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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H32N2O5.ClH
Molecular Weight 513.025
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NALFURAFINE HYDROCHLORIDE

SMILES

Cl.[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=DJSFYNINGIMKAG-FQJQBBMWSA-N
InChI=1S/C28H32N2O5.ClH/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;1H/b7-4+;/t20-,22-,26+,27+,28-;/m1./s1

HIDE SMILES / InChI

Description

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 25.0 pM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
REMITCH

Approved Use

Improvement of pruritus in hemodialysis patients (only for cases resistant to conventional treatments)

Launch Date

2009
PubMed

PubMed

TitleDatePubMed
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
Nalfurafine, a kappa opioid receptor agonist, inhibits scratching behavior secondary to cholestasis induced by chronic ethynylestradiol injections in rats.
2006 Sep
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
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
Patents

Patents

06440987
2
08816084
2
20090062544
2
20090170888
2
20100120815
2
20100130524
2
JP2003526594A
2

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.
Name Type Language
NALFURAFINE HYDROCHLORIDE
JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
2-PROPENAMIDE, N-((5.ALPHA.,6.BETA.)-17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-3,14-DIHYDROXYMORPHINAN-6-YL)-3-(3-FURANYL)-N-METHYL-, MONOHYDROCHLORIDE, (2E)-
Common Name English
(-)-17-(CYCLOPROPYLMETHYL-3,14.BETA.-DIHYDROXY-4,5.ALPHA.-EPOXY-6.BETA.-(N-METHYL-TRANS-3-(3-FURYL)ACRYLAMID)MORPHINAN HYDROCHLORIDE
Common Name English
NALFURAFINE HCL
Common Name English
NALFURAFINE HYDROCHLORIDE [MART.]
Common Name English
NALFURAFINE HYDROCHLORIDE [MI]
Common Name English
NALFURAFINE HYDROCHLORIDE [USAN]
Common Name English
TRK-820
Code English
REMITCH
Brand Name English
NALFURAFINE HYDROCHLORIDE [JAN]
Common Name English
Nalfurafine hydrochloride [WHO-DD]
Common Name English
(E)-N-[17-(Cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan-6β-yl]-3-(furan-3-yl)-N-methylprop-2-enamide monohydrochloride
Systematic Name English
NOPICOR
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
EU-Orphan Drug EU/3/02/115
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
Code System Code Type Description
CAS
152658-17-8
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
JAPANESE REVIEW
NOPICOR
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY APPROVED DECEMBER 2014
USAN
SS-122
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
EVMPD
SUB32294
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
NCI_THESAURUS
C80586
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
SMS_ID
100000124346
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
FDA UNII
25CC4N0P8J
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
MERCK INDEX
m7713
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID70426071
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
PUBCHEM
6918287
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL267495
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY
JAPANESE REVIEW
REMITCH
Created by admin on Fri Dec 15 15:26:48 GMT 2023 , Edited by admin on Fri Dec 15 15:26:48 GMT 2023
PRIMARY APPROVED JANUARY 2009
ACTIVE MOIETY
Structure of NALFURAFINE
NIH
NCATS
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