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Accession NumberDB05076  (DB03922)
TypeSmall Molecule
DescriptionA 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.
N-(4-Hydroxyphenyl)All-Trans Retinamide
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CAS number65646-68-6
WeightAverage: 391.5457
Monoisotopic: 391.251129305
Chemical FormulaC26H33NO2
IndicationInvestigated for use/treatment in macular degeneration.
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionFenretinide 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity"Mechanism of fenretinide (4-HPR)-induced cell death"
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Drug Interactions
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Fenretinide.
BevacizumabBevacizumab may increase the cardiotoxic activities of Fenretinide.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Fenretinide.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Fenretinide.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Fenretinide.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Fenretinide.
DigoxinDigoxin may decrease the cardiotoxic activities of Fenretinide.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Fenretinide.
OuabainOuabain may decrease the cardiotoxic activities of Fenretinide.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Fenretinide.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Fenretinide.
Food InteractionsNot Available
Synthesis ReferenceNot Available
General References
  1. 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. 2008 Sep;62(4):655-65. Epub 2007 Dec 8. [PubMed:18066548 ]
  2. 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:17955489 ]
  3. Simeone AM, Tari AM: How retinoids regulate breast cancer cell proliferation and apoptosis. Cell Mol Life Sci. 2004 Jun;61(12):1475-84. [PubMed:15197471 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Predicted ADMET features
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.7618
Caco-2 permeable+0.6523
P-glycoprotein substrateNon-substrate0.5141
P-glycoprotein inhibitor INon-inhibitor0.7389
P-glycoprotein inhibitor IIInhibitor0.6346
Renal organic cation transporterNon-inhibitor0.8486
CYP450 2C9 substrateNon-substrate0.7527
CYP450 2D6 substrateNon-substrate0.7217
CYP450 3A4 substrateSubstrate0.7677
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.7136
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.6897
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7917
Ames testNon AMES toxic0.8418
BiodegradationNot ready biodegradable0.9225
Rat acute toxicity2.1836 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9585
hERG inhibition (predictor II)Non-inhibitor0.8054
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Experimental PropertiesNot Available
Predicted Properties
Water Solubility0.00119 mg/mLALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity128.05 m3·mol-1ChemAxon
Polarizability47.58 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
DescriptionThis compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
  • Retinoid skeleton
  • Diterpenoid
  • N-arylamide
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors


Pharmacological action
General Function:
Retinol transporter activity
Specific Function:
Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
Gene Name:
Uniprot ID:
Molecular Weight:
23009.8 Da
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on October 21, 2007 16:23 / Updated on August 17, 2016 12:24