BMS-470539

Last updated
BMS-470539
BMS 470539.svg
Clinical data
Routes of
administration 		S.C. [1]
ATC code
  • None
Legal status
Legal status
  • In general: non-regulated
Pharmacokinetic data
Bioavailability 100% (with S.C. administration) [1]
Elimination half-life 1.7 hours [1]
Identifiers
  • (2S)-2-amino-N-[(1R)-2-(4-butanoyl-4-phenyl-1-piperidyl)-1-[(4-methoxyphenyl)methyl]-2-oxo-ethyl]-3-(3-methylimidazol-4-yl)propanamide dihydrochloride
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C32H41N5O4
Molar mass 559.711 g·mol−1
3D model (JSmol)
  • CCCC(=O)C1(CCN(CC1)C(=O)[C@@H](Cc2ccc(cc2)OC)NC(=O)[C@H](Cc3cncn3C)N)c4ccccc4
  • InChI=1S/C32H41N5O4.2ClH/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);2*1H/t27-,28+;;/m0../s1 Yes check.svgY
  • Key:DUAOBJHRUKFKIH-YDVFRNEYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

BMS-470539 is a small-molecule experimental drug which acts as a potent and highly selective full agonist of the MC1 receptor. [1] [2] It was discovered in 2003 as part of an effort to understand the role of the MC1 receptor in immunomodulation, and has since been used in scientific research to determine its role in inflammatory processes. [1] [2] [3] The compound was designed with the intention of mimicking the central His-Phe-Arg-Trp pharmacophore of the melanocortins, [1] [2] and this proved to be successful based on its favorable pharmacodynamic profile.

See also

References

  1. 1 2 3 4 5 6 Kang L, McIntyre KW, Gillooly KM, et al. (October 2006). "A selective small molecule agonist of the melanocortin-1 receptor inhibits lipopolysaccharide-induced cytokine accumulation and leukocyte infiltration in mice". Journal of Leukocyte Biology. 80 (4): 897–904. doi:10.1189/jlb.1204748. PMID   16888084. S2CID   14196363. Archived from the original on 2013-04-15.
  2. 1 2 3 Herpin TF, Yu G, Carlson KE, et al. (March 2003). "Discovery of tyrosine-based potent and selective melanocortin-1 receptor small-molecule agonists with anti-inflammatory properties". Journal of Medicinal Chemistry. 46 (7): 1123–6. doi:10.1021/jm025600i. PMID   12646021.
  3. ↑ Leoni G, Voisin MB, Carlson K, Getting S, Nourshargh S, Perretti M (May 2010). "The melanocortin MC(1) receptor agonist BMS-470539 inhibits leucocyte trafficking in the inflamed vasculature". British Journal of Pharmacology. 160 (1): 171–80. doi:10.1111/j.1476-5381.2010.00688.x. PMC   2860217 . PMID   20331604.


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