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Compound Detail

CHEMBL441738

AFAMELANOTIDE
💊 Approved Drug
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💊 Approved Drug
CCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(N)=O)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL441738
Name AFAMELANOTIDE
Phase Approved
Structure Type BOTH
InChI Key UAHFGYDRQSXQEB-LEBBXHLNSA-N
Therapeutic ✓ Yes

Known Names

(nle4,d-phe7)-.alpha.-msh Afamelanotida Afamelanotide CUV-1647 CUV1647 Melanotan Melanotan i Melanotan-1 Ndp-alpha-msh Scenesse
12
Targets
236
Activities
4
Assay Types
0
PK Parameters
20
Publications
10
Known Names
7
Indications
1
Mechanisms

Molecular Properties

1646.9
MW (Da)

Drug Information

Molecule Type Protein
First Approval 2014
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product First in Class
USAN Stem -tide
USAN Year 2017

Extended Properties

Molecular Formula C78H111N21O19
MW 1646.87

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Melanocortin receptor 1 agonist AGONIST Melanocyte-stimulating hormone receptor ✓ ✓

Indications

Protoporphyria, Erythropoietic Acne Vulgaris Ischemic Stroke Porphyria, Variegate Urticaria Vitiligo Xeroderma Pigmentosum

ATC Classification

D02BB02
afamelanotide
Level 1: DERMATOLOGICALS
Level 2: EMOLLIENTS AND PROTECTIVES

Activity Summary

EC50 172 meas. best 11.0
IC50 38 meas. best 9.82
Ki 24 meas. best 10.34
Kd 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Melanocyte-stimulating hormone receptor
CHEMBL4077
 EC50 11.0 10.4015 0.0 27
MCR
CHEMBL614332
 EC50 10.82 10.82 0.0 1
Melanocortin receptor 4
CHEMBL259
 EC50 10.77 9.2658 0.0 24
Melanocyte-stimulating hormone receptor
CHEMBL3795
 EC50 10.64 9.9525 0.0 8
Melanocortin receptor 5
CHEMBL4489
 EC50 10.52 9.7131 0.0 29
Melanocyte-stimulating hormone receptor
CHEMBL3795
 Ki 10.34 9.46 0.0 3
Melanocortin receptor 3
CHEMBL4774
 EC50 10.2 9.7676 0.1 29
Melanocortin receptor 4
CHEMBL3719
 EC50 10.01 9.4131 0.1 26
Melanocortin receptor 3
CHEMBL4023
 EC50 10.0 10.0 0.1 1
Melanocortin receptor 3
CHEMBL4644
 EC50 9.89 9.15 0.1 10
Melanocortin receptor 4
CHEMBL259
 IC50 9.82 8.9893 0.1 15
Melanocortin receptor 5
CHEMBL4608
 EC50 9.64 9.2114 0.2 7
Melanocortin receptor 4
CHEMBL259
 Ki 9.57 9.0356 0.3 16
Melanocyte-stimulating hormone receptor
CHEMBL4077
 IC50 9.54 9.525 0.3 2
Melanocortin receptor 5
CHEMBL4608
 Ki 9.32 8.66 0.5 2
Unchecked
CHEMBL612545
 EC50 9.3 9.3 0.5 1
Melanocyte-stimulating hormone receptor
CHEMBL3795
 IC50 9.29 9.29 0.5 2
Melanocortin receptor 3
CHEMBL4644
 Ki 9.17 9.14 0.7 2
Melanocortin receptor 5
CHEMBL4608
 IC50 9.07 8.902 0.9 5
Melanocortin receptor 4
CHEMBL3719
 IC50 8.96 8.7325 1.1 4
Melanocortin receptor 3
CHEMBL4644
 IC50 8.93 8.63 1.2 6
Melanocortin receptor 3
CHEMBL4774
 IC50 8.38 8.25 4.2 3
Adenosine deaminase
CHEMBL1910
 Ki 7.8 7.8 16.0 1
Melanocortin receptor 5
CHEMBL4489
 IC50 6.85 6.85 140.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Melanocyte-stimulating hormone receptor EC50 = 0.01 nM 11.0 Agonist activity at mouse melanocortin receptor 1 expressed in HEK293 cells asse... 31845801
Melanocyte-stimulating hormone receptor EC50 = 0.01 nM 11.0 Agonist activity at mouse MC1R by alphascreen cAMP assay 33062177
Melanocyte-stimulating hormone receptor EC50 = 0.01 nM 11.0 Agonist activity against mouse MC1R expressed in HEK293 cells assessed as increa... 37307241
Melanocyte-stimulating hormone receptor EC50 = 0.01 nM 11.0 Agonist activity at mouse MC1R expressed in HEK293 cells incubated for 2 hrs by ... 30035543
Melanocyte-stimulating hormone receptor EC50 = 0.014 nM 10.85 Agonistic activity against mouse MC1R 19635667
MCR EC50 = 0.015 nM 10.82 Effective concentration was measured against frog skin MCR cells at 10 e-4 10 e-... 9216831
Melanocyte-stimulating hormone receptor EC50 = 0.015 nM 10.82 Agonist activity at mouse MC1R expressed in HEK293 cells assessed as increase in... 28045525
Melanocortin receptor 4 EC50 = 0.017 nM 10.77 Effective concentration required for the biological activity against human Melan... 13678399
Melanocortin receptor 4 EC50 = 0.017 nM 10.77 Evaluated for agonist activity at cloned mammalian Melanocortin 4 receptor 7658432
Melanocyte-stimulating hormone receptor EC50 = 0.018 nM 10.74 Effective concentration for mouse Melanocortin-1 receptor 15828845
Melanocyte-stimulating hormone receptor EC50 = 0.018 nM 10.74 Agonist activity at mouse melanocortin 1 receptor expressed in HEK293 cells afte... 21306168
Melanocortin receptor 4 EC50 = 0.02 nM 10.7 Effective concentration of peptide at 50% maximal cAMP generation 12904077
Melanocyte-stimulating hormone receptor EC50 = 0.02 nM 10.7 Agonist activity at mouse MC1R expressed in HEK293 cells assessed as induction o... 28453292
Melanocyte-stimulating hormone receptor EC50 = 0.021 nM 10.68 Agonist activity at mouse melanocortin receptor 1 expressed in HEK293 cells asse... 28813605
Melanocyte-stimulating hormone receptor EC50 = 0.023 nM 10.64 Agonist activity at mouse MC1R expressed in HEK293 cells by beta-galactosidase a... 15615519
Melanocyte-stimulating hormone receptor EC50 = 0.023 nM 10.64 Evaluated for agonist activity at cloned mammalian human MSH1 receptor 7658432
Melanocyte-stimulating hormone receptor EC50 = 0.023 nM 10.64 Effective concentration required for the biological activity against human Melan... 13678399
Melanocyte-stimulating hormone receptor EC50 = 0.03 nM 10.52 Agonist activity at mouse MC1R expressed in HEK293 cells assessed as cAMP accumu... 26959173
Melanocyte-stimulating hormone receptor EC50 = 0.03 nM 10.52 Functional activity at the mouse melanocortin 1 receptor 11405661
Melanocortin receptor 5 EC50 = 0.03 nM 10.52 Agonist activity at mouse melanocortin 5 receptor expressed in HEK293 cells afte... 21306168

Literature References

PubMed DOI Target Context # Activities
16451057 10.1021/jm050780s Melanocortin receptor 4 30
28972753 10.1021/acs.jmedchem.7b00353 Melanocortin receptor 4 4
15771429 10.1021/jm049579s Melanocortin receptor 3 3
12904077 10.1021/jm030111j Melanocortin receptor 3 3
31845801 10.1021/acs.jmedchem.9b00860 Melanocortin receptor 4 3
15771429 10.1021/jm049579s Melanocortin receptor 5 3
15771429 10.1021/jm049579s Melanocortin receptor 4 3
12904077 10.1021/jm030111j Melanocortin receptor 4 3
11150170 10.1021/jm000211e Melanocortin receptor 4 3
12904077 10.1021/jm030111j Melanocortin receptor 5 3
11150170 10.1021/jm000211e Melanocortin receptor 3 3
11150170 10.1021/jm000211e Melanocortin receptor 5 3
24517312 10.1021/jm500064t Melanocortin receptor 4 3
15084118 10.1021/jm0303608 Melanocortin receptor 4 3
9276019 10.1021/jm970018t Melanocyte-stimulating hormone receptor 2
28849908 10.1021/acschembio.7b00481 Melanocortin receptor 4 2
9216831 10.1021/jm960840h Melanocyte-stimulating hormone receptor 2
9216831 10.1021/jm960840h Melanocortin receptor 3 2
9216831 10.1021/jm960840h Melanocortin receptor 4 2
12873485 10.1016/s0960-894x(03)00552-3 Melanocortin receptor 3 2

Data from ChEMBL 36 via Core Engine