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Afamelanotide information


Afamelanotide
Clinical data
Pronunciation/ˌæfəmɛˈlæntd/
Trade namesScenesse
Other names[Nle4,D-Phe7]α-MSH; NDP-α-MSH; NDP-MSH; Melanotan; Melanotan-1; Melanotan I; EPT1647; CUV1647;
AHFS/Drugs.comMonograph
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[1]
  • EU: Rx-only[2]
Pharmacokinetic data
Elimination half-life30 minutes[3]
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 ☒N
PubChem CID
  • 16154396
IUPHAR/BPS
  • 1324
DrugBank
  • DB04931
ChemSpider
  • 17310725 checkY
UNII
  • QW68W3J66U
KEGG
  • D10511 ☒N
  • as salt: D11334 ☒N
ChEBI
  • CHEBI:136034
ChEMBL
  • ChEMBL441738 checkY
CompTox Dashboard (EPA)
  • DTXSID40226843 Edit this at Wikidata
Chemical and physical data
FormulaC78H111N21O19
Molar mass1646.874 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 checkY
  • Key:UAHFGYDRQSXQEB-LEBBXHLNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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-R) 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]

  1. ^ 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.
  2. ^ a b Cite error: The named reference Scenesse EPAR was invoked but never defined (see the help page).
  3. ^ a b Cite error: The named reference EMA2017 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference FDA Snapshot was invoked but never defined (see the help page).
  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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Afamelanotide

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nausea and vomiting. As a tanning agent, melanotan I (now known as afamelanotide) was licensed by Competitive Technologies, a technology transfer company...

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and racist antics in nearly every episode. As of July 2013[update], afamelanotide is in phase II and III clinical trials for vitiligo and other skin diseases...

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Retrieved 2020-09-24. "Scenesse (afamelanotide) for adults with a history of phototoxic reactions from EPP". SCENESSE® (Afamelanotide). Retrieved 2020-09-24. Kraemer...

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Melanocortin receptor

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peptide and agouti-related peptide, and activated by synthetic (i.e. afamelanotide) and endogenous agonist melanocyte-stimulating hormones. Several selective...

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other peptide analogues of the same family as bremelanotide include afamelanotide (NDP-α-MSH), modimelanotide, and setmelanotide. Studies in the early...

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Melanotan

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Melanotan may refer to one of two separate peptides: Afamelanotide, originally developed under the names "Melanotan", "Melanotan-1", or "Melanotan I"...

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Sunless tanning

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several analogs, including afamelanotide, then called melanotan-I. In the European Union and United States, afamelanotide is indicated for the prevention...

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Melanocortin

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approved for chronic weight management in patients with genetic obesity. Afamelanotide (Scenesse) is an MC1R agonist approved for patients with erythropoietic...

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Erythropoietic protoporphyria

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Unless there is liver failure, it is not a life-threatening disease. Afamelanotide, developed by Australian-based Clinuvel Pharmaceuticals, was approved...

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ATC code D02

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D02BA01 Aminobenzoic acid D02BA02 Octinoxate D02BB01 Betacarotene D02BB02 Afamelanotide "ATC (Anatomical Therapeutic Chemical Classification System) – Synopsis"...

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Caffeine

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should suggest likely mechanisms of this interaction.[citation needed] Afamelanotide Agouti-related peptide Melanocortin Melanotan II GRCh38: Ensembl release...

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Dupilumab

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Porphyria

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although long-term results are not yet available. In December 2014, afamelanotide received authorization from the European Commission as a treatment for...

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Ivermectin

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Management of hair loss

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Melanocortin 4 receptor

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erectile dysfunction. The non-selective melanocortin receptor agonist afamelanotide (NDP-α-MSH) has been found to induce brain-derived neurotrophic factor...

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Seborrhoeic dermatitis

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nonselective peptide full agonist ACTH - nonselective peptide full agonist Afamelanotide - nonselective peptide full agonist BMS-470,539 - selective small-molecule...

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Setmelanotide

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