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 No: 10-101-67

CAS No: 75921-69-6 (net)

Synonyms/Alias: Afamelanotide acetate;1566590-77-9;scenesse;Melanotan-1;Melanotan-1 acetate;CHEMBL4297213;TS-09692;

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

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC80H115N21O21
M.W/Mr.1706.9
SequenceOne Letter Code:SYSXEHFRWGKPV
Three Letter Code:Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2.CH3CO2H
Labeling TargetMelanocyte-stimulating hormone receptor
ApplicationAfamelanotide is a synthetic analog of α-melanocyte stimulating hormone (α-MSH). It act as a photoprotective agent by inducing skin pigmentation through melanogenesis.
AppearanceSolid powder
Areas of InterestCancer
Cosmetic Peptides & Dermatology
Pituitary & Hypothalamic Hormones
FunctionsUbiquitin protein ligase binding
TargetMelanocyte-stimulating hormone receptor
Source#Synthetic
Long-term Storage ConditionsSoluble in DMSO
Shipping ConditionShipped 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 ConditionsDry, dark and at 0 - 4 °C
OrganismHuman
InChIInChI=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 KeyLBIUKNXYUXOWFF-CRYSLBJVSA-N
Canonical SMILESCCCCC(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 SMILESCCCC[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
BoilingPointN/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 PointN/A

1. GLP-1, exendin-4 and C-peptide regulate pancreatic islet microcirculation, insulin secretion and glucose tolerance in rats

2. Novel Peptide-Based PD1 Immunomodulators Demonstrate Efficacy in Infectious Disease Vaccines and Therapeutics

3. Immune responses to peptides containing homocitrulline or citrulline in the DR4-transgenic mouse model of rheumatoid arthritis

4. Myotropic activity of allatostatins in tenebrionid beetles

5. A possible role of tachykinin-related peptide on an immune system activity of mealworm beetle, Tenebrio molitor L

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