Compound: Difelikefalin
SMILES: O=C(O)C1(N)CCN(C(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](N)Cc2ccccc2)Cc3ccccc3)CC(C)C)CCCCN)CC1
InChIKey: FWMNVWWHGCHHJJ-SKKKGAJSSA-N
Synonyms: Difelikefalin, 1024828-77-0, CR845, Korsuva, CR-845, MR13A9, difelicefalina, difelikefaline, FE202845, NA1U919MRO, FE-202845, MR-13A9, DTXSID401032896, 4-amino-1-[(2R)-6-amino-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid, 4-Piperidinecarboxylic acid, N1-(D-phenylalanyl-D-phenylalanyl-D-leucyl-D-lysyl)-4-amino-, 4-Piperidinecarboxylic acid, 4-amino-1-((2R)-6-amino-2-(((2R)-2-(((2R)-2-(((2R)-2-amino-1-oxo-3-phenylpropyl)amino)-1-oxo-3-phenylpropyl)amino)-4-methyl-1-oxopentyl)amino)-1-oxohexyl)-, 4-amino-1-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-amino-3-phenylpropanamido]-3-phenylpropanamido]-4-methylpentanamido]hexanoyl]piperidine-4-carboxylic acid, difelikefalinum, 4-amino-1-((2R)-6-amino-2-(((2R)-2-(((2R)-2-(((2R)-2-amino-3-phenylpropanoyl)amino)-3-phenylpropanoyl)amino)-4-methylpentanoyl)amino)hexanoyl)piperidine-4-carboxylic acid, 4-amino-1-((2R)-6-amino-2-((2R)-2-((2R)-2-((2R)-2-amino-3-phenylpropanamido)-3-phenylpropanamido)-4-methylpentanamido)hexanoyl)piperidine-4-carboxylic acid, RefChem:57567, DTXCID701517924, Difelikefalin (CR845), Difelikefalin [INN], 1-(D-phenylalanyl-D-phenylalanyl-D-leucyl-D-lysyl)-4-aminopiperidine-4-carboxylic acid, 4-Amino-1-((R)-6-amino-2-((R)-2-((R)-2-((R)-2-amino-3-phenylpropanamido)-3-phenylpropanamido)-4-methylpentanamido)hexanoyl)piperidine-4-carboxylic acid, UNII-NA1U919MRO, Kapruvia, Difelikefalin TFA, CR 845, 1024828-77-0 (free base), Difelikefalin (USAN/INN), Difelikefalin [USAN:INN], DIFELIKEFALIN [USAN], SEQ ID NO: 2, orb611270, DIFELIKEFALIN [WHO-DD], GTPL9044, CHEMBL3989915, SCHEMBL10316464, BDBM235785, DIFELIKEFALIN ACETATE [JAN], EX-A5855, EBC-47107, AKOS040756421, AT30197, DB11938, BD177570, BP-50420, DA-52529, HY-17609, MS-31091, CR-845; FE-202845, CS-0014687, NS00072889, D11111, US9359399, 2, EN300-7445060, Q21098992, D-Phe-D-Phe-D-Leu-D-Lys-[gamma-(4-N-piperidinyl)amino carboxylic acid], 4-Piperidinecarboylic acid, 4-amino-1-(D-phenylalanyl-D-phenylalanyl-D-leucyl-D-lysyl)-, 4-AMINO-1-(D-PHENYLALANYL-D-PHENYLALANYL-D-LEUCYL-D-LYSYL)PIPERIDINE-4-CARBOXYLIC ACID, Difelikefalin; 4-Piperidinecarboxylic acid, N1-(D-phenylalanyl-D-phenylalanyl-D-leucyl-D-lysyl)-4-amino-; N1-(D-Phenylalanyl-D-phenylalanyl-D-leucyl-D-lysyl)-4-amino-4-piperidinecarboxylic acid; CR 845; Difelikefalin, N-((2R)-1-(((2R)-1-(((2R)-6-Amino-1-(4-amino-4-carboxy-1-piperidinyl)-1-oxo-2-hexanyl)amino)-4-methyl-1-oxo-2-pentanyl)amino)-1-oxo-3-phenyl-2-propanyl)-D-phenylalaninamide
Theoretical properties:
molecular_formula: C36H53N7O6
molecular_weight: 679.8 g/mol
exact_mass: 679.40573244 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 18
heavy_atom_count: 49
topological_polar_surface_area: 223 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Soluble
Descriptions:
chembl: DIFELIKEFALIN is a protein listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Difelikefalin, sold under the brand name Korsuva, is an opioid peptide used for the treatment of moderate to severe itch. It acts as a peripherally-restricted, highly selective agonist of the κ-opioid receptor (KOR).
Difelikefalin acts as an analgesic by activating KORs on peripheral nerve terminals and KORs expressed by certain immune system cells. Activation of KORs on peripheral nerve terminals results in the inhibition of ion channels responsible for afferent nerve activity, causing reduced transmission of pain signals, while activation of KORs expressed by immune system cells results in reduced release of proinflammatory, nerve-sensitizing mediators (e.g., prostaglandins).
Difelikefalin was approved for medical use in the United States in August 2021. The U.S. Food and Drug Administration considers it to be a first-in-class medication.