(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 ID: 4404
• Molecular Formular: C26H33NO2
• Molecular Mass: 391.54572
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: fenretinide; N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• Synonyms: 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

Database IDs

• CAS Number: 65646-68-6
• MDL Number: MFCD00792674
• PubChem SID: 24278472; 160967836; 10388780
• PubChem CID: 5288209
• CHEMBL: 7301
• Chemspider ID: 4450416
• DrugBank ID: DB05076
• KEGG ID: D04162
• MeSH Name: Fenretinide
• Wikipedia Title: Fenretinide

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.447084
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 6.1450553
• LogD (pH = 7.4): 6.1412477
• Log P: 6.1451044
• Molar Refractivity: 128.049 cm^3
• Polarizability: 47.081615 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.31
• LOG S: -5.52
• Solubility (Water): 1.19e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: Yellow Solid
• Melting Point: 162-163°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere; -20°C, Protect from light
• RTECS: VH6420000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-61-20/21/22-36/37/38
• Safety Statements: 53-26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H315-H319-H332-H335-H360
• GHS Precautionary statements: P201-P261-P280-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%; 97%

DETAILS

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.

REFERENCES

• 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)