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Identification
Name Fenretinide
Accession Number DB05076 (DB03922)
Type small molecule
Groups
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
4-HPR
4-hydroxy(phenyl)retinamide
N-(4-Hydroxyphenyl)All-Trans Retinamide
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Antineoplastic Agents
  • Anticarcinogenic Agents
CAS number 65646-68-6
Weight Average: 391.5457
Monoisotopic: 391.251129305
Chemical Formula C26H33NO2
InChI Key InChIKey=AKJHMTWEGVYYSE-FXILSDISSA-N
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+
Plain Text
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
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(=O)NC1=CC=C(O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Investigated for use/treatment in macular degeneration.
Pharmacodynamics Not Available
Mechanism 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity "Mechanism of fenretinide (4-HPR)-induced cell death"
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 1.19e-03 g/l ALOGPS
logP 6.31 ALOGPS
logP 6.15 ChemAxon
logS -5.5 ALOGPS
pKa (strongest acidic) 9.45 ChemAxon
pKa (strongest basic) -1.2 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 49.33 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 128.05 ChemAxon
polarizability 47.58 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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. 2007 Dec 8;. Pubmed
  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
  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
External Links
Resource Link
KEGG Drug D04162 Link_out
PubChem Compound 5288209 Link_out
PubChem Substance 10388780 Link_out
ChemSpider 4450416 Link_out
HET FEN Link_out
Wikipedia http://en.wikipedia.org/wiki/Fenretinide Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Carriers

1. Plasma retinol-binding protein

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

UniProt ID: P02753 Link_out
Gene: RBP4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  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
  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
  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
Comments
Drug created on October 21, 2007 16:23 / Updated on February 08, 2013 16:23