Nutlin-3a (Rebemadlin) | MDM2 Inhibitor

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CAS No. :	675576-98-4
Formula :	C₃₀H₃₀Cl₂N₄O₄
M.W :	581.49
SMILES Code :	O=C1NCCN(C(N2[C@H](C3=CC=C(Cl)C=C3)[C@H](C4=CC=C(Cl)C=C4)N=C2C5=CC=C(OC)C=C5OC(C)C)=O)C1
Synonyms :	Rebemadlin; (-)-Nutlin-3
MDL No. :	MFCD14636430
InChI Key :	BDUHCSBCVGXTJM-WUFINQPMSA-N
Pubchem ID :	11433190

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

SW 1990 cells	10 µM		Nutlin-3a, as an MDM2 inhibitor, inhibits MDM2-p53 interactions and stabilizes the p53 protein, thereby inducing cell autophagy and apoptosis.	PMC8895442
HPAC cells	10 µM		Nutlin-3a, as an MDM2 inhibitor, inhibits MDM2-p53 interactions and stabilizes the p53 protein, thereby inducing cell autophagy and apoptosis.	PMC8895442
HCT116 p21 KO cells	10 μM	8 h	Nutlin-3a treatment led to stabilization of p53 and restored the induction of PUMA in the presence of either growth factor.	PMC3076086
ALST cells	10 μM	24 h	To test the activation of WT TP53 by Nutlin-3a, results showed that Nutlin-3a increased WT TP53 activity.	PMC4656807
OVCA433 cells	10 μM	24 h	To test the activation of WT TP53 by Nutlin-3a, results showed that Nutlin-3a increased WT TP53 activity.	PMC4656807
OVCA420 cells	20 μM	24 h	To test the effect of Nutlin-3a on cell viability, results showed that OVCA420 cells were less sensitive to Nutlin-3a.	PMC4656807
OVCAR3 cells	20 μM	24 h	To test the effect of Nutlin-3a on cell viability, results showed that OVCAR3 cells were less sensitive to Nutlin-3a.	PMC4656807
HepG2 cells	10 µM		Nutlin-3a treatment increased ApoB expression and secretion and reduced lipid accumulation.	PMC9284139
Primary hepatocytes	10 µM		Nutlin-3a treatment increased ApoB expression and secretion and reduced lipid accumulation.	PMC9284139
LNCaP cells	0.5 μM	5 days	Nutlin-3a activates p53 signaling, inhibits LNCaP cell growth, and induces cell cycle arrest and apoptosis.	PMC3094321
22Rv1 cells	5 μM	48 h	Nutlin-3a combined with androgen deprivation enhanced the apoptotic response in 22Rv1 cells.	PMC3094321
DU145 cells	5 μM	48 h	No significant increase in apoptosis was observed in DU145 cells treated with Nutlin-3a.	PMC3094321
MCF-7 cells	8 μM	12 h	Using GRO-seq analysis, the production of enhancer RNAs (eRNAs) induced by nutlin-3a was detected, revealing p53-regulated enhancer regions.	PMC4389233
MCF-7 cells	8 μM	12 h	Through RNA sequencing, 194 nutlin-3a-responsive long non-coding RNAs (lncRNAs) were identified, and the importance of LED in the p53 transcriptional response was validated.	PMC4389233
PA-1 cells	40 μM	48 h	To evaluate the effect of Nutlin-3a on the p53 signaling pathway, results showed upregulation of p53 expression	PMC5695149
MCF-7 cells	40 μM	48 h	To evaluate the effect of Nutlin-3a on the p53 signaling pathway, results showed upregulation of p53 expression	PMC5695149
MDA-MB-231	15 µM	5 days	To evaluate the inhibitory effects of Nutlin-3a and carboplatin on cell proliferation, results showed that the combination of Nutlin-3a and carboplatin had a synergistic effect, significantly inhibiting cell proliferation	PMC4674357
TMD231	15 µM	5 days	To evaluate the inhibitory effects of Nutlin-3a and carboplatin on cell proliferation, results showed that the combination of Nutlin-3a and carboplatin had a synergistic effect, significantly inhibiting cell proliferation	PMC4674357
MDA-MB-468	15 µM	5 days	To evaluate the inhibitory effects of Nutlin-3a and carboplatin on cell proliferation, results showed that the combination of Nutlin-3a and carboplatin had a synergistic effect, significantly inhibiting cell proliferation	PMC4674357
MCF-7	15 µM	5 days	To evaluate the inhibitory effects of Nutlin-3a and carboplatin on cell proliferation, results showed that the combination of Nutlin-3a and carboplatin had a synergistic effect, significantly inhibiting cell proliferation	PMC4674357
U-2OS osteosarcoma cells	10 μM	14 days	Induced senescence rather than apoptosis	PMC3379802
HCT116 p53+/+ and HCT116 p53−/− cells	10 μM	24 hours	Detected p53 accumulation and down-regulation of ING2 expression in p53 wild-type cells	PMC3379802
HCT116 cells	5 μM	24 hours	Nutlin-3a treatment caused cell cycle arrest in G1 and G2 phases and promoted endoreduplication and the generation of tetraploid cells	PMC2674275
U2OS cells	5 μM	24 hours	Nutlin-3a treatment caused cell cycle arrest in G1 and G2 phases and promoted endoreduplication and the generation of tetraploid cells	PMC2674275

Mice	c-Myc-deficient mice	Gavage	200 mg/kg	Twice daily for 3 days, with the final dose 3 h before irradiation	Nutlin-3a treatment restored the apoptotic response in c-Myc-deficient mice, demonstrating that restoration of p53 function, via Nutlin treatment, is sufficient to rescue the blocked apoptosis phenotype in c-Myc-deficient enterocytes.	PMC4013513
Nude mice	Pancreatic cancer xenograft model	Intratumoral injection	100 mg/kg	Injected on days 1, 4, and 7, lasting for 21 days	Nutlin-3a, as an MDM2 inhibitor, enhanced the antipancreatic cancer effect of USP22 overexpression, significantly slowing tumor growth.	PMC8895442
mice	Whole body radiation (WBR) model	Intraperitoneal injection	10 mg/kg	1 hour after radiation	Nutlin-3a treatment restored the induction of PUMA and p53 in the presence of growth factors and significantly blocked the growth factor-mediated suppression of radiation-induced apoptosis.	PMC3076086
Mice	CDAHFD-induced steatohepatitis model	Intraperitoneal injection	10 mg/kg	Twice daily for 1-2 weeks	Nutlin-3a treatment alleviated CDAHFD-induced steatohepatitis by upregulating ApoB-mediated TG-VLDL secretion.	PMC9284139
nude mice	LNCaP xenograft model	oral	200 mg/kg	twice daily for 14 days	Nutlin-3a combined with androgen deprivation significantly enhanced antitumor activity, leading to complete tumor regression and dramatically increased survival in mice.	PMC3094321
Nude mice	PA-1 xenograft model	Intratumoral injection	10 mg/kg	Every other day for 3 weeks	To evaluate the tumor growth inhibitory effect of Nutlin-3a, results showed a tumor growth inhibition rate of 30%	PMC5695149
mice	TMD231 orthotopic mammary fat pad model	oral and intraperitoneal injection	200 mg/kg	twice weekly for 4 weeks	To evaluate the inhibitory effects of Nutlin-3a and carboplatin combination on primary tumor growth and lung metastasis, results showed that the combination treatment significantly inhibited tumor growth and lung metastasis with minimal toxicity to normal tissues	PMC4674357

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CAS No.: 675576-98-4

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CAS No.: 675576-98-4

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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