setmelanotide   Click here for help

GtoPdb Ligand ID: 9272

Synonyms: BIM-22493 | Imcivree® | IRC-022493 | RM-493
Approved drug
setmelanotide is an approved drug (FDA (2020), EMA (2021))
Compound class: Peptide or derivative
Comment: Setmelanotide is an agonist of melanocortin receptors, with approximately 20-fold selectivity for the melanocortin 4 receptor subtype [5]. Chemically it is an eight-amino-acid cyclic peptide, that is able to cross the blood-brain barrier when administered peripherally. Setmelanotide offers anti-obesity potential.
The INN record documents the sequence as N2-acetyl-L-arginyl-L-cysteinyl-D-alanyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-L-cysteinamide, cyclic (2-8)-disulfide.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NC(=NCCCC(C(=O)NC1CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)C)Cc1[nH]cnc1)Cc1ccccc1)CCCN=C(N)N)Cc1c[nH]c2c1cccc2)C(=O)N)NC(=O)C)N
Isomeric SMILES NC(=NCCC[C@@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)C)Cc1[nH]cnc1)Cc1ccccc1)CCCN=C(N)N)Cc1c[nH]c2c1cccc2)C(=O)N)NC(=O)C)N
InChI InChI=1S/C49H68N18O9S2/c1-26-41(70)63-37(20-30-22-55-25-59-30)46(75)64-35(18-28-10-4-3-5-11-28)44(73)62-34(15-9-17-57-49(53)54)43(72)65-36(19-29-21-58-32-13-7-6-12-31(29)32)45(74)66-38(40(50)69)23-77-78-24-39(47(76)60-26)67-42(71)33(61-27(2)68)14-8-16-56-48(51)52/h3-7,10-13,21-22,25-26,33-39,58H,8-9,14-20,23-24H2,1-2H3,(H2,50,69)(H,55,59)(H,60,76)(H,61,68)(H,62,73)(H,63,70)(H,64,75)(H,65,72)(H,66,74)(H,67,71)(H4,51,52,56)(H4,53,54,57)/t26-,33+,34+,35-,36+,37+,38+,39+/m1/s1
InChI Key HDHDTKMUACZDAA-PHNIDTBTSA-N
Bioactivity Comments
EC50 values for cAMP production in vitro vs. human melanocortin receptors are MC4R (0.27mM), MC3R (5.3nM), MC1R (5.8nM), and rat MC4R (0.28nM) [5].
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
MC4 receptor Hs Agonist Agonist 8.7 pKi - 2,5
⤷ pKi 8.7 (Ki 2.1x10-9 M) [2,5]
MC4 receptor Rn Agonist Agonist 8.6 pKi - 5
⤷ pKi 8.6 (Ki 2.7x10-9 M) [5]
MC1 receptor Hs Agonist Agonist 8.4 pKi - 5
⤷ pKi 8.4 (Ki 3.9x10-9 M) [5]
MC3 receptor Hs Agonist Agonist 8.0 pKi - 5
⤷ pKi 8.0 (Ki 1x10-8 M) [5]
MC5 receptor Hs Agonist Agonist 6.4 pKi - 5
⤷ pKi 6.4 (Ki 4.3x10-7 M) [5]
Ligand mentioned in the following text fields
Melanocortin receptors overview