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153559-49-0 分子结构
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4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid

ChemBase编号:192
分子式:C24H28O2
平均质量:348.47792
单一同位素质量:348.20893014
SMILES和InChIs

SMILES:
OC(=O)c1ccc(C(=C)c2cc3C(CCC(c3cc2C)(C)C)(C)C)cc1
Canonical SMILES:
Cc1cc2c(cc1C(=C)c1ccc(cc1)C(=O)O)C(C)(C)CCC2(C)C
InChI:
InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)
InChIKey:
NAVMQTYZDKMPEU-UHFFFAOYSA-N

引用这个纪录

CBID:192 http://www.chembase.cn/molecule-192.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
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid
IUPAC传统名
bexarotene
targretin
商标名
Targret
Targretin
Targretyn
Targrexin
Targretin-gel
别名
4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic Acid
LG 100069
LG 1069
LG 69
LGD 1069
RO 26-4455
SR 11247
Targret
Targretin
Targretyn
Targrexin
bexarotene
Bexarotene
CAS号
153559-49-0
PubChem SID
46509119
160963655
PubChem CID
82146

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 4.0707927  质子受体
质子供体 LogD (pH = 5.5) 5.4988923 
LogD (pH = 7.4) 3.8234684  Log P 6.9405375 
摩尔折射率 117.124 cm3 极化性 41.398285 Å3
极化表面积 37.3 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 6.86  LOG S -6.37 
溶解度 1.49e-04 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
Chloroform expand 查看数据来源
Methanol expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
230-231°C expand 查看数据来源
疏水性(logP)
6.9 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
作用靶点
Others 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

详细说明

详细说明

DrugBank DrugBank TRC TRC
DrugBank -  DB00307 external link
Item Information
Drug Groups approved; investigational
Description Bexarotene (Targretin) is an antineoplastic agent indicated by the FDA for Cutaneous T cell lymphoma. It has been used off-label for lung cancer, breast cancer, and Kaposi's sarcoma. [Wikipedia]
Indication Used orally for the treatment of skin manifestations of cutaneous T-cell lymphoma (CTCL) in patients who are refractory to at least one prior systemic therapy. Also used topically for the treatment of skin lesions in early (stage IA and IB) CTCL in patients who experience refractory or persistent disease with the use of other therapies or are intolerant of other therapies.
Pharmacology Bexarotene is a member of a subclass of retinoids that selectively activate retinoid X receptors (RXRs). These retinoid receptors have biologic activity distinct from that of retinoic acid receptors (RARs). Bexarotene is indicated for the treatment of cutaneous manifestations of cutaneous T-cell lymphoma in patients who are refractory to at least one prior systemic therapy. Bexarotene selectively binds and activates retinoid X receptor subtypes (RXRα, RXRβ, RXRγ). RXRs can form heterodimers with various receptor partners such as retinoic acid receptors (RARs), vitamin D receptor, thyroid receptor, and peroxisome proliferator activator receptors (PPARs). Once activated, these receptors function as transcription factors that regulate the expression of genes that control cellular differentiation and proliferation. Bexarotene inhibits the growth in vitro of some tumor cell lines of hematopoietic and squamous cell origin. It also induces tumor regression in vivo in some animal models.
Affected Organisms
Humans and other mammals
Half Life 7 hours
Protein Binding >99%
Elimination Urinary elimination of bexarotene and its known metabolites is a minor excretory pathway (<1% of administered dose).
References
Gniadecki R, Assaf C, Bagot M, Dummer R, Duvic M, Knobler R, Ranki A, Schwandt P, Whittaker S: The optimal use of bexarotene in cutaneous T-cell lymphoma. Br J Dermatol. 2007 Sep;157(3):433-40. Epub 2007 Jun 6. [Pubmed]
Dragnev KH, Petty WJ, Shah SJ, Lewis LD, Black CC, Memoli V, Nugent WC, Hermann T, Negro-Vilar A, Rigas JR, Dmitrovsky E: A proof-of-principle clinical trial of bexarotene in patients with non-small cell lung cancer. Clin Cancer Res. 2007 Mar 15;13(6):1794-800. [Pubmed]
Smit JW, Stokkel MP, Pereira AM, Romijn JA, Visser TJ: Bexarotene-induced hypothyroidism: bexarotene stimulates the peripheral metabolism of thyroid hormones. J Clin Endocrinol Metab. 2007 Jul;92(7):2496-9. Epub 2007 Apr 17. [Pubmed]
Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [Pubmed]
Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [Pubmed]
Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals -  B336750 external link
Used as an antineoplastic. A selective retinoid X receptor (RXR) agonist.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Gniadecki R, Assaf C, Bagot M, Dummer R, Duvic M, Knobler R, Ranki A, Schwandt P, Whittaker S: The optimal use of bexarotene in cutaneous T-cell lymphoma. Br J Dermatol. 2007 Sep;157(3):433-40. Epub 2007 Jun 6. Pubmed
  • Dragnev KH, Petty WJ, Shah SJ, Lewis LD, Black CC, Memoli V, Nugent WC, Hermann T, Negro-Vilar A, Rigas JR, Dmitrovsky E: A proof-of-principle clinical trial of bexarotene in patients with non-small cell lung cancer. Clin Cancer Res. 2007 Mar 15;13(6):1794-800. Pubmed
  • Smit JW, Stokkel MP, Pereira AM, Romijn JA, Visser TJ: Bexarotene-induced hypothyroidism: bexarotene stimulates the peripheral metabolism of thyroid hormones. J Clin Endocrinol Metab. 2007 Jul;92(7):2496-9. Epub 2007 Apr 17. Pubmed
  • Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. Pubmed
  • Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. Pubmed
  • Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. Pubmed
  • Boehm, M.F., et al.: J. Med. Che., 37,2930 (1994)
  • Gottardis, M.M., et al.: Cancer Res., 56, 5566 (1994)
  • Mukherjee, R., et al.: Nature, 386, 407 (1994)
  • Miller, V.A., et al.: J. Clin. Oncol., 15, 790 (1997)
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专利

专利

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