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Purity: ≥98%
Fenretinide (4-HPR), a synthetic retinoid deriverative, is a novel, potent and orally bioactive synthetic phenylretinamide analogue of retinol (vitamin A) with potential antineoplastic and chemopreventive activities. Fenretinide binds to and activates retinoic acid receptors (RARs), thereby inducing cell differentiation and apoptosis in some tumor cell types. This agent also inhibits tumor growth by modulating angiogenesis-associated growth factors and their receptors and exhibits retinoid receptor-independent apoptotic properties.
| ln Vitro |
In several T-ALL cell lines, fenretinide (4-HPR) exhibits both short-term and long-term anticancer action. In CCRF-CEM leukemia cells, fenretinide suppresses DES activity in a dose- and time-dependent manner, increasing endogenous cellular dhCer levels in the process. In CCRF-CEM and Jurkat cells, fenretinide (3 μM) causes an accumulation of dhCer [1]. Insulin signaling is protected by fenretinide's inhibition of ceramide. Insulin-stimulated glucose absorption is prevented from decreasing by lipids when fenretinide is present [2]. At concentrations above 1 microM, fenretinide decreases OVCAR-5 cell survival and proliferation; at 10 microM, it suppresses growth by 70–90%. After three days of preincubation, fenretinide (1 microM) dramatically reduced OVCAR-5 invasion. After being exposed to 1 µM 4-HPR, endothelial cells did not form tubes; instead, they produced tiny cell aggregates [4].
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| ln Vivo |
In male C57Bl/6 mice fed a high-fat diet, fenretinide (4-HPR) (10 mg/kg, ip) selectively prevents the build-up of ceramides. Tests for insulin and glucose tolerance show that fenretinide treatment increases insulin sensitivity and glucose tolerance [2]. The addition of 25 mg/kg ketoconazole to fenretinide raised the plasma levels of 4-HPR in NOD/SCID mice [3].
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| References |
[1]. Apraiz, Aintzane., et al. Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death. Biochemistry and Cell Biology (2012), 90(2), 209-223.
[2]. Bikman, Benjamin T., et al. Fenretinide Prevents Lipid-induced Insulin Resistance by Blocking Ceramide Biosynthesis. Journal of Biological Chemistry (2012), 287(21), 17426-17437. [3]. Cooper JP, et al. Fenretinide metabolism in humans and mice: utilizing pharmacological modulation of its metabolic pathway to increase systemic exposure. Br J Pharmacol. 2011 Jul;163(6):1263-75. [4]. Golubkov V, et al. Action of fenretinide (4-HPR) on ovarian cancer and endothelial cells. Anticancer Res. 2005 Jan-Feb;25(1A):249-53 |
| Molecular Formula |
C26H33NO2
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|---|---|
| Molecular Weight |
391.5457
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| CAS # |
65646-68-6
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| 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
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| InChi Key |
AKJHMTWEGVYYSE-FXILSDISSA-N
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| InChi Code |
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+
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| Chemical 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
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| Synonyms |
4-HPR McNR-1967 McNR1967 McNR 1967 HPR Fenretinide
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 130 mg/mL (~332.01 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.38 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.38 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.38 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5540 mL | 12.7698 mL | 25.5395 mL | |
| 5 mM | 0.5108 mL | 2.5540 mL | 5.1079 mL | |
| 10 mM | 0.2554 mL | 1.2770 mL | 2.5540 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT06181760 | Completed | Drug: Fenretinide Drug: Placebo |
Safety and Tolerability | Island Pharmaceuticals | November 22, 2023 | Phase 1 |
| NCT02141958 | Completed | Drug: Fenretinide Drug: Placebo |
Cystic Fibrosis | Elias Matouk | April 2014 | Phase 1 |
| NCT01553071 | Terminated | Drug: Fenretinide (4-HPR) plus Intravenous Safingol |
Solid Tumor | South Plains Oncology Consortium | November 2016 | Phase 1 |
| NCT01535157 | Terminated | Drug: Fenretinide/LXS + Ketoconazole | Ovarian Cancer Cancer of Ovary |
South Plains Oncology Consortium | February 2012 | Phase 1 Phase 2 |
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