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: 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

名称和登记号

名称

• 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

登记号

• CAS号: 153559-49-0
• PubChem SID: 46509119; 160963655
• PubChem CID: 82146

理论计算性质

JChem

• Acid pKa: 4.0707927
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 5.4988923
• LogD (pH = 7.4): 3.8234684
• Log P: 6.9405375
• 摩尔折射率: 117.124 cm^3
• 极化性: 41.398285 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 6.86
• LOG S: -6.37
• 溶解度: 1.49e-04 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 230-231°C
• 疏水性(logP): 6.9

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 作用靶点: Others

产品相关信息

• 成盐信息: Free Base

详细说明

DrugBank - DB00307

• 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 (RXR_α, RXR_β, RXR_γ). 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

Used as an antineoplastic. A selective retinoid X receptor (RXR) agonist.

参考文献

• 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
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