Afamelanotide

Afamelanotide
Clinical data
Pronunciation	/ˌæfəmɛˈlænoʊtaɪd/ ⓘ
Trade names	Scenesse
Other names	[Nle4,D-Phe7]α-MSH; NDP-α-MSH; NDP-MSH; Melanotan; Melanotan-1; Melanotan I; EPT1647; CUV1647;
AHFS/Drugs.com	Monograph
License data	US DailyMed: Afamelanotide;
Pregnancy; category	AU: B1;
Routes of; administration	Subcutaneous
ATC code	D02BB02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Elimination 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;
CAS Number	75921-69-6 ;
PubChem CID	16154396;
IUPHAR/BPS	1324;
DrugBank	DB04931;
ChemSpider	17310725 ;
UNII	QW68W3J66U;
KEGG	D10511 ; as salt: D11334 ;
ChEBI	CHEBI:136034;
ChEMBL	ChEMBL441738 ;
CompTox Dashboard (EPA)	DTXSID40226843 ;
Chemical and physical data
Formula	C78H111N21O19
Molar mass	1646.874 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCC(C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CN=CN1)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;
	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 ; Key:UAHFGYDRQSXQEB-LEBBXHLNSA-N ;
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Afamelanotide, sold under the brand name Scenesse, is a medication used to prevent phototoxicity and to reduce pain from light exposure for people with erythropoietic protoporphyria.^[1]^[2]^[4] It is a melanocortin 1 receptor (MC₁ receptor) agonist^[1] and a synthetic peptide and analogue of α-melanocyte stimulating hormone.^[1] It is administered as subcutaneous implant.^[3]

The US Food and Drug Administration (FDA) considers it to be a first-in-class medication.^[5]

^ ^a ^b ^c ^d "Scenesse- afamelanotide implant". DailyMed. U.S. National Library of Medicine. 15 May 2023. Archived from the original on 25 July 2022. Retrieved 15 June 2023.
^ ^a ^b Cite error: The named reference Scenesse EPAR was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference EMA2017 was invoked but never defined (see the help page).
^ "Drug Trials Snapshots: Scenesse". U.S. Food and Drug Administration (FDA). 8 October 2019. Archived from the original on 13 August 2020. Retrieved 26 January 2020. This article incorporates text from this source, which is in the public domain.
^ "New Drug Therapy Approvals 2019". U.S. Food and Drug Administration. 31 December 2019. Archived from the original on 16 September 2020. Retrieved 15 September 2020.

[Scenesse_FDA_label-1] "Scenesse- afamelanotide implant". DailyMed. U.S. National Library of Medicine. 15 May 2023. Archived from the original on 25 July 2022. Retrieved 15 June 2023.

[Scenesse_EPAR-2] Cite error: The named reference Scenesse EPAR was invoked but never defined (see the help page).

[EMA2017-3] Cite error: The named reference EMA2017 was invoked but never defined (see the help page).

[FDA_Snapshot-4] "Drug Trials Snapshots: Scenesse". U.S. Food and Drug Administration (FDA). 8 October 2019. Archived from the original on 13 August 2020. Retrieved 26 January 2020. This article incorporates text from this source, which is in the public domain.

[5] "New Drug Therapy Approvals 2019". U.S. Food and Drug Administration. 31 December 2019. Archived from the original on 16 September 2020. Retrieved 15 September 2020.

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