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90357-06-5 分子结构
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N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide

ChemBase编号:999
分子式:C18H14F4N2O4S
平均质量:430.3733728
单一同位素质量:430.06104082
SMILES和InChIs

SMILES:
S(=O)(=O)(CC(O)(C)C(=O)Nc1cc(c(cc1)C#N)C(F)(F)F)c1ccc(F)cc1
Canonical SMILES:
N#Cc1ccc(cc1C(F)(F)F)NC(=O)C(CS(=O)(=O)c1ccc(cc1)F)(O)C
InChI:
InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
InChIKey:
LKJPYSCBVHEWIU-UHFFFAOYSA-N

引用这个纪录

CBID:999 http://www.chembase.cn/molecule-999.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
(2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
IUPAC传统名
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
bicalutamide
(2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
商标名
Casodex
别名
Bicalutamide
N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
Bicalutamide (CDX)
2-(1,2-Diphenylethoxy)-N,N,N-(trimethyl-d9)ethanaminium Bromide
[2-(1,2-Diphenylethoxy)ethyltrimethyl-d9]ammonium Bromide
ES 132-d9
Lysbex-d9
Lysibex-d9
Lysobex-d9
Medipectol-d9
OM-Tussic-d9
OM-Tussis-d9
Rea-tos-d9
Sedobex-d9
Thoragol-d9
Bibenzonium-d9 Bromide
Bicalutamide
(2r)-N-[4-Cyano-3-(Trifluoromethyl)Phenyl]-3-[(4-Fluorophenyl)Sulfonyl]-2-Hydroxy-2-Methylpropanamide
Casodex
Cosudex
Calutide
Kalumid
Bicalutamide(Casodex)
CAS号
90357-06-5
MDL号
MFCD00869971
PubChem SID
46505386
160964462
46506892
PubChem CID
56069
2375

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 11.947144  质子受体
质子供体 LogD (pH = 5.5) 2.7092955 
LogD (pH = 7.4) 2.7092834  Log P 2.7092955 
摩尔折射率 96.5895 cm3 极化性 36.135174 Å3
极化表面积 107.26 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.7  LOG S -4.67 
溶解度 9.28e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
5 mg/L expand 查看数据来源
DMSO expand 查看数据来源
DMSO: >5 mg/mL expand 查看数据来源
H2O: insoluble expand 查看数据来源
外观
powder expand 查看数据来源
疏水性(logP)
2.5 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
desiccated expand 查看数据来源
protect from light expand 查看数据来源
RTECS编号
TX1413500 expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
36/37/38 expand 查看数据来源
安全公开号
26 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
作用靶点
androgen receptor expand 查看数据来源
生物活性机理
Antiandrogen expand 查看数据来源
Prevent the action of androgens by blocking the receptors for androgens on the cells of tissues, for example, the cells of the prostate gland expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Antiandrogen investigated for the treatment of advanced prostate cancer expand 查看数据来源
Empirical Formula (Hill Notation)
C18H14F4N2O4S expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB02932 external link
Drug information: experimental
DrugBank -  DB01128 external link
Item Information
Drug Groups approved
Description Bicalutamide is an oral non-steroidal anti-androgen for prostate cancer. It binds to the androgen receptor.
Indication For treatment (together with surgery or LHRH analogue) of advanced prostatic cancer.
Pharmacology Bicalutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Bicalutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Bicalutamide blocks the action of androgens of adrenal and testicular origin which stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration.
Affected Organisms
Humans and other mammals
Biotransformation Bicalutamide undergoes stereo specific metabolism. The S (inactive) isomer is metabolized primarily by glucuronidation. The R (active) isomer also undergoes glucuronidation but is predominantly oxidized to an inactive metabolite followed by glucuronidation.
Absorption Bicalutamide is well-absorbed following oral administration, although the absolute bioavailability is unknown.
Half Life 5.9 days
Protein Binding 96%
Clearance * Apparent oral cl=0.32 L/h [Normal Males]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1190 external link
Research Area
Description Endocrinology
Biological Activity
Description Bicalutamide (Casodex, Cosudex, Calutide, Kalumid) is an androgen receptor (AR) antagonist with IC50 of 0.16 μM.
Targets AR
IC50 0.16 μM [1]
In Vitro Bicalutamide undergoes an antagonist-to-agonist switch, stimulating AR activity. Bicalutamide treatment of LNCaP/AR(cs) cells in absence of the synthetic androgen R1881 results in altered gene expression consistent with its well-documented agonist activity in context of AR overexpression. Bicalutamide induces cell proliferation in a dose-dependent manner, and only partially antagonized the effects of R1881. Bicalutamide treatment also results in a significant amount of nuclear AR, although less than that observed with R1881. Bicalutamide exhibits partial agonist activity as evidenced by induction of DNA binding at AR target genes and incomplete antagonism of the effects of R1881. In absence of R1881, Bicalutamide partially activates VP16-AR–mediated transcription, indicative of AR binding to DNA. In LNCaP/AR-luc cells with a stably integrates AR-driven luciferase reporter construct. In the presence of R1881, Bicalutamide shows only weak partial antagonism of VP16-AR–mediated transcription with an IC50 of 0.35 μM. [1] Micromolar bicalutamide causes a significant dose-dependent reduction in clonogenicity. [2] Dual inhibition of the AR and mTOR signaling pathways provides further benefit with the ridaforolimus-bicalutamide combination producing syner -gistic antiproliferative effects in prostate cancer cells in vitro when compared with each agent alone. [3]
In Vivo Single bicalutamide reduces tumor growth by 79%, at defined submaximal doses. The ridaforolimus-bicalutamide combination exhibits improved and potent antitumor activity, almost completely abrogating tumor growth. The combination is also well tolerated, as evidenced by no significant changes in body weight over the course of treatment. Plasma PSA levels are again tightly linked to tumor growth in the combination-treated mice. [3]
Clinical Trials Bicalutamide plus MDV3100 has entered in a phase II clinical trial in the treatment of prostatic neoplasms.
Features
Combination Therapy
Description Single Bicalutamide reduces tumor growth by 79%, at defined submaximal doses. The ridaforolimus-bicalutamide combination exhibits improved and potent antitumor activity, almost completely abrogating tumor growth. The combination is also well tolerated, as evidenced by no significant changes in body weight over the course of treatment. Plasma PSA levels are again tightly linked to tumor growth in the combination-treated mice. [3] Bicalutamide plus MDV3100 has entered in a phase II clinical trial in the treatment of prostatic neoplasms.
Protocol
Kinase Assay [1]
Whole-cell competitive binding assays Whole-cell competitive binding assays are performed in LNCaP/AR(codon-switch) (LNCaP/AR(cs)) (harbors a mixture of exogenous wild-type AR and endogenous mutant AR (T877A)) and cells propagated in Iscove’s or RPMI media supplemented with 10% fetal bovine serum, or during the assay with 10% charcoal-stripped, dextran-treated fetal bovine serum (CSS). Cells are pre-incubated with 18F-FDHT, increasing concentrations (1pM to 1μM) of cold Bicalutamide are added, and the assay is performed to measure specific uptake of 18F-FDHT (4). IC50 values are determined using a one site binding model with least squares curve fitting and R2 > 0.99.
Cell Assay [3]
Cell Lines C4-2 cell
Concentrations 0-1 μM
Incubation Time 72 hours
Methods Exponentially growing C4-2 cells are plated into two 96-well plates and incubated overnight at 37 ?C. Twenty-four hours later one plate is aspirated and stored at -80 ?C and the other treated with 10-fold serial concentrations of ridaforolimus (1000 nM to 0.0001 nM) or vehicle (ethanol). Following 72 hours culture at 37 ?C, the plates are assessed simultaneously for cell growth using the Cy qUANT Cell Proliferation Assay kit. Bicalutamide and Ridaforolimus combination proliferation assays are performed similarly except cell growth is determined as the change in cell number between vehicle control and compound treated cells after 72 hours in culture.
Animal Study [3]
Animal Models Male nude mice bearing C4-2 cells
Formulation 4% ethanol, 5% Tween 80, and 5% propylene glycol
Doses 10 mg/kg
Administration Administered via p.o.
References
[1] Clegg NJ, et al. Cancer Res. 2012, 72(6), 1494-1503.
[2] Colquhoun AJ, et al. Prostate Cancer Prostatic Dis. 2012.
[3] Squillace RM, et al. Int J Oncol. 2012.
Sigma Aldrich -  B9061 external link
Biochem/physiol Actions
Bicalutamide (CDX) is a non-steriodal Androgen Receptor (AR) antagonist and a pure antiandrogen. It acts via balancing histone acetylation/deacetylation and recruitment of coregulators. Bicalutamide (CDX) abolishes androgen-mediated expression. For example, MMP13 upregulation in prostate cancer, PLZF (promyelocytic leukemia zinc finger protein), and GADD45γ (growth arrest and DNA damage inducible, gamma). Bicalutamide (CDX) is inhibited by non-genomic, transcription-independent stimulation of PI3K/AKT phosphorylation by androgens.
Toronto Research Chemicals -  B373502 external link
Labelled Bibenzonium bromide (B373500). Used for preparation of substituted indoles as cysteinyl leukotriene receptor modulators.

参考文献

参考文献

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