Fenretinide

Last updated
Fenretinide
Fenretinide.svg
Fenretinide 3D spacefill.png
Names
Preferred 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
Other names
N-(4-Hydroxyphenyl)retinamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.164.069 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH Fenretinide
PubChem CID
UNII
  • 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+ Yes check.svgY
    Key: AKJHMTWEGVYYSE-FXILSDISSA-N Yes check.svgY
  • InChI=1/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+
    Key: AKJHMTWEGVYYSE-FXILSDISBU
  • O=C(Nc1ccc(O)cc1)\C=C(\C=C\C=C(\C=C\C2=C(\CCCC2(C)C)C)C)C
Properties
C26H33NO2
Molar mass 391.546 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Fenretinide (N-(4-hydroxyphenyl)retinamide; 4-HPR) (INN) is a synthetic retinoid derivative. Retinoids are substances related to vitamin A. It has been investigated for potential use in the treatment of cancer, as well as in the treatment of cystic fibrosis, [1] rheumatoid arthritis, acne, psoriasis, and has been found to also slow the production and accumulation of a toxin that leads to vision loss in Stargardt's patients. [2]

Contents

In cancer studies, Fenretinide treatment may cause ceramide (a wax-like substance) to build up in tumor cells and is associated with the accumulation of reactive oxygen species (ROS), resulting in cell death through apoptosis and/or necrosis. [3] Fenretinide accumulates preferentially in fatty tissue such as the breast, which may contribute to the effectiveness of fenretinide against breast cancer. [4] [5] Phase III clinical trial data has suggested that fenretinide reduces breast cancer relapse in pre-menopausal women. [6] Common side effects associated with fenretinide treatment include skin dryness and night-blindness, which is reversible upon cessation of treatment. Specific types of cancer under investigation include or have included ovarian, prostate, cervical, lung, renal, bladder, breast, glioma, skin, head and neck carcinoma, non-Hodgkin's lymphoma, neuroblastoma, and Ewing's sarcoma.

Synthesis

ChemDrug Synthesis: Patent (Ex IX): Additional literature: etc. Fenretinide synthesis.svg
ChemDrug Synthesis: Patent (Ex IX): Additional literature: etc.

A Schotten-Baumann amidation of ATRA with p-aminophenol gives the anilide.

Related Research Articles

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References

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