Difelikefalin

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Difelikefalin
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Difelikefalin is an analgesic opioid peptide acting as a peripherally specific, highly selective agonist of the κ-opioid receptor (KOR). It acts as an analgesic by activating KORs on peripheral nerve terminals and KORs expressed by certain immune system cells. It may be useful in the prophylaxis and treatment of pain and inflammation associated with a variety of diseases and conditions. It is under development by Cara Therapeutics as an intravenous agent for the treatment of postoperative pain. It lacks the central side effects due to its peripheral selectivity. It is also being investigated for the treatment of pruritus (itching). It has completed phase II clinical trials for postoperative pain and has demonstrated significant and "robust" clinical efficacy, along with being safe and well-tolerated. It is also in phase II clinical trials for uremic pruritus in hemodialysis patients.

Category
Peptide Inhibitors
Catalog number
BAT-010193
CAS number
1024828-77-0
Molecular Formula
C36H53N7O6
Molecular Weight
679.8
Difelikefalin
Size Price Stock Quantity
100 mg $199 In stock
1 g $3149 In stock
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IUPAC Name
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
Synonyms
CR-845; MR-13A-9; MR-13A9
Appearance
Solid Powder
Purity
>98%
Density
1.2±0.1 g/cm3
Boiling Point
1005.5±65.0°C at 760 mmHg
Storage
Store at -20°C
Solubility
Soluble in DMSO
Application
Difelikefalin may be useful in the prophylaxis and treatment of pain and inflammation associated with a variety of diseases and conditions. It is used as an intravenous agent for the treatment of postoperative pain. It is also being investigated for the treatment of pruritus (itching).
InChI
InChI=1S/C36H53N7O6/c1-24(2)21-29(32(45)40-28(15-9-10-18-37)34(47)43-19-16-36(39,17-20-43)35(48)49)42-33(46)30(23-26-13-7-4-8-14-26)41-31(44)27(38)22-25-11-5-3-6-12-25/h3-8,11-14,24,27-30H,9-10,15-23,37-39H2,1-2H3,(H,40,45)(H,41,44)(H,42,46)(H,48,49)/t27-
InChI Key
FWMNVWWHGCHHJJ-SKKKGAJSSA-N
Canonical SMILES
CC(C)CC(C(=O)NC(CCCCN)C(=O)N1CCC(CC1)(C(=O)O)N)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC3=CC=CC=C3)N
1.Targeting Itch with Ligands Selective for κ Opioid Receptors.
Cowan A;Kehner GB;Inan S Handb Exp Pharmacol. 2015;226:291-314. doi: 10.1007/978-3-662-44605-8_16.
Several chemically diverse pruritogens, including bombesin, compound 48/80, norbinaltorphimine, and 5'-GNTI, cause rodents to scratch excessively in a stable, uniform manner and consequently provide convenient animal models of itch against which potential antipruritics may be evaluated, structure-activity relationships established, and the nature of spontaneous, repetitive behavior itself analyzed. Decreasing the number of scratching bouts in these apparently simple models has been the requisite first step in the progress of kappa opioid agonists such as nalbuphine, asimadoline, and CR845 toward clinical testing as antipruritics. Nalfurafine is the prime example of a kappa agonist spanning the developmental divide between scratching mice models and commercialization within 10 years. Patients undergoing hemodialysis and suffering from the itching associated with uremic pruritus, and potentially those inflicted with atopic dermatitis, are the beneficiaries.
2.The opioid crisis: a 21st century pain.
Walker G Drugs Today (Barc). 2018 Apr;54(4):283-286. doi: 10.1358/dot.2018.54.4.2812620.
The opioid pain market is a lucrative one, but is experiencing significant challenges in the U.S. as the country grapples with prescription opioid addiction, overdose and fatalities. The situation has been declared a national Public Health Emergency and the Food and Drug Administration (FDA) has introduced several measures intended to reduce opioid abuse. The development of abuse-deterrent prescription opioids is one such measure, but although abuse-deterrent formulations of opioids reduce drug liking and abuse, concerns have been highlighted by an Institute of Clinical and Economic Review (ICER) report regarding the insufficiency of currently available data to determine the effects of these formulations at the population level. However, the low abuse liability but effective analgesic efficacy reported for drugs such as NKTR-181 and difelikefalin highlight the potential of novel abuse-deterrent opioids.

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