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|Synonyms||Melanotan; Melanotan-1; Melanotan I; CUV1647; EPT1647; NDP-MSH; NDP-α-MSH; [Nle4,D-Phe7]α-MSH|
|AHFS/Drugs.com||UK Drug Information|
|S.C.; I.M.; I.V.; subcutaneous implant; intranasal|
|Elimination half-life||30 minutes|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||1646.845 g/mol g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Afamelanotide (melanotan I, CUV1647; brand name Scenesse) is a synthetic peptide and analogue of α-melanocyte stimulating hormone used to prevent skin damage from the sun in people with erythropoietic protoporphyria in Europe since January 2015 and the United States since October 2019. As a medicine sold under the brand name "Scenesse", it is administered in subcutaneous implant form; the implant lasts for two months.
It is under development in other skin disorders in several jurisdictions. It causes skin to turn darker by causing the skin to make more melanin.
It was discovered at University of Arizona and initially developed there as a sunless tanning agent; the Australian company Clinuvel conducted further clinical trials in that and other indications, and brought the drug to market in Europe and the United States.
Unlicensed and untested powders sold as "melanotan" are found on the Internet marketed for tanning and other purposes, and multiple regulatory bodies have warned consumers that the peptides may be unsafe and ineffective.
Afamelanotide is used in Europe to prevent phototoxicity in adults with erythropoietic protoporphyria (EPP). It is an implant that is injected and placed under the skin; an implant lasts two months.
People who have severe liver disease, liver impairment, or kidney impairment, should not use this drug. Pregnant women should not take it, and women who are active sexually should use contraception while they are taking it. It is not known if afamelanotide is secreted in breast milk.
Very common (up to 10% of people) adverse effects in people with EPP include headache and nausea. Common (between 1% and 10%) adverse effects include back pain, upper respiratory tract infections, decreased appetite, migraine, dizziness, weakness, fatigue, lethargy, sleepiness, feeling hot, stomach pain, diarrhea, vomiting, flushing and red skin, development of warts, spots, and freckles, itchy skin, and reactions at the injection site. There are many uncommon (less than 1%) adverse effects.
Afamelanotide has a half-life of 30 minutes. After the implant is injected, most of the drug is released within the first 2 days, with 90% released by the fifth day. By the tenth day no drug is detectable in plasma.
Its metabolites, distribution, metabolism and excretion were not understood as of 2017.
The amino acid sequence is Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2, and it is additionally known as [Nle4,D-Phe7]-α-MSH, which is sometimes abbreviated as NDP-MSH or NDP-α-MSH. Afamelanotide is the International Nonproprietary Name.
The role of α-MSH in promoting melanin diffusion has been known since the 1960s. In the 1980s, scientists at University of Arizona began attempting to develop α-MSH and analogs as potential sunless tanning agents, and synthesized and tested several analogs, including melanotan-I.
To pursue the tanning agent, melanotan-I was licensed by Competitive Technologies, a technology transfer company operating on behalf of University of Arizona, to an Australian startup called Epitan, which changed its name to Clinuvel in 2006.
Early clinical trials showed that the peptide had to be injected about ten times a day due to its short half-life, so the company collaborated with Southern Research in the US to develop a depot formulation that would be injected under the skin, and release the peptide slowly. This was done by 2004.
As of 2010, afamelanotide was in Phase III trials for erythropoietic protoporphyria and polymorphous light eruption, and was in Phase II trials for actinic keratosis and squamous cell carcinoma, and had been trialled in phototoxicity associated with systemic photodynamic therapy and solar urticaria. Clinuvel had also obtained orphan drug status for afamelanotide in the US and the EU by that time.
Society and culture
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