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Fenretinide

CAT: 0013-GTR19161091-01Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161091-01Size:500 mg
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Description
Fenretinide (4-HPR) is a synthetic retinoid deriverative. 4-HBR is shown to exhibit binding to the retinoic acid receptors (RAR) at concentrations necessary to induce cell death. (In Vitro) :Fenretinide (4-HPR) exerts not just acute but also long term antitumor activity in selected T-ALL cell lines. Fenretinide inhibits DES activity in CCRF-CEM leukemia cells in a dose and time dependent manner, leading to a concomitant increase of the endogenous cellular dhCer content. Fenretinide (3 μM) -induced dhCer accumulation in both CCRF-CEM and Jurkat cells. Ceramide inhibition with fenretinide protects insulin signaling. Fenretinide prevents lipid-induced reductions in insulin-stimulated glucose uptake. Fenretinide inhibits OVCAR-5 cell proliferation and viability at concentrations higher than 1 microM, with 70-90% growth inhibition at 10 microM. Fenretinide (1 microM) significantly inhibits OVCAR-5 invasion after 3 days preincubation. Endothelial cells treated with 1 microM 4-HPR fails to form tubes, but forms small cellular aggregates. (In Vivo) :Fenretinide (4-HPR) (10 mg/kg, i.p.) selectively inhibits ceramide accumulation HFD-fed male C57Bl/6 mice. Fenretinide treatment improves glucose tolerance and insulin sensitivity as determined by both glucose and insulin tolerance tests. Addition of 25 mg/kg ketoconazole to Fenretinide in NOD/SCID mice increased 4-HPR plasma levels.
CAS Number
65646-68-6
Product Name Alternative
4-HPR | 4-Hydroxy (phenyl) retinamide | MK-4016 | Retinoic Acid p-hydroxyphenylamide | Ro 22-4667
Purity
>98% (HPLC)
Solubility
DMSO: ≥100mM
Smiles
O=C (NC1=CC=C (O) C=C1) /C=C (C) /C=C/C=C (C) /C=C/C2=C (C) CCCC2 (C) C
Molecular Formula
C26H33NO2
Molecular Weight
391.55
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(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

Chemical Information

Fenretinide

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.

CAS Number65646-68-6
PubChem CID5288209
IUPAC Name(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
Molecular FormulaC26H33NO2
Molecular Weight391.5
XLogP7.3
Topological Polar Surface Area49.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Heavy Atom Count29
Formal Charge0
Complexity726
SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NC2=CC=C(C=C2)O)/C)/C
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+
InChIKey
AKJHMTWEGVYYSE-FXILSDISSA-N
Chemical Structure
2D Structure
2D structure of Fenretinide
CAS: 65646-68-6
CID: 5288209
Formula: C26H33NO2
MW: 391.5
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight391.5
XLogP37.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass391.251129295
Monoisotopic Mass391.251129295
Topological Polar Surface Area49.3 Ų
Heavy Atom Count29
Formal Charge0
Complexity726
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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