Afamelanotide

Afamelanotide

Clinical data
Pronunciation	i/ˌæfəmɛˈlænoʊtaɪd/
Trade names	Scenesse
AHFS/Drugs.com	UK Drug Information
Routes of administration	S.C.; I.M.; I.V.; subcutaneous implant; intranasal
ATC code	D02BB02 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Biological half-life	30 minutes
Identifiers
IUPAC name N-acetyl-L-seryl-L-tyrosyl-L-seryl-L-norleucyl-L-α-glutamyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide
Synonyms	Melanotan; Melanotan-1; Melanotan I; CUV1647; EPT1647; NDP-MSH; NDP-α-MSH; [Nle4,D-Phe7]α-MSH
CAS Number	75921-69-6 N
PubChem CID	16154396
ChemSpider	17310725 Y
UNII	QW68W3J66U
KEGG	D10511 N
ChEMBL	CHEMBL441738 Y
Chemical and physical data
Formula	C78H111N21O19
Molar mass	1646.845 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1[C@H](C(=O)N[C@H](C(=O)N)C(C)C)CCC1)CCCCN)Cc3c2ccccc2[nH]c3)CCCNC(=[N@H])N)Cc4ccccc4)Cc5ncnc5)CCC(=O)O)CCCC)CO)Cc6ccc(O)cc6)[C@@H](NC(=O)C)CO
InChI InChI=1S/C78H111N21O19/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/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)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-/m0/s1 Y Key:UAHFGYDRQSXQEB-LEBBXHLNSA-N Y
NY (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. It is administered as an implant that is placed under the skin; 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.

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. 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 is thought to cause skin to darken by binding to the melanocortin 1 receptor which in turn drives melanogenesis.