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MedKoo Cat#: 530608 | Name: BMS-470539

Description:

WARNING: This product is for research use only, not for human or veterinary use.

BMS-470539 is a melanocortin MC(1) receptor agonist. BMS-470539 inhibits leucocyte trafficking in the inflamed vasculature. Activation of Melanocortin Receptors MC 1 and MC 5 Attenuates Retinal Damage in Experimental Diabetic Retinopathy.

Chemical Structure

BMS-470539
CAS#457893-92-4 (free base)

Theoretical Analysis

MedKoo Cat#: 530608

Name: BMS-470539

CAS#: 457893-92-4 (free base)

Chemical Formula: C32H41N5O4

Exact Mass: 559.3159

Molecular Weight: 559.71

Elemental Analysis: C, 68.67; H, 7.38; N, 12.51; O, 11.43

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
457893-92-4 (free base) 2341796-82-3 (HCl)
Synonym
BMS-470539; BMS470539; BMS 470539.
IUPAC/Chemical Name
(S)-2-amino-N-((R)-1-(4-butyryl-4-phenylpiperidin-1-yl)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)-3-(1-methyl-1H-imidazol-5-yl)propanamide
InChi Key
GULVVTHHUIIMRL-WUFINQPMSA-N
InChi Code
InChI=1S/C32H41N5O4/c1-4-8-29(38)32(24-9-6-5-7-10-24)15-17-37(18-16-32)31(40)28(19-23-11-13-26(41-3)14-12-23)35-30(39)27(33)20-25-21-34-22-36(25)2/h5-7,9-14,21-22,27-28H,4,8,15-20,33H2,1-3H3,(H,35,39)/t27-,28+/m0/s1
SMILES Code
N[C@@H](CC1=CN=CN1C)C(N[C@@H](C(N2CCC(C3=CC=CC=C3)(CC2)C(CCC)=O)=O)CC4=CC=C(C=C4)OC)=O
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 559.71 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
1: Yu S, Doycheva DM, Gamdzyk M, Gao Y, Guo Y, Travis ZD, Tang J, Chen WX, Zhang JH. BMS-470539 Attenuates Oxidative Stress and Neuronal Apoptosis via MC1R/cAMP/PKA/Nurr1 Signaling Pathway in a Neonatal Hypoxic-Ischemic Rat Model. Oxid Med Cell Longev. 2022 Jan 31;2022:4054938. doi: 10.1155/2022/4054938. PMID: 35140838; PMCID: PMC8820941. 2: Gesualdo C, Balta C, Platania CBM, Trotta MC, Herman H, Gharbia S, Rosu M, Petrillo F, Giunta S, Della Corte A, Grieco P, Bellavita R, Simonelli F, D'Amico M, Hermenean A, Rossi S, Bucolo C. Fingolimod and Diabetic Retinopathy: A Drug Repurposing Study. Front Pharmacol. 2021 Sep 17;12:718902. doi: 10.3389/fphar.2021.718902. PMID: 34603029; PMCID: PMC8484636. 3: Yu S, Doycheva DM, Gamdzyk M, Yang Y, Lenahan C, Li G, Li D, Lian L, Tang J, Lu J, Zhang JH. Activation of MC1R with BMS-470539 attenuates neuroinflammation via cAMP/PKA/Nurr1 pathway after neonatal hypoxic-ischemic brain injury in rats. J Neuroinflammation. 2021 Jan 19;18(1):26. doi: 10.1186/s12974-021-02078-2. PMID: 33468172; PMCID: PMC7814630. 4: Fan K, Zeng L, Guo J, Xie S, Yu Y, Chen J, Cao J, Xiang Q, Zhang S, Luo Y, Deng Q, Zhou Q, Zhao Y, Hao L, Wang Z, Zhong L. Visualized podocyte-targeting and focused ultrasound responsive glucocorticoid nano-delivery system against immune-associated nephropathy without glucocorticoid side effect. Theranostics. 2021 Jan 1;11(6):2670-2690. doi: 10.7150/thno.53083. PMID: 33456566; PMCID: PMC7806481. 5: Xu W, Yan J, Ocak U, Lenahan C, Shao A, Tang J, Zhang J, Zhang JH. Melanocortin 1 receptor attenuates early brain injury following subarachnoid hemorrhage by controlling mitochondrial metabolism via AMPK/SIRT1/PGC-1α pathway in rats. Theranostics. 2021 Jan 1;11(2):522-539. doi: 10.7150/thno.49426. PMID: 33391490; PMCID: PMC7738864. 6: Montero-Melendez T, Nagano A, Chelala C, Filer A, Buckley CD, Perretti M. Therapeutic senescence via GPCR activation in synovial fibroblasts facilitates resolution of arthritis. Nat Commun. 2020 Feb 6;11(1):745. doi: 10.1038/s41467-020-14421-x. PMID: 32029712; PMCID: PMC7005314. 7: Can VC, Locke IC, Kaneva MK, Kerrigan MJP, Merlino F, De Pascale C, Grieco P, Getting SJ. Novel anti-inflammatory and chondroprotective effects of the human melanocortin MC1 receptor agonist BMS-470539 dihydrochloride and human melanocortin MC3 receptor agonist PG-990 on lipopolysaccharide activated chondrocytes. Eur J Pharmacol. 2020 Apr 5;872:172971. doi: 10.1016/j.ejphar.2020.172971. Epub 2020 Jan 28. PMID: 32004526. 8: Jang EA, Kim JY, Tin TD, Song JA, Lee SH, Kwak SH. The effects of BMS-470539 on lipopolysaccharide-induced acute lung injury. Acute Crit Care. 2019 May;34(2):133-140. doi: 10.4266/acc.2019.00507. Epub 2019 May 31. PMID: 31723918; PMCID: PMC6786663. 9: Xu W, Mo J, Ocak U, Travis ZD, Enkhjargal B, Zhang T, Wu P, Peng J, Li T, Zuo Y, Shao A, Tang J, Zhang J, Zhang JH. Activation of Melanocortin 1 Receptor Attenuates Early Brain Injury in a Rat Model of Subarachnoid Hemorrhage viathe Suppression of Neuroinflammation through AMPK/TBK1/NF-κB Pathway in Rats. Neurotherapeutics. 2020 Jan;17(1):294-308. doi: 10.1007/s13311-019-00772-x. PMID: 31486022; PMCID: PMC7007470. 10: Lee S, Ju W, Tin TD, Kim J, Lee JS, Park CH, Kwak SH. Effect of BMS-470539 on lipopolysaccharide-induced neutrophil activation. Korean J Anesthesiol. 2020 Apr;73(2):151-157. doi: 10.4097/kja.19233. Epub 2019 Aug 3. PMID: 31378052; PMCID: PMC7113170. 11: Maisto R, Oltra M, Vidal-Gil L, Martínez-Gil N, Sancho-Pellúz J, Filippo CD, Rossi S, D Amico M, Barcia JM, Romero FJ. ARPE-19-derived VEGF-containing exosomes promote neovascularization in HUVEC: the role of the melanocortin receptor 5. Cell Cycle. 2019 Feb;18(4):413-424. doi: 10.1080/15384101.2019.1568745. Epub 2019 Feb 9. PMID: 30739530; PMCID: PMC6422460. 12: Patruno S, Garrido-Mesa J, Romano M, Perretti M, Montero-Melendez T. Ligand Bias and Its Association With Pro-resolving Actions of Melanocortin Drugs. Front Pharmacol. 2018 Aug 14;9:919. doi: 10.3389/fphar.2018.00919. PMID: 30154720; PMCID: PMC6102781. 13: Rossi S, Maisto R, Gesualdo C, Trotta MC, Ferraraccio F, Kaneva MK, Getting SJ, Surace E, Testa F, Simonelli F, Grieco P, Merlino F, Perretti M, D'Amico M, Di Filippo C. Activation of Melanocortin Receptors MC 1 and MC 5 Attenuates Retinal Damage in Experimental Diabetic Retinopathy. Mediators Inflamm. 2016;2016:7368389. doi: 10.1155/2016/7368389. Epub 2016 Jan 12. Erratum in: Mediators Inflamm. 2021 Mar 30;2021:9861434. PMID: 26949291; PMCID: PMC4753692. 14: Lindskog Jonsson A, Granqvist A, Elvin J, Johansson ME, Haraldsson B, Nyström J. Effects of melanocortin 1 receptor agonists in experimental nephropathies. PLoS One. 2014 Jan 30;9(1):e87816. doi: 10.1371/journal.pone.0087816. PMID: 24498203; PMCID: PMC3907561. 15: Doyle JR, Fortin JP, Beinborn M, Kopin AS. Selected melanocortin 1 receptor single-nucleotide polymorphisms differentially alter multiple signaling pathways. J Pharmacol Exp Ther. 2012 Aug;342(2):318-26. doi: 10.1124/jpet.112.194548. Epub 2012 Apr 30. PMID: 22547573; PMCID: PMC3400803. 16: Leoni G, Voisin MB, Carlson K, Getting S, Nourshargh S, Perretti M. The melanocortin MC(1) receptor agonist BMS-470539 inhibits leucocyte trafficking in the inflamed vasculature. Br J Pharmacol. 2010 May;160(1):171-80. doi: 10.1111/j.1476-5381.2010.00688.x. Epub 2010 Mar 19. PMID: 20331604; PMCID: PMC2860217. 17: Kang L, McIntyre KW, Gillooly KM, Yang Y, Haycock J, Roberts S, Khanna A, Herpin TF, Yu G, Wu X, Morton GC, Tuerdi H, Koplowitz B, Walker SG, Wardwell- Swanson J, Macor JE, Lawrence RM, Carlson KE. A selective small molecule agonist of the melanocortin-1 receptor inhibits lipopolysaccharide-induced cytokine accumulation and leukocyte infiltration in mice. J Leukoc Biol. 2006 Oct;80(4):897-904. doi: 10.1189/jlb.1204748. Epub 2006 Aug 3. PMID: 16888084.

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