bremelanotide   Click here for help

GtoPdb Ligand ID: 10408

Synonyms: PT-141 | PT141 | Vyleesi®
Approved drug
bremelanotide is an approved drug (FDA (2019))
Comment: Bremelanotide is a stabilised, cyclic derivative of αMSH. Although it exhibits little selectivity across the melanocortin receptor family (with the exception of MC2, the ACTH receptor), bremelanotide's ability to increase female sexual arousal/desire is attributed primarily to agonist activity at the MC3 and MC4 receptors [2].
HELM annotation is PEPTIDE1{[ac].[Nle].D.H.[dF].R.W.K}$PEPTIDE1,PEPTIDE1,3:R3-8:R3$$$.
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES CCCCC(C(=O)NC1CC(=O)NCCCCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)Cc1[nH]cnc1)Cc1ccccc1)CCCN=C(N)N)Cc1c[nH]c2c1cccc2)C(=O)O)NC(=O)C
Isomeric SMILES CCCC[C@@H](C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)Cc1[nH]cnc1)Cc1ccccc1)CCCN=C(N)N)Cc1c[nH]c2c1cccc2)C(=O)O)NC(=O)C
InChI InChI=1S/C50H68N14O10/c1-3-4-16-35(58-29(2)65)43(67)64-41-25-42(66)54-20-11-10-18-37(49(73)74)60-46(70)39(23-31-26-56-34-17-9-8-15-33(31)34)62-44(68)36(19-12-21-55-50(51)52)59-45(69)38(22-30-13-6-5-7-14-30)61-47(71)40(63-48(41)72)24-32-27-53-28-57-32/h5-9,13-15,17,26-28,35-41,56H,3-4,10-12,16,18-25H2,1-2H3,(H,53,57)(H,54,66)(H,58,65)(H,59,69)(H,60,70)(H,61,71)(H,62,68)(H,63,72)(H,64,67)(H,73,74)(H4,51,52,55)/t35-,36-,37-,38+,39-,40-,41-/m0/s1
InChI Key FFHBJDQSGDNCIV-MFVUMRCOSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
MC4 receptor Hs Agonist Agonist 9.6 pKi - 1
pKi 9.6 (Ki 2.5x10-10 M) [1]
Description: Inhibition of 125I-NDP-αMSH binding to membranes from BHK570 cells stably expressing human MC4 receptor.
MC1 receptor Hs Agonist Agonist 8.2 pKi - 1
pKi 8.2 (Ki 6.4x10-9 M) [1]
Description: Inhibition of 125I-NDP-αMSH binding to membranes from BHK570 cells stably expressing human MC1 receptor.
MC5 receptor Hs Agonist Agonist 7.8 pKi - 1
pKi 7.8 (Ki 1.7x10-8 M) [1]
Description: Inhibition of 125I-NDP-αMSH binding to membranes from BHK570 cells stably expressing human MC5 receptor.
MC3 receptor Hs Agonist Agonist 7.3 pKi - 1
pKi 7.3 (Ki 5.3x10-8 M) [1]
Description: Inhibition of 125I-NDP-αMSH binding to membranes from BHK570 cells stably expressing human MC3 receptor.