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CAS No. :	102121-60-8
Formula :	C₂₂H₂₅NO₃
M.W :	351.44
SMILES Code :	O=C(O)C1=CC=C(NC(C2=CC=C3C(C)(C)CCC(C)(C)C3=C2)=O)C=C1
Synonyms :	CD336; Ro 40-6055; NSC608001
MDL No. :	MFCD00673916
InChI Key :	SZWKGOZKRMMLAJ-UHFFFAOYSA-N
Pubchem ID :	2126

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

A549 cells	20 µM	24 hours	AM580 significantly inhibited MERS-CoV replication in A549 cells	Nat Commun. 2019 Jan 10;10(1):120.
HEp-2 cells	20 µM	24 hours	AM580 significantly inhibited AdV5 replication in HEp-2 cells	Nat Commun. 2019 Jan 10;10(1):120.
RD cells	20 µM	24 hours	AM580 significantly inhibited EV-A71 replication in RD cells	Nat Commun. 2019 Jan 10;10(1):120.
Vero cells	20 µM	24 hours	AM580 significantly inhibited MERS-CoV replication in Vero cells	Nat Commun. 2019 Jan 10;10(1):120.
MDA-MB-231 cells	200 nM	48 hours	Increased RBP1 expression and atRA production	Cells. 2022 Feb 24;11(5):792.
MCF-7 cells	200 nM	48 hours	Increased RBP1 expression and atRA production	Cells. 2022 Feb 24;11(5):792.
HEK293T cells	100 µM		AM580 activated TRPV1-mediated calcium influx	J Clin Invest. 2013 Sep;123(9):3941-51.
Primary microglia	100 µM	12 hours	Am580 markedly attenuated TLR agonists-induced iNOS expression, without canceling their basic immune response.	J Neuroinflammation. 2022 Jan 6;19(1):5.
MMTV-wnt1 cells	50 nM	13 days	AM580 treatment increased caspase-3 expression in all of the colonies, and in 30% of the colonies induced acinar-like cavitation	Oncogene. 2010 Jun 24;29(25):3665-76.
THP-1 cells	20 µM	24 hours	AM580 significantly inhibited MERS-CoV replication in THP-1 cells	Nat Commun. 2019 Jan 10;10(1):120.
Calu-3 cells	20 µM	24 hours	AM580 significantly inhibited MERS-CoV replication in Calu-3 cells	Nat Commun. 2019 Jan 10;10(1):120.
Huh7 cells	20 µM	24 hours	AM580 significantly reduced MERS-CoV replication, viral titers decreased by >3-log10	Nat Commun. 2019 Jan 10;10(1):120.
ACE2-HeLa cells	20 µM	24 hours	AM580 significantly inhibited SARS-CoV-2 replication in ACE2-HeLa cells.	Proc Natl Acad Sci U S A. 2021 Sep 14;118(37):e2107108118.
Vero-E6 cells	20 µM	24 hours	AM580 significantly inhibited SARS-CoV-2 replication in Vero-E6 cells.	Proc Natl Acad Sci U S A. 2021 Sep 14;118(37):e2107108118.
Huh7 cells	20 µM	24 hours	AM580 treatment significantly inhibited SARS-CoV-2 replication, as demonstrated by a decrease in viral protein expression and viral RNA copies.	Proc Natl Acad Sci U S A. 2021 Sep 14;118(37):e2107108118.
MCF-7 cells	500 nM	24 hours	To evaluate the activation effect of AM580 on the RARβ promoter, results showed that AM580 significantly increased the activity of the RARβ promoter.	Cells. 2022 Mar 31;11(7):1179.
MDA-MB-231 cells	500 nM	24 hours	To evaluate the activation effect of AM580 on the RARβ promoter, results showed that AM580 significantly increased the activity of the RARβ promoter.	Cells. 2022 Mar 31;11(7):1179.
H-4-II-E rat hepatoma cells	1 nM to 1 µM	24 hours	To evaluate the effect of AM580 on CYP2C22 mRNA expression, results showed that AM580 significantly upregulated CYP2C22 mRNA levels.	J Lipid Res. 2010 Jul;51(7):1781-92.
Swan71 cells	200 nM	24 to 72 hours	To investigate the induction of RARRES1 expression by AM580 in Swan71 cells. Results showed that AM580 significantly induced RARRES1 expression.	J Exp Clin Cancer Res. 2017 Nov 23;36(1):165.
BeWo cells	200 nM	24 to 72 hours	To investigate the induction of RARRES1 expression by AM580 in BeWo cells. Results showed that AM580 alone did not significantly induce RARRES1 expression, but after pretreatment with 5-aza-2′-deoxycytidine, AM580 significantly increased RARRES1 expression.	J Exp Clin Cancer Res. 2017 Nov 23;36(1):165.
JAR cells	200 nM	24 to 72 hours	To investigate the induction of RARRES1 expression by AM580 in JAR cells. Results showed that AM580 alone did not significantly induce RARRES1 expression, but after pretreatment with 5-aza-2′-deoxycytidine, AM580 significantly increased RARRES1 expression.	J Exp Clin Cancer Res. 2017 Nov 23;36(1):165.
Jeg-3 cells	200 nM	24 to 72 hours	To investigate the induction of RARRES1 expression by AM580 in Jeg-3 cells. Results showed that AM580 alone did not significantly induce RARRES1 expression, but after pretreatment with 5-aza-2′-deoxycytidine, AM580 significantly increased RARRES1 expression.	J Exp Clin Cancer Res. 2017 Nov 23;36(1):165.
MDCK cells	20 µM	48 hours	AM580 significantly inhibited H1N1 virus replication in MDCK cells	Nat Commun. 2019 Jan 10;10(1):120.
Primary trophoblasts	200 nM	48 hours	To investigate the induction of RARRES1 expression by AM580 in primary trophoblasts. Results showed that AM580 significantly induced RARRES1 expression.	J Exp Clin Cancer Res. 2017 Nov 23;36(1):165.
Mouse mammary epithelial cells	200 nM	48 hours	To evaluate the effect of Am580 on CRBP1 expression, results showed that Am580 significantly induced CRBP1 protein expression	Breast Cancer Res. 2012 Aug 24;14(4):R121.
Monocyte-derived dendritic cells (moDCs)	100 nM	6 days	AM580 significantly enhanced the expression levels of ANKRD55 and upregulated IL31RA expression.	Front Immunol. 2022 Jan 17;12:816930.
HEK293T cells	1 µM	6 hours	To assess the metabolic capacity of CYP2C22 for RA, results showed that CYP2C22 converted RA to polar metabolites.	J Lipid Res. 2010 Jul;51(7):1781-92.
Human MCF-7 cells	200 nM	96 hours	To evaluate the effect of Am580 on cell proliferation, results showed that Am580 inhibited cell proliferation	Breast Cancer Res. 2012 Aug 24;14(4):R121.
Human MCF-10A cells	200 nM	96 hours	To evaluate the effect of Am580 on cell proliferation, results showed that Am580 inhibited cell proliferation	Breast Cancer Res. 2012 Aug 24;14(4):R121.
Mouse dorsal root ganglia neurons	5 µM		AM580 activated TRPV1-mediated currents and calcium influx	J Clin Invest. 2013 Sep;123(9):3941-51.

Zebrafish (Danio rerio)	Zebrafish embryos	Water exposure	0.001–0.03 µM	0–120 hpf (hours post-fertilization)	To evaluate the effect of AM580 on head skeleton malformations in zebrafish embryos. AM580 significantly increased the Meckel's–palatoquadrate (M–PQ) angle, indicating an effect on head skeleton development.	Arch Toxicol. 2018 Dec;92(12):3549-3564
Mice	MMTV-Myc transgenic mouse model	Oral	0.3 mg/kg/day	Daily administration for 50 weeks	To evaluate the effect of Am580 on mammary tumor growth and metastasis, results showed that Am580 significantly inhibited tumor growth and lung metastasis	Breast Cancer Res. 2012 Aug 24;14(4):R121.
Mice	Tg26 mice (HIV-1 transgenic mice)	Oral	0.3 mg/kg/day	Daily from the age of 4 weeks to 12 weeks	AM580 attenuated proteinuria, glomerulosclerosis, and podocyte proliferation, and restored podocyte differentiation markers	Kidney Int. 2011 Mar;79(6):624-634
Mice	MMTV-neu and MMTV-wnt1 transgenic mice	Dietary addition	0.3mg/kg/day	Daily, for 40 weeks (neu) and 35 weeks (wnt1)	AM580 treatment significantly increased tumor-free survival, reduced tumor incidence and growth of established tumors, and inhibited epithelial hyperplasia	Oncogene. 2010 Jun 24;29(25):3665-76.
HIV-1 transgenic mice	Rapidly progressive renal failure model	Mixed in the animal chow	0.3mg/kg/day	Daily for a total of 5 weeks	AM580 significantly reduced proteinuria, attenuated kidney injury, and improved podocyte differentiation. The renal protective effects were further enhanced when combined with the PDE4 inhibitor roflumilast.	Kidney Int. 2012 May;81(9):856-64
C57BL/6 mice	Experimental autoimmune encephalomyelitis (EAE)	Intraperitoneal injection	1 mg/kg or 2 mg/kg	Administered every other day, starting on day 11 post immunization until day 21 p.i.	AM580 was ineffective in suppressing EAE development and had no significant effect on demyelination and leukocyte infiltration	Cell Mol Immunol. 2019 Aug;16(8):727-729
Zucker diabetic fatty rats	Diabetic cardiomyopathy model	Oral gavage	1 mg/kg/day	Daily for 16 weeks	Am580 attenuated diabetes-induced cardiac dysfunction and the pathological alterations, by improving glucose tolerance and insulin resistance; facilitating Akt activation and glucose utilization, and attenuating oxidative stress and interrelated MAP kinase and NF-κB signaling pathways.	J Mol Cell Cardiol. 2013 Apr;57:106-18
Mice	Trpv1+/+ and Trpv1−/− mice	Intraplantar injection	100 nmol/20 μl	Single injection, observed for 2 hours	AM580 induced paw edema and nociceptive behaviors via TRPV1	J Clin Invest. 2013 Sep;123(9):3941-51.
HDPP4 transgenic mice	MERS-CoV infection model	Intraperitoneal injection	12.5 mg/kg/day	Once daily for 3 days	AM580 significantly improved the survival rate of MERS-CoV-infected mice, reduced body weight loss and lung viral load	Nat Commun. 2019 Jan 10;10(1):120.
5xFAD transgenic mice	Alzheimer's disease model	Intracerebroventricular delivery	28.5 mM	Continuous for 7 or 28 days	Intracerebroventricular delivery of Am580 in 5xFAD mice reduced significantly the fraction of (neurotoxic) iNOS + microglia and increased the fraction of (neuroprotective) TREM2 + microglia. Furthermore, intracerebroventricular delivery of Am580 prevented neurodegeneration induced by microbial TLR agonists.	J Neuroinflammation. 2022 Jan 6;19(1):5.
Rats	Vitamin A-deficient rats	Oral	30 µg AM580	Single dose, euthanized after 6 hours	To evaluate the effect of AM580 on CYP2C22 mRNA expression, results showed that AM580 significantly increased CYP2C22 mRNA levels.	J Lipid Res. 2010 Jul;51(7):1781-92.

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CAS No.: 102121-60-8

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CAS No.: 102121-60-8

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Precautionary Statements-General

Prevention

Response

Storage

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Physical hazards

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Preparing Stock Solutions		1mg	5mg	10mg
Preparing Stock Solutions	1 mM 5 mM 10 mM	2.85mL 0.57mL 0.28mL	14.23mL 2.85mL 1.42mL	28.45mL 5.69mL 2.85mL
Dissolving Methods	Animal experiment Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn: in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day; The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound. Protocol 1 Protocol 2

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