Afamelanotide is a first-in-class, synthetic, 13-amino acid peptide analogue of the endogenous alpha melanocyte-stimulating hormone (α-MSH). It differs structurally from its endogenous counterpart by only two amino acids - these structural differences improve biological efficacy by imparting a greater affinity for its target and a longer biological half-life.
CAT# | R1512 |
Chemical Structure | |
CAS | 75921-69-6 |
Synonyms/Alias | alpha-NDP-MSH; [Nle4,dPhe7]alpha-MSH; N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-norleucyl-L-alpha-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-glycyl-L-lysyl-L-prolyl-L-valinamide; Melanotan I; Melanotan-I |
Chemical Name | (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid |
M.F/Formula | C78H111N21O19 |
M.W/Mr. | 1646.8 |
Sequence | One Letter Code: SYSXEHFRWGKPV Three Letter Code: Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 |
Activity | Agonist |
Biological Activity | Synthetic analog of α-MSH that is an agonist at melanocortin receptors (Ki values are 0.085, 0.4, 3.8 and 5.1 nM for MC1, MC3, MC4 and MC5 receptors respectively). |
Target | Melanocyte-stimulating hormone receptor |
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