Afamelanotide acetate

Afamelanotide is an analog of the peptide hormone alpha-melanocyte stimulating hormone (alpha-MSH), which tends to induce skin tanning.

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CAT#	10-101-67
CAS	75921-69-6 (net)
Background	Afamelanotide is a synthetic peptide analogue of the naturally occurring alpha-melanocyte stimulating hormone (a-MSH) with potential photoprotective activity. Mimicking the action of a-MSH, afamelanotide stimulates melanocytes to increase the production and release of melanin. Increased melanocyte melanin may protect against ultraviolet radiation (UVR)-initiated cellular DNA damage, oxidation of membrane proteins, and alterations in intracellular signaling processes in epidermal cells. Endogenously, a-MSH is released by skin cells in response to UVR exposure, stimulating melanocytes to produce and release melanin. >> Read More
Synonyms/Alias	(Nle4,D-Phe7)-α-MSH; NDP-MSH; Melanotan 1; CUV1647;Melanotan-1;MT-1;MT1;MT 1;MBJ 05; Afamelanotide acetate; CUV 1647; CUV-1647; CUV1647
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-4-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;acetic acid
M.F/Formula	C78H111N21O19
M.W/Mr.	1646.85
Sequence	Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2
Labeling Target	Melanocyte-stimulating hormone receptor
Application	Afamelanotide is a synthetic analog of α-melanocyte stimulating hormone (α-MSH). It act as a photoprotective agent by inducing skin pigmentation through melanogenesis.
Appearance	Solid powder
Areas of Interest	Cancer Cosmetic Peptides & Dermatology Pituitary & Hypothalamic Hormones
Functions	Ubiquitin protein ligase binding
Target	Melanocyte-stimulating hormone receptor

CAT#	Product Name	M.W	Molecular Formula	Inquiry
10-101-02	Alarelin acetate	1287.44	C60H86N16O16	Inquiry
10-101-06	Bivalirudin Trifluoroacetate	2180.32	C98H138N24O33	Inquiry
10-101-106	Acetylcysteine Ph. Eur.	163.2	C5H9NO3S	Inquiry

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Source#	Synthetic
Solubility	Soluble in DMSO
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.
Short-term Storage Conditions	Dry, dark and at 0 - 4 °C
Organism	Human
InChI	InChI=1S/C78H111N21O19.C2H4O2/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107;1-2(3)4/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84);1H3,(H,3,4)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-;/m0./s1
InChI Key	LBIUKNXYUXOWFF-CRYSLBJVSA-N
Canonical SMILES	CCCCC(C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CNC=N1)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)NC(CCCCN)C(=O)N5CCCC5C(=O)NC(C(C)C)C(=O)N)NC(=O)C(CO)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CO)NC(=O)C.CC(=O)O
Isomeric SMILES	CCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N5CCC[C@H]5C(=O)N[C@@H](C(C)C)C(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](CO)NC(=O)C.CC(=O)O
BoilingPoint	N/A
References	Vitiligo is characterized by depigmented patches of skin due to loss of cutaneous melanocytes. Many recent studies have demonstrated defects in the melanocortin system in patients with vitiligo, including decreased circulating and lesional skin levels of α-melanocyte-stimulating hormone (α-MSH). Afamelanotide is a potent and longer-lasting synthetic analogue of naturally occurring α-MSH. Grimes P E, Hamzavi I, Lebwohl M, et al. The efficacy of afamelanotide and narrowband UV-B phototherapy for repigmentation of vitiligo[J]. JAMA dermatology, 2013, 149(1): 68-73. Narrowband UV-B (NB-UV-B) phototherapy is used extensively to treat vitiligo. Afamelanotide, an analogue of α-melanocyte-stimulating hormone, is known to induce tanning of the skin. Lim H W, Grimes P E, Agbai O, et al. Afamelanotide and narrowband UV-B phototherapy for the treatment of vitiligo: a randomized multicenter trial[J]. JAMA dermatology, 2015, 151(1): 42-50. Erythropoietic protoporphyria is a severe photodermatosis that is associated with acute phototoxicity. Patients with this condition have excruciating pain and a markedly reduced quality of life. We evaluated the safety and efficacy of an α-melanocyte-stimulating hormone analogue, afamelanotide, to decrease pain and improve quality of life. Langendonk J G, Balwani M, Anderson K E, et al. Afamelanotide for erythropoietic protoporphyria[J]. New England Journal of Medicine, 2015, 373(1): 48-59.
Melting Point	N/A