Fenretinide

CAS No:
65646-68-6 Category:
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Product Details:

  • CAS No: 65646-68-6
  • AHFC code:
  • Synonyms: 4-HPR 4-hydroxy(phenyl)retinamide N-(4-Hydroxyphenyl)All-Trans Retinamide
  • ATC Code:
  • Chemical Formula: C9H11FN2O5
  • Molecular Weight: 391.5457
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB05076 (DB03922)
  • SMILES: CC(C=CC1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(=O)NC1=CC=C(O)C=C1
  • InChl: AKJHMTWEGVYYSE-FXILSDISSA-N
  • PubChem: 5288209
  • IUPAC: (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

Additional Details

Indication:
Investigated for use/treatment in macular degeneration.
Pharmacodynamics:
Mode of Action:
Fenretinide inhibits the growth of several human cancer cell lines, acting through both retinoid-receptor-dependent and retinoid-receptor-independent mechanisms.1In vivo, fenretinide selectively accumulates in breast tissue and is particularly active in inhibiting rat mammary carcinogenesis.1 An important feature of fenretinide is its ability to inhibit cell growth through the induction of apoptosis rather than through differentiation, an effect that is strikingly different from that of vitamin A.1 In contrast to tamoxifen, which inhibits only estrogen receptor (ER)-positive tumors, fenretinide induces apoptosis in both ER-positive and ER-negative breast cancer cell lines.2 All of these properties render fenretinide an attractive candidate for breast cancer chemoprevention.
Metabolism:
Toxicity:
"Mechanism of fenretinide (4-HPR)-induced cell death"
General Reference:
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
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