化表面积

57.53

可自由旋转的化学键

里宾斯基五规则

false

ALOGPS 2.1

Log P

6.54

LOG S

-4.96

溶解度

6.72e-03 g/l

数据来源

名称和标识

别名

FulvestrantfulvestrantICI 182,780FaslodexICI 182780ZD 9238Fulvestrant(7a,17b)-7-[9-[(4,4,5,5,5pentafluoropentyl)Sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diolZD 182780ZM 182780(7α,17β)-7-[9-[4,4,5,5,5-Pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol

商标名

Faslodex

IUPAC标准名

(1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol (1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol (1S,9R,10R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

IUPAC传统名

名称和标识

数据登录号

MDL号

CAS号

PubChem SID

PubChem CID

数据登录号

化合物性质

产品相关信息

成盐信息

Free Base

纯度

>98% (HPLC)

Empirical Formula (Hill Notation)

C32H47F5O3S

质检报告

下载链接

药理学性质

作用靶点

estrogen receptor

安全信息

保存条件

-20°C

-20°C Freezer

保存温度

2-8°C

MSDS下载

下载链接

个人保护装置

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

RTECS编号

KG7623000

德国WGK号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00947

Drug Groups

approved; investigational

Description

Fulvestrant is a drug treatment of hormone receptor-positive metastatic breast cancer in post-menopausal women with disease progression following anti-estrogen therapy. It is an estrogen receptor antagonist with no agonist effects, which works both by down-regulating and by degrading the estrogen receptor.

Indication

For the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy.

Pharmacology

Fulvestrant for intramuscular administration is an estrogen receptor antagonist without known agonist effects.

Toxicity

There is no clinical experience with overdosage in humans.

Affected Organisms

Humans and other mammals

Biotransformation

Metabolism of fulvestrant appears to involve combinations of a number of possible biotransformation pathways analogous to those of endogenous steroids, including oxidation, aromatic hydroxylation, conjugation with glucuronic acid and/or sulphate at the 2, 3 and 17 positions of the steroid nucleus, and oxidation of the side chain sulphoxide. Identified metabolites are either less active or exhibit similar activity to fulvestrant in antiestrogen models. Studies using human liver preparations and recombinant human enzymes indicate that cytochrome P-450 3A4 (CYP 3A4) is the only P-450 isoenzyme involved in the oxidation of fulvestrant; however, the relative contribution of P-450 and non-P-450 routes in vivo is unknown.

Half Life

40 days

Protein Binding

99% (mainly VLDL, LDL, and HDL)

Elimination

Fulvestrant was rapidly cleared by the hepatobiliary route with excretion primarily via the feces (approximately 90%).
Renal elimination was negligible (less than 1%).

Distribution

* 3 to 5 L/kg

References

• Kansra S, Yamagata S, Sneade L, Foster L, Ben-Jonathan N: Differential effects of estrogen receptor antagonists on pituitary lactotroph proliferation and prolactin release. Mol Cell Endocrinol. 2005 Jul 15;239(1-2):27-36. [Pubmed]

• Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. [Pubmed]

• Bross PF, Cohen MH, Williams GA, Pazdur R: FDA drug approval summaries: fulvestrant. Oncologist. 2002;7(6):477-80. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1191

Research Area: Breast cancer
Biological Activity:
Fulvestrant (Faslodex) is a synthetic estrogen receptor antagonist or selective estrogen receptor down-regulator (SERD). Unlike tamoxifen (which has partial agonist effects) and the aromatase inhibitors (which reduce the estrogen available to tumor cells), fulvestrant binds competitively to estrogen receptors in breast cancer cells, resulting in estrogen receptor deformation and decreased estrogen binding. In vitro studies indicate that fulvestrant reversibly inhibits the growth of tamoxifen-resistant, estrogen-sensitive, human breast cancer cell lines. [1] Fulvestrant is used for the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy. [2]

Sigma Aldrich

I4409

Biochem/physiol Actions
Fulvestrant (ICI 182,780) is a selective estrogen receptor down-regulator (SERD). Fulvestrant is a high affinity estrogen receptor antagonist. IC50 = 0.29 nM. Fulvestrant is the first "pure" antiestrogen with no agonistic activity both in vitro and in vivo.

TRC

F862500

A novel steroidal estrogen antagonist reported to lack any partial agonist activity. Antineoplastic (hormonal).

描述信息

参考文献

PubChem文献

数据源提供

• Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. Pubmed

• Bross PF, Cohen MH, Williams GA, Pazdur R: FDA drug approval summaries: fulvestrant. Oncologist. 2002;7(6):477-80. Pubmed

• http://en.wikipedia.org/wiki/Fulvestrant

• Wakeling, A.E., et al.: Cancer Res., 51, 3867 (1991)

• Howell, A., et al.: Br. J. Cancer, 74, 300 (1991)

• Robertson, J.F., et al.: Cancer Res., 61, 6739 (1991)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

商标名

Faslodex

IUPAC标准名

IUPAC传统名

数据登录号

MDL号

CAS号

PubChem SID

PubChem CID

化合物性质

产品相关信息

成盐信息

Free Base

纯度

>98% (HPLC)

Empirical Formula (Hill Notation)

C32H47F5O3S

质检报告

下载链接

药理学性质

作用靶点

estrogen receptor

安全信息

保存条件

-20°C

-20°C Freezer

保存温度

2-8°C

MSDS下载

下载链接

个人保护装置

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

RTECS编号

KG7623000

德国WGK号

描述信息

DrugBank

DB00947

Drug Groups

approved; investigational

Description

Indication

For the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy.

Pharmacology

Fulvestrant for intramuscular administration is an estrogen receptor antagonist without known agonist effects.

Toxicity

There is no clinical experience with overdosage in humans.

Affected Organisms

Humans and other mammals

Biotransformation

Half Life

40 days

Protein Binding

99% (mainly VLDL, LDL, and HDL)

Elimination

Fulvestrant was rapidly cleared by the hepatobiliary route with excretion primarily via the feces (approximately 90%).
Renal elimination was negligible (less than 1%).

Distribution

* 3 to 5 L/kg

References

• Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. [Pubmed]

• Bross PF, Cohen MH, Williams GA, Pazdur R: FDA drug approval summaries: fulvestrant. Oncologist. 2002;7(6):477-80. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1191

Sigma Aldrich

I4409

TRC

F862500

A novel steroidal estrogen antagonist reported to lack any partial agonist activity. Antineoplastic (hormonal).

参考文献

PubChem文献

数据源提供

• Kabos P, Borges VF: Fulvestrant: a unique antiendocrine agent for estrogen-sensitive breast cancer. Expert Opin Pharmacother. 2010 Apr;11(5):807-16. Pubmed

• Bross PF, Cohen MH, Williams GA, Pazdur R: FDA drug approval summaries: fulvestrant. Oncologist. 2002;7(6):477-80. Pubmed

• http://en.wikipedia.org/wiki/Fulvestrant

• Wakeling, A.E., et al.: Cancer Res., 51, 3867 (1991)

• Howell, A., et al.: Br. J. Cancer, 74, 300 (1991)

• Robertson, J.F., et al.: Cancer Res., 61, 6739 (1991)

生物活性

PubChem BioAssay

化合物信息

ID:823