Structure of 65646-68-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Fenretinide, the deriverative of retinoid, can bind to retinoic acid receptors (RAR) and induce cell death.
Synonyms: 4-HPR; Fenretinide; HPR
4.5
*For Research Use Only !
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 65646-68-6 |
Formula : | C26H33NO2 |
M.W : | 391.55 |
SMILES Code : | CC1=C(C(C)(CCC1)C)/C=C/C(C)=C/C=C/C(C)=C/C(NC2=CC=C(C=C2)O)=O |
Synonyms : |
4-HPR; Fenretinide; HPR
|
MDL No. : | MFCD00792674 |
InChI Key : | AKJHMTWEGVYYSE-FXILSDISSA-N |
Pubchem ID : | 5288209 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
TUBO cells | 5µM to 100µM | 72 h | To evaluate the effect of Bio-nFeR on TUBO cell viability, showing a dose-dependent inhibition of cell viability. | PMC11536529 |
MDA-MB-231 cells | 5µM to 100µM | 72 h | To evaluate the effect of Bio-nFeR on MDA-MB-231 cell viability, showing a dose-dependent inhibition of cell viability. | PMC11536529 |
MCF7 cells | 5µM to 100µM | 72 h | To evaluate the effect of Bio-nFeR on MCF7 cell viability, showing a dose-dependent inhibition of cell viability. | PMC11536529 |
RAW 264.7 cells | 0.1, 1, 10 μM | Fenretinide dose-dependently reduced M1 polarization in LOP-treated RAW 264.7 cells and decreased mRNA expression of M1 markers (iNos and Cox2) and pro-inflammatory cytokines (Tnfa and Il1b). | PMC9939369 | |
Rh30 cells | 4 μM | 48 h | To investigate the mechanism of Fenretinide-induced cell death, results showed that Fenretinide induces cell death through ROS production and cytoplasmic vacuolization | PMC7370225 |
Rh4 cells | 3 μM | 48 h | To investigate the mechanism of Fenretinide-induced cell death, results showed that Fenretinide induces cell death through ROS production and cytoplasmic vacuolization | PMC7370225 |
Human airway smooth-muscle cells | 5 μM | 5 h | To evaluate the effects of Fenretinide on sphingolipid metabolites in airway smooth-muscle cells. Results showed that Fenretinide increased sphinganine and dihydroceramides, and decreased intracellular calcium concentration. | PMC7605160 |
Human lung alveolar epithelial cell line A549 | 5 μM | 5 h | To evaluate the effects of Fenretinide on sphingolipid metabolites in lung cells. Results showed that Fenretinide increased sphinganine and dihydroceramides. | PMC7605160 |
Rat lung goblet cell line | 1.25 µM | Selectively prevents MUC5AC overexpression without significantly affecting MUC5B expression | PMC11105061 | |
CFBE 41o- cells | 1.25 µM | Selectively prevents MUC5AC overexpression without significantly affecting MUC5B expression | PMC11105061 | |
MCF7 cells | 5 μM | 4 h | Evaluate the effect of Fenretinide on CERK activity, found it suppresses NBD-C6-C1P production | PMC11326893 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
129 Sv mice | HER2/neu transgenic mouse model | Oral gavage | 100 mg/kg | 5 days/week, from week 14 to week 32 post-birth | To evaluate the effect of Bio-nFeR on mammary tumorigenesis and metastasis in HER2/neu transgenic mice, showing significant inhibition of tumor occurrence and metastasis. | PMC11536529 |
Mice | CFTR knockout mice | Not mentioned | 5–10 mg/kg | Not mentioned | Corrects pro-inflammatory lipid imbalance by decreasing AA levels and upregulating DHA levels | PMC11105061 |
Sprague-Dawley rats | Subcutaneous implantation model | Subcutaneous injection | 5% w/w | 1 month | Evaluate the in vivo release properties of PLGA-PVP-4HPR implants, showing that TEAC-PVP-4HPR PLGA implants achieved nearly complete release of 4HPR over 1 month | PMC7522920 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT02495415 | Peripheral T-cell Lymphoma | PHASE2 | UNKNOWN | 2025-12-21 | Banner MD Anderson Cancer Cent... More >>er, Gilbert, Arizona, 85234, United States|USC Norris Comprehensive Cancer Center, Los Angeles, California, 90033, United States|University of California, Los Angeles, Los Angeles, California, 90095, United States|Emory University, Atlanta, Georgia, 30322, United States|University of Kansas Cancer Center, Westwood, Kansas, 66205, United States|Norton Healthcare, Louisville, Kentucky, 40202, United States|University of Louisville, Louisville, Kentucky, 40202, United States|Hackensack University Medical Center, Hackensack, New Jersey, 07601, United States|Bon Secours Saint Francis Cancer Center, Greenville, South Carolina, 29607, United States|Baylor University Medical Center, Dallas, Texas, 75246, United States|University of Texas, Southwestern, Dallas, Texas, 75390, United States Less << |
NCT04234048 | T-cell Lymphoma|Cutaneous/Peri... More >>pheral T-Cell Lymphoma|Peripheral T-cell Lymphoma|Peripheral T-Cell Lymphoma, Not Classified|Primary Cutaneous T-cell Lymphoma|Cutaneous T-Cell Lymphoma, Unspecified|Cutaneous T-cell Lymphoma|Follicular T-Cell Lymphoma|Angioimmunoblastic T-cell Lymphoma|Sézary's Disease|Mycosis Fungoides Less << | PHASE1 | RECRUITING | 2025-11-25 | Mayo Clinic Arizona, Scottsdal... More >>e, Arizona, 85259, United States|City of Hope Medical Foundation, Duarte, California, 91010, United States|University of Southern California, Los Angeles, California, 90007, United States|University of Colorado Anschutz Medical Campus, Aurora, Colorado, 80045, United States|University of Michigan, Ann Arbor, Michigan, 48109, United States|Barbara Ann Karmanos Cancer Institute Wayne State University, Detroit, Michigan, 48201, United States|Columbia University, New York, New York, 10032, United States|University of Pittsburgh Medical Center (UPMC), Pittsburgh, Pennsylvania, 15219, United States|The University of Texas MD Anderson Cancer Center, Houston, Texas, 77030, United States Less << |
NCT00006471 | Head and Neck Cancer | PHASE2 | COMPLETED | 2025-07-04 | University of Texas - MD Ander... More >>son Cancer Center, Houston, Texas, 77030-4009, United States Less << |
NCT00429936 | Geographic Atrophy|Dry Age Rel... More >>ated Macular Degeneration Less << | PHASE2 | COMPLETED | 2025-05-10 | - |
Tags: Fenretinide | 4-HPR | RAR/RXR | Autophagy | Retinoic acid receptors | Retinoid X receptors | synthetic retinoid | anticancer | apoptosis | 65646-68-6
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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