NALFURAFINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H32N2O5
Molecular Weight	476.5641
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(CC6CC6)CC[C@@]14[C@@]5(O)CC[C@H]2N(C)C(=O)\C=C\C7=COC=C7)=CC=C3O

InChI

InChIKey=XGZZHZMWIXFATA-UEZBDDGYSA-N

InChI=1S/C28H32N2O5/c1-29(23(32)7-4-18-9-13-34-16-18)20-8-10-28(33)22-14-19-5-6-21(31)25-24(19)27(28,26(20)35-25)11-12-30(22)15-17-2-3-17/h4-7,9,13,16-17,20,22,26,31,33H,2-3,8,10-12,14-15H2,1H3/b7-4+/t20-,22-,26+,27+,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H32N2O5
Molecular Weight	476.5641
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26005355 | https://www.ncbi.nlm.nih.gov/pubmed/19584962 | http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/human/002683/WC500162688.pdf

Nalfurafine, an opioid κ-selective agonist, has been officially approved for resistant pruritus in HD patients on the basis of a well-evidenced clinical trial in Japan. Nalfurafine hydrochloride is a potent and selective agonist for mouse, rat, guinea pig, and human κ-opioid receptors without significant activity on µ- and δ-opioid receptors. Nalfurafine hydrochloride (2.5 and 5 ug/day) has been proven to be safe and effective for the treatment of HD patients with uremic pruritus resistant to antihistamines.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/human/002683/WC500162688.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/15383632	Agonist 2678		25.0 pM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pruritus in hemodialysis patients 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26005355 https://www.ncbi.nlm.nih.gov/pubmed/19584962	Primary		Approved 8429	REMITCH Approved Use Improvement of pruritus in hemodialysis patients (only for cases resistant to conventional treatments) Launch Date 1.23249597E12

PubMed

Title	Date	PubMed
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.	2005 Jan	15383632
Nalfurafine, a kappa opioid receptor agonist, inhibits scratching behavior secondary to cholestasis induced by chronic ethynylestradiol injections in rats.	2006 Sep	16919318
TRK-820, a selective kappa opioid receptor agonist, could effectively ameliorate L-DOPA-induced dyskinesia symptoms in a rat model of Parkinson's disease.	2009 Oct 12	19686730
Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 2: synthesis of decahydro(iminoethano)phenanthrene derivatives and their pharmacologies.	2012 Aug 1	22742909

Patents

Sample Use Guides

In Vivo Use Guide

The usual oral dosage for adults is 2.5 ug of nalfurafine hydrochloride, once a day, after supper or before sleep. The dosage may be adjusted according to symptoms provided that it does not exceed 5 ug once a day.

Route of Administration: Oral

In Vitro Use Guide

Nalfurafine hydrochloride inhibited the electrically-induced contraction of mouse vas deferens with the IC50 of 0.080 nmol/L and 0.12 nmol/L in two independent experiments in vitro.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:14:10 UTC 2023` Edited by `admin` on `Fri Dec 15 17:14:10 UTC 2023`
Record UNII	XC41AVD567
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NALFURAFINE

Official Name

English

nalfurafine [INN]

Common Name

English

NALFURAFINE [MI]

Common Name

English

2-PROPENAMIDE, N-((5.ALPHA.,6.BETA.)-17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-3,14-DIHYDROXYMORPHINAN-6-YL)-3-(3-FURANYL)-N-METHYL-, (2E)-

Systematic Name

English

Nalfurafine [WHO-DD]

Common Name

English

MT-9938

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67413