AM580
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MedKoo CAT#: 407305

CAS#: 102121-60-8

Description: AM-580 is a potent RARalpha agonist. AM580 has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells. AM580 inhibited the wnt pathway, measured by loss of nuclear beta-catenin, suggesting partial oncogene dependence of therapy. Am580 treatment increased RARbeta and lowered the level of RARgamma, an isotype whose expression we linked with tumor proliferation. Specific activation of a single retinoic acid receptor-alpha (RARalpha), without direct and concurrent activation of RARbeta and gamma, will inhibit mammary tumor oncogenesis in murine models relevant to human cancer.

Chemical Structure

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AM580
CAS# 102121-60-8
Instruction

Theoretical Analysis

MedKoo Cat#: 407305
Name: AM580
CAS#: 102121-60-8
Chemical Formula: C22H25NO3
Exact Mass: 351.18
Molecular Weight: 351.446
Elemental Analysis: C, 75.19; H, 7.17; N, 3.99; O, 13.66

Price and Availability

Size Price Availability Quantity
100mg USD 190 2 Weeks
200mg USD 350 2 Weeks
500mg USD 750 2 Weeks
1g USD 1250 2 Weeks
2g USD 2250 2 Weeks
5g USD 4250 2 Weeks
Bulk inquiry

Synonym: AM-580; AM 580; AM580.

IUPAC/Chemical Name: 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamido)benzoic acid

InChi Key: SZWKGOZKRMMLAJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)

SMILES Code: O=C(O)C1=CC=C(NC(C2=CC=C3C(C)(C)CCC(C)(C)C3=C2)=O)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 351.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Cai A, Lin Z, Liu N, Li X, Wang J, Wu Y, Gao K, Jiang Y. Neuroblastoma SH- SY5Y Cell Differentiation to Mature Neuron by AM580 Treatment. Neurochem Res. 2022 Dec;47(12):3723-3732. doi: 10.1007/s11064-022-03730-w. Epub 2022 Sep 6. PMID: 36066699; PMCID: PMC9718880.


2: Gianní M, Li Calzi M, Terao M, Guiso G, Caccia S, Barbui T, Rambaldi A, Garattini E. AM580, a stable benzoic derivative of retinoic acid, has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells. Blood. 1996 Feb 15;87(4):1520-31. PMID: 8608243.


3: Wang Q, Thome R, Rostami A, Ma CG, Zhang GX. The selective retinoic acid receptor-α agonist AM580 fails to control autoimmune neuroinflammation. Cell Mol Immunol. 2019 Aug;16(8):727-729. doi: 10.1038/s41423-019-0238-9. Epub 2019 Jun 3. PMID: 31160758; PMCID: PMC6804666.


4: Zhang S, Wang J, Cheng G. Protease cleavage of RNF20 facilitates coronavirus replication via stabilization of SREBP1. Proc Natl Acad Sci U S A. 2021 Sep 14;118(37):e2107108118. doi: 10.1073/pnas.2107108118. PMID: 34452991; PMCID: PMC8449311.


5: Lu Y, Bertran S, Samuels TA, Mira-y-Lopez R, Farias EF. Mechanism of inhibition of MMTV-neu and MMTV-wnt1 induced mammary oncogenesis by RARalpha agonist AM580. Oncogene. 2010 Jun 24;29(25):3665-76. doi: 10.1038/onc.2010.119. Epub 2010 May 10. PMID: 20453882; PMCID: PMC2891995.


6: Bosch A, Bertran SP, Lu Y, Garcia A, Jones AM, Dawson MI, Farias EF. Reversal by RARα agonist Am580 of c-Myc-induced imbalance in RARα/RARγ expression during MMTV-Myc tumorigenesis. Breast Cancer Res. 2012 Aug 24;14(4):R121. doi: 10.1186/bcr3247. PMID: 22920668; PMCID: PMC3680916.


7: Tacke R, Müller V, Büttner MW, Lippert WP, Bertermann R, Daiss JO, Khanwalkar H, Furst A, Gaudon C, Gronemeyer H. Synthesis and pharmacological characterization of Disila-AM80 (Disila-tamibarotene) and Disila-AM580, silicon analogues of the RARalpha-selective retinoid agonists AM80 (Tamibarotene) and AM580. ChemMedChem. 2009 Nov;4(11):1797-802. doi: 10.1002/cmdc.200900257. PMID: 19790202.


8: Tamura K, Kagechika H, Hashimoto Y, Shudo K, Ohsugi K, Ide H. Synthetic retinoids, retinobenzoic acids, Am80, Am580 and Ch55 regulate morphogenesis in chick limb bud. Cell Differ Dev. 1990 Oct;32(1):17-26. doi: 10.1016/0922-3371(90)90095-e. PMID: 2090329.


9: Cheng YH, Utsunomiya H, Pavone ME, Yin P, Bulun SE. Retinoic acid inhibits endometrial cancer cell growth via multiple genomic mechanisms. J Mol Endocrinol. 2011 Mar 23;46(2):139-53. doi: 10.1530/JME-10-0064. PMID: 21310893; PMCID: PMC4511599.


10: Dimitrova B, Caccia S, Garattini E, Guiso G. Determination of the retinobenzoic acid derivative Am580 in rat plasma by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1995 May 19;667(2):301-6. doi: 10.1016/0378-4347(95)00014-a. PMID: 7663703.


11: Tanabe K, Utsunomiya H, Tamura M, Niikura H, Takano T, Yoshinaga K, Nagase S, Suzuki T, Ito K, Matsumoto M, Hayashi S, Yaegashi N. Expression of retinoic acid receptors in human endometrial carcinoma. Cancer Sci. 2008 Feb;99(2):267-71. doi: 10.1111/j.1349-7006.2007.00684.x. PMID: 18271925.


12: Ganz T, Fainstein N, Elad A, Lachish M, Goldfarb S, Einstein O, Ben-Hur T. Microbial pathogens induce neurodegeneration in Alzheimer's disease mice: protection by microglial regulation. J Neuroinflammation. 2022 Jan 6;19(1):5. doi: 10.1186/s12974-021-02369-8. PMID: 34991645; PMCID: PMC8740456.


13: Yuan S, Chu H, Chan JF, Ye ZW, Wen L, Yan B, Lai PM, Tee KM, Huang J, Chen D, Li C, Zhao X, Yang D, Chiu MC, Yip C, Poon VK, Chan CC, Sze KH, Zhou J, Chan IH, Kok KH, To KK, Kao RY, Lau JY, Jin DY, Perlman S, Yuen KY. SREBP-dependent lipidomic reprogramming as a broad-spectrum antiviral target. Nat Commun. 2019 Jan 10;10(1):120. doi: 10.1038/s41467-018-08015-x. PMID: 30631056; PMCID: PMC6328544.


14: Goldfarb S, Fainstein N, Ganz T, Vershkov D, Lachish M, Ben-Hur T. Electric neurostimulation regulates microglial activation via retinoic acid receptor α signaling. Brain Behav Immun. 2021 Aug;96:40-53. doi: 10.1016/j.bbi.2021.05.007. Epub 2021 May 12. PMID: 33989746.


15: Willhite CC, Dawson MI, Reichert U. Receptor-selective retinoid agonists and teratogenic activity. Drug Metab Rev. 1996 Feb-May;28(1-2):105-19. doi: 10.3109/03602539608993994. PMID: 8744592.


16: Milonas D, Tziomalos K. Experimental therapies targeting apolipoprotein C-III for the treatment of hyperlipidemia - spotlight on volanesorsen. Expert Opin Investig Drugs. 2019 Apr;28(4):389-394. doi: 10.1080/13543784.2019.1582028. Epub 2019 Feb 15. PMID: 30753100.


17: Lee SJ, Mahankali M, Bitar A, Zou H, Chao E, Nguyen H, Gonzalez J, Caballero D, Hull M, Wang D, Schultz PG, Shen W. A Novel Role for RARα Agonists as Apolipoprotein CIII Inhibitors Identified from High Throughput Screening. Sci Rep. 2017 Jul 19;7(1):5824. doi: 10.1038/s41598-017-05163-w. PMID: 28724938; PMCID: PMC5517646.


18: Kimura K, Zhou H, Orita T, Kobayashi M, Nishida T, Sonoda KH. Suppression by an RAR-γ Agonist of Collagen Degradation Mediated by Corneal Fibroblasts. Invest Ophthalmol Vis Sci. 2017 Apr 1;58(4):2250-2257. doi: 10.1167/iovs.15-18701. PMID: 28418498.


19: Ratnam KK, Feng X, Chuang PY, Verma V, Lu TC, Wang J, Jin Y, Farias EF, Napoli JL, Chen N, Kaufman L, Takano T, D'Agati VD, Klotman PE, He JC. Role of the retinoic acid receptor-α in HIV-associated nephropathy. Kidney Int. 2011 Mar;79(6):624-634. doi: 10.1038/ki.2010.470. Epub 2010 Dec 8. PMID: 21150871; PMCID: PMC3050085.


20: Kagechika H. Novel synthetic retinoids and separation of the pleiotropic retinoidal activities. Curr Med Chem. 2002 Mar;9(5):591-608. doi: 10.2174/0929867024606975. PMID: 11945126.