afamelanotide

Also known as α-NDP-MSH, [Nle4,dPhe7]α-MSH, NDP-MSH, MT-I, melanotan 1, melanotan I

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. It is a melanocortin 1 receptor (MC1 receptor) agonist and a synthetic peptide and analogue of α-melanocyte stimulating hormone. It is administered as subcutaneous implant.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 477364562
Drug.image: Melanotan.png
Drug.image_class: skin-invert-image
Drug.tradename: Scenesse
Drug.DailyMedID: Afamelanotide
Drug.pregnancy_AU: B1
Drug.routes_of_administration: Subcutaneous
Drug.ATC_prefix: D02
Drug.ATC_suffix: BB02
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only
Drug.elimination_half life: 30 minutes
Drug.index2_label: as salt
Drug.CAS_number: 75921-69-6

via Wikipedia infobox

Chemical data

Formula: C78H111N21O19
Molecular weight: 1646.8 g/mol
IUPAC 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-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
SMILES: CCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CN=CN1)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
InChIKey: UAHFGYDRQSXQEB-LEBBXHLNSA-N
XLogP: -3.5
Polar surface area: 643 Å²
H-bond donors: 23
H-bond acceptors: 22
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 2014
Admin. routes: parenteral
Indications: Vitiligo, urticaria, acne, Ischemic stroke

via ChEMBL · EBI

Research

117 papers

Afamelanotide.2012
Afamelanotide in protoporphyria and other skin diseases: a review.Postepy dermatologii i alergologii · 2024
PMID 402581052023
Afamelanotide for prevention of phototoxicity in erythropoietic protoporphyria.Expert review of clinical pharmacology · 2021
Afamelanotide: An Orphan Drug with Potential for Broad Dermatologic Applications.Journal of drugs in dermatology : JDD · 2021

via PubMed

Wikidata facts

Mass: 1645.83651

Show 3 more facts

chemical formula: C₇₈H₁₁₁N₂₁O₁₉
canonical 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
isomeric SMILES: CCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CN=CN1)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

Sources (2)

via Wikidata · CC0

~6 min read

Encyclopedic overview

8 sections

Contents

Medical uses
Adverse effects
Pharmacology
Chemistry
History
Society and culture
Usage in general public
References

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

Excerpted from Wikipedia’s “afamelanotide” article, available under the CC BY-SA 4.0 licence.

Available in 12 languages

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