(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

• ChemBase编号: 4404
• 分子式: C26H33NO2
• 平均质量: 391.54572
• 单一同位素质量: 391.2511293
• SMILES: O=C(Nc1ccc(O)cc1)/C=C(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)\C
• Canonical SMILES: O=C(Nc1ccc(cc1)O)/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
• InChI: InChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+
• InChIKey: AKJHMTWEGVYYSE-FXILSDISSA-N

名称和登记号

名称

• IUPAC标准名: (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide; N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• IUPAC传统名: fenretinide; N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• 别名: N-(4-Hydroxyphenyl)-all-trans-retinamide; Retinoic Acid p-Hydroxyphenylamide; Ro 22-4667; all-trans-4'-Hydroxyretinanilide; all-trans-N-(4-Hydroxyphenyl)retinamide; fenretinide; N-(4-Hydroxyphenyl)All-Trans Retinamide; 4-hydroxy(phenyl)retinamide; 4-HPR; Fenretinide; 4-HYDROXYPHENYLRETINAMIDE; N-(4-Hydroxyphenyl)retinamide; Retinoic acid p-hydroxyanilide

登记号

• CAS号: 65646-68-6
• MDL号: MFCD00792674
• PubChem SID: 24278472; 160967836; 10388780
• PubChem CID: 5288209
• CHEMBL: 7301
• Chemspider ID: 4450416
• DrugBank ID: DB05076
• KEGG ID: D04162
• 医学主题词(MeSH): Fenretinide
• 维基百科标题: Fenretinide

理论计算性质

JChem

• Acid pKa: 9.447084
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 6.1450553
• LogD (pH = 7.4): 6.1412477
• Log P: 6.1451044
• 摩尔折射率: 128.049 cm^3
• 极化性: 47.081615 Å^3
• 极化表面积: 49.33 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 6.31
• LOG S: -5.52
• 溶解度: 1.19e-03 g/l

分子性质

理化性质

• 溶解度: Chloroform; Ethanol
• 外观: Yellow Solid
• 熔点: 162-163°C

安全信息

• 保存条件: Amber Vial, -20°C Freezer, Under Inert Atmosphere; -20°C, Protect from light
• RTECS编号: VH6420000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 60-61-20/21/22-36/37/38
• 安全公开号: 53-26-36/37/39-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H312-H315-H319-H332-H335-H360
• GHS警示性声明: P201-P261-P280-P305 + P351 + P338-P308 + P313
• 个人保护装置: 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
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95%; 97%

详细说明

MP Biomedicals - 02159942

Purity: 97%
Demonstrates anti-proliferative activity on human breast cancer cells in culture. Induces malignant hemopoietic cell line apoptosis.

DrugBank - DB05076

• Drug Groups: investigational
• Description: A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.
• Indication: Investigated for use/treatment in macular degeneration.
• Toxicity: "Mechanism of fenretinide (4-HPR)-induced cell death"
• References: Formelli F, Cavadini E, Luksch R, Garaventa A, Villani MG, Appierto V, Persiani S: Pharmacokinetics of oral fenretinide in neuroblastoma patients: indications for optimal dose and dosing schedule also with respect to the active metabolite 4-oxo-fenretinide. Cancer Chemother Pharmacol. 2007 Dec 8;. [Pubmed] ; Takahashi N, Watanabe Y, Maitani Y, Yamauchi T, Higashiyama K, Ohba T: p-Dodecylaminophenol derived from the synthetic retinoid, fenretinide: antitumor efficacy in vitro and in vivo against human prostate cancer and mechanism of action. Int J Cancer. 2008 Feb 1;122(3):689-98. [Pubmed] ; Simeone AM, Tari AM: How retinoids regulate breast cancer cell proliferation and apoptosis. Cell Mol Life Sci. 2004 Jun;61(12):1475-84. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - H7779

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Vitamin A acid analogue with antiproliferative activity in cultured human breast cancer cells; induces apoptosis in malignant hemopoietic cell lines.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H7779.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - F250000

A synthetic analog of Vitamin A.

参考文献

• Marth, C., et al., J. Natl. Cancer Inst. , 75 : 871, (1985).
• Grubbs, C.J., et al., Anticancer Res. , 10 : 661, (1990).
• Delia, D., et al., Cancer Res. , 53 : 6036, (1993).
• Takahashi N, Watanabe Y, Maitani Y, Yamauchi T, Higashiyama K, Ohba T: p-Dodecylaminophenol derived from the synthetic retinoid, fenretinide: antitumor efficacy in vitro and in vivo against human prostate cancer and mechanism of action. Int J Cancer. 2008 Feb 1;122(3):689-98. Pubmed
• Simeone AM, Tari AM: How retinoids regulate breast cancer cell proliferation and apoptosis. Cell Mol Life Sci. 2004 Jun;61(12):1475-84. Pubmed
• Formelli F, Cavadini E, Luksch R, Garaventa A, Villani MG, Appierto V, Persiani S: Pharmacokinetics of oral fenretinide in neuroblastoma patients: indications for optimal dose and dosing schedule also with respect to the active metabolite 4-oxo-fenretinide. Cancer Chemother Pharmacol. 2007 Dec 8;. Pubmed
• Marth, C., et al.:J. Nat. Cancer Inst., 75, 871 (1985)
• Delia, D., et al.: Cancer Res., 53, 6036 (1985)
• Costa., A., et al.: Cancer Res., 54, Suppl., 2032s (1985)
• Decensi., A., et al.: Eur. J. Cancer Prev., 3, 377 (1994)