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152657-84-6,MFCD09837714
Catalog No.:AA00ABLQ

152657-84-6 | NALFURAFINE

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00ABLQ
Chemical Name:
NALFURAFINE
CAS Number:
152657-84-6
Molecular Formula:
C28H32N2O5
Molecular Weight:
476.5641
MDL Number:
MFCD09837714
SMILES:
CN([C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O)C(=O)/C=C/c1ccoc1
Properties
Computed Properties
 
Complexity:
893  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
35  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
1  

Literature

Title: Targeting Itch with Ligands Selective for κ Opioid Receptors.

Journal: Handbook of experimental pharmacology 20150101

Title: In vitro and in vivo pharmacological characterization of the main metabolites of nalfurafine hydrochloride.

Journal: European journal of pharmacology 20121115

Title: Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 2: synthesis of decahydro(iminoethano)phenanthrene derivatives and their pharmacologies.

Journal: Bioorganic & medicinal chemistry letters 20120801

Title: Identification of human cytochrome P450 enzymes involved in the metabolism of a novel к-opioid receptor agonist, nalfurafine hydrochloride.

Journal: Biopharmaceutics & drug disposition 20120701

Title: Design and synthesis of novel opioid ligands with an azabicyclo[2.2.2]octane skeleton and their pharmacologies.

Journal: Bioorganic & medicinal chemistry letters 20120415

Title: Essential structure of opioid κ receptor agonist nalfurafine for binding to κ receptor 1: synthesis of decahydroisoquinoline derivatives and their pharmacologies.

Journal: Chemical & pharmaceutical bulletin 20120101

Title: Investigation of gastrin-releasing peptide as a mediator for 5'-guanidinonaltrindole-induced compulsive scratching in mice.

Journal: Peptides 20110201

Title: Synthesis of 6,14-epoxymorphinan derivatives and their pharmacologies.

Journal: Bioorganic & medicinal chemistry 20110201

Title: Opioids in preclinical and clinical trials.

Journal: Topics in current chemistry 20110101

Title: Synthesis of pyrrolomorphinan derivatives as kappa opioid agonists.

Journal: Bioorganic & medicinal chemistry letters 20100901

Title: Drug design and synthesis of a novel kappa opioid receptor agonist with an oxabicyclo[2.2.2]octane skeleton and its pharmacology.

Journal: Bioorganic & medicinal chemistry letters 20100101

Title: TRK-820, a selective kappa opioid receptor agonist, could effectively ameliorate L-DOPA-induced dyskinesia symptoms in a rat model of Parkinson's disease.

Journal: European journal of pharmacology 20091012

Title: Nalfurafine prevents 5'-guanidinonaltrindole- and compound 48/80-induced spinal c-fos expression and attenuates 5'-guanidinonaltrindole-elicited scratching behavior in mice.

Journal: Neuroscience 20090929

Title: Synthesis of a new opioid ligand having the oxabicyclo[3.2.1]octane skeleton using a new rearrangement reaction.

Journal: Bioorganic & medicinal chemistry letters 20090501

Title: Effects of TRK-820, a selective kappa opioid receptor agonist, on rat schizophrenia models.

Journal: European journal of pharmacology 20090315

Title: Comparison of the diuretic effects of chemically diverse kappa opioid agonists in rats: nalfurafine, U50,488H, and salvinorin A.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20090301

Title: Effects of atypical kappa-opioid receptor agonists on intrathecal morphine-induced itch and analgesia in primates.

Journal: The Journal of pharmacology and experimental therapeutics 20090101

Title: The kappa-opiate receptor impacts the pathophysiology and behavior of substance use.

Journal: The American journal on addictions 20090101

Title: [Uremic pruritus: an unresolved challenge].

Journal: Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia 20090101

Title: Design, synthesis, and structure-activity relationship of novel opioid kappa-agonists.

Journal: Bioorganic & medicinal chemistry 20081015

Title: [Effect of TRK-820, a selective kappa opioid receptor agonist, on scratching behavior in an animal model of atopic dermatitis].

Journal: Nihon shinkei seishin yakurigaku zasshi = Japanese journal of psychopharmacology 20080401

Title: Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers.

Journal: Bioorganic & medicinal chemistry 20080201

Title: Nalfurafine, the kappa opioid agonist, inhibits icilin-induced wet-dog shakes in rats and antagonizes glutamate release in the dorsal striatum.

Journal: Neuropharmacology 20070301

Title: Specific down-regulation of spinal mu-opioid receptor and reduced analgesic effects of morphine in mice with postherpetic pain.

Journal: European journal of pharmacology 20061121

Title: Mu and kappa opioid receptor agonists antagonize icilin-induced wet-dog shaking in rats.

Journal: European journal of pharmacology 20061010

Title: Nalfurafine, a kappa opioid receptor agonist, inhibits scratching behavior secondary to cholestasis induced by chronic ethynylestradiol injections in rats.

Journal: Pharmacology, biochemistry, and behavior 20060901

Title: Generalization of NMDA-receptor antagonists to the discriminative stimulus effects of kappa-opioid receptor agonists U-50,488H, but not TRK-820 in rats.

Journal: Journal of pharmacological sciences 20060201

Title: Spontaneous scratching behavior in MRL/lpr mice, a possible model for pruritus in autoimmune diseases, and antipruritic activity of a novel kappa-opioid receptor agonist nalfurafine hydrochloride.

Journal: European journal of pharmacology 20050822

Title: Comparison of pharmacological activities of three distinct kappa ligands (Salvinorin A, TRK-820 and 3FLB) on kappa opioid receptors in vitro and their antipruritic and antinociceptive activities in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 20050101

Title: Inhibitory effects of TRK-820 on systemic skin scratching induced by morphine in rhesus monkeys.

Journal: Life sciences 20041029

Title: Differential properties between TRK-820 and U-50,488H on the discriminative stimulus effects in rats.

Journal: Life sciences 20041001

Title: Possible pharmacotherapy of the opioid kappa receptor agonist for drug dependence.

Journal: Annals of the New York Academy of Sciences 20041001

Title: Syntheses of 10-oxo, 10 alpha-hydroxy, and 10 beta-hydroxy derivatives of a potent kappa-opioid receptor agonist, TRK-820.

Journal: Chemical & pharmaceutical bulletin 20040601

Title: Suppression of acute herpetic pain-related responses by the kappa-opioid receptor agonist (-)-17-cyclopropylmethyl-3,14beta-dihydroxy-4,5alpha-epoxy-beta-[n-methyl-3-trans-3-(3-furyl) acrylamido] morphinan hydrochloride (TRK-820) in mice.

Journal: The Journal of pharmacology and experimental therapeutics 20040401

Title: Region-dependent G-protein activation by kappa-opioid receptor agonists in the mouse brain.

Journal: Neuroscience letters 20040212

Title: Effect of repeated administration of TRK-820, a kappa-opioid receptor agonist, on tolerance to its antinociceptive and sedative actions.

Journal: Brain research 20040109

Title: Involvement of central mu-opioid system in the scratching behavior in mice, and the suppression of it by the activation of kappa-opioid system.

Journal: European journal of pharmacology 20030905

Title: Blockade of mu-opioid receptor-mediated G-protein activation and antinociception by TRK-820 in mice.

Journal: European journal of pharmacology 20030207

Title: Modulation of kappa-opioidergic systems on mecamylamine-precipitated nicotine-withdrawal aversion in rats.

Journal: Neuroscience letters 20020426

Title: Effects of a newly synthesized kappa-opioid receptor agonist, TRK-820, on the discriminative stimulus and rewarding effects of cocaine in rats.

Journal: Psychopharmacology 20020401

Title: Antipruritic activity of the kappa-opioid receptor agonist, TRK-820.

Journal: European journal of pharmacology 20020125

Title: The novel kappa-opioid receptor agonist TRK-820 suppresses the rewarding and locomotor-enhancing effects of morphine in mice.

Journal: Life sciences 20010302

Title: TRK-820, a selective kappa-opioid agonist, produces potent antinociception in cynomolgus monkeys.

Journal: Japanese journal of pharmacology 20010301

Title: Kaski SW, et al. Preclinical Testing of Nalfurafine as an Opioid-sparing Adjuvant that Potentiates Analgesia by the Mu Opioid Receptor-targeting Agonist Morphine.J Pharmacol Exp Ther. 2019 Nov;371(2):487-499.

Title: Endoh T, et al. Potent antinociceptive effects of TRK-820, a novel kappa-opioid receptor agonist.Life Sci. 1999;65(16):1685-94.

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