BMS-470539

BMS-470539
Clinical data
Routes of; administration	S.C.
ATC code	None;
Legal status
Legal status	In general: non-regulated;
Pharmacokinetic data
Bioavailability	100% (with S.C. administration)
Elimination half-life	1.7 hours
Identifiers
	IUPAC name (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	457893-92-4 ;
ChemSpider	26232155 ;
CompTox Dashboard (EPA)	DTXSID60432747 ;
Chemical and physical data
Formula	C32H41N5O4
Molar mass	559.711 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC(=O)C1(CCN(CC1)C(=O)[C@@H](Cc2ccc(cc2)OC)NC(=O)[C@H](Cc3cncn3C)N)c4ccccc4;
	InChI 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 ; Key:DUAOBJHRUKFKIH-YDVFRNEYSA-N ;
	(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.

References

^ ^a ^b ^c ^d ^e ^f 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.
^ ^a ^b ^c 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.
^ 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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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
IUPAC name (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	457893-92-4^N
ChemSpider	26232155^Y
CompTox Dashboard (EPA)	DTXSID60432747
Chemical and physical data
Formula	C₃₂H₄₁N₅O₄
Molar mass	559.711 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCC(=O)C1(CCN(CC1)C(=O)[C@@H](Cc2ccc(cc2)OC)NC(=O)[C@H](Cc3cncn3C)N)c4ccccc4
InChI 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^Y Key:DUAOBJHRUKFKIH-YDVFRNEYSA-N^Y
^NY (what is this?) (verify)