Fenretinide
(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
Molecular Identity
Fenretinide
(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
PubChem CID: 5288209
4-hydroxyphenyl retinamide is a retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids. It has a role as an antioxidant and an antineoplastic agent. It is a retinoid and a monocarboxylic acid amide. It is functionally related to an all-trans-retinoic acid.
2D Structure
Properties
C26H33NO2
Molecular Formula
391.50
Molecular Weight
g/mol
391.2511
Exact Mass
Da
7.3
XLogP
Above Lipinski threshold
49.3
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
2
H-Bond Acceptors
726
Complexity
SMILES
Canonical SMILES
SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)CIsomeric SMILES
SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NC2=CC=C(C=C2)O)/C)/CSynonyms(20)
FENRETINIDE65646-68-6N-(4-Hydroxyphenyl)retinamide4-HPR4-hydroxyphenylretinamide4-Hydroxyphenyl retinamideall-trans-4'-HydroxyretinanilideFenretinidaMcN-R-1967FenretinidumRetinamide, N-(4-hydroxyphenyl)-N-(4-Hydroxyphenyl)all-Trans Retinamide4-hydroxy(phenyl)retinamideRii retinamideDTXSID2032005
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Fenretinide
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