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Compound Detail

CHEMBL490665

NALFURAFINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CN(C(=O)/C=C/c1ccoc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl

Basic Information

ChEMBL ID CHEMBL490665
Name NALFURAFINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key DJSFYNINGIMKAG-FQJQBBMWSA-N
Parent Compound CHEMBL267495
Active Moiety CHEMBL267495

Known Names

Nalfurafine hcl Nalfurafine hydrochloride Nopicor Remitch TRK-820
11
Targets
34
Activities
4
Assay Types
6
PK Parameters
20
Publications
5
Known Names
2
Indications
1
Mechanisms

Molecular Properties

476.6
MW (Da)
3.09
ALogP
6
HBA
2
HBD
86.4
PSA (Ų)
0.65
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Unknown
Chirality Single Enantiomer
USAN Stem nal-
USAN Year 2006

Extended Properties

Molecular Formula C28H33ClN2O5
MW 513.03
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness 1.28

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Kappa opioid receptor agonist AGONIST Kappa-type opioid receptor

Indications

Liver Diseases Kidney Failure, Chronic

Activity Summary

Ki 22 meas. best 9.75
EC50 6 meas. best 10.3
IC50 3 meas. best 9.38
Kd 3 meas. best 9.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
EC50 10.3 10.3 0.1 1
Kappa-type opioid receptor
CHEMBL4329
Ki 9.75 9.75 0.2 1
Kappa-type opioid receptor
CHEMBL3952
Ki 9.75 9.72 0.2 5
Kappa-type opioid receptor
CHEMBL237
Kd 9.72 9.72 0.2 1
Kappa-type opioid receptor
CHEMBL237
Ki 9.62 9.62 0.2 1
Kappa-type opioid receptor
CHEMBL4329
EC50 9.59 9.59 0.3 1
Kappa-type opioid receptor
CHEMBL4329
IC50 9.38 9.38 0.4 1
Mu-type opioid receptor
CHEMBL4354
Ki 9.37 9.305 0.4 2
Mu-type opioid receptor
CHEMBL2858
Ki 9.37 8.926 0.4 5
Mu-type opioid receptor
CHEMBL2858
EC50 9.28 9.28 0.5 1
Mu-type opioid receptor
CHEMBL233
Kd 9.14 9.14 0.7 1
Mu-type opioid receptor
CHEMBL233
EC50 8.77 8.77 1.7 1
Mu-type opioid receptor
CHEMBL233
Ki 8.22 8.22 6.0 1
Delta-type opioid receptor
CHEMBL3222
Ki 7.29 7.22 51.3 4
Unchecked
CHEMBL612545
Ki 7.01 7.01 96.5 1
Delta-type opioid receptor
CHEMBL236
Kd 6.94 6.94 115.9 1
Delta-type opioid receptor
CHEMBL236
EC50 6.85 6.85 141.4 1
Orexin/Hypocretin receptor type 1
CHEMBL5113
Ki 6.6 6.6 250.0 1
Delta-type opioid receptor
CHEMBL236
Ki 6.16 6.16 693.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.17 5.17 6700.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 14000.0 nM Mus musculus
Ke 41.6 nM Mus musculus
Ke 0.16 nM Mus musculus
Ke 0.07 nM Cavia porcellus
Ke 5.5 nM Cavia porcellus
Ke 48.0 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor EC50 = 0.05 nM 10.3 Agonist activity at human recombinant kappa opioid receptor expressed in CHO cel... 23200250
Kappa-type opioid receptor Ki = 0.178 nM 9.75 Displacement of [3H]U69,593 from KOR in mouse whole brain membranes without cere... 26346669
Kappa-type opioid receptor Ki = 0.178 nM 9.75 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum a... 23200250
Kappa-type opioid receptor Ki = 0.178 nM 9.75 Displacement of [3H]U-69,593 from kappa opioid receptor in guinea pig cerebellum... 23103094
Kappa-type opioid receptor Ki = 0.178 nM 9.75 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum 22460026
Kappa-type opioid receptor Kd = 0.19 nM 9.72 Binding affinity to KOR (unknown origin) assessed as dissociation constant 38814086
Kappa-type opioid receptor Ki = 0.195 nM 9.71 Displacement of [3H]U-69,593 from kappa opioid receptor in guinea pig cerebellum 22742909
Kappa-type opioid receptor Ki = 0.23 nM 9.64 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum h... 21641798
Kappa-type opioid receptor Ki = 0.238 nM 9.62 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce... 28051300
Kappa-type opioid receptor EC50 = 0.26 nM 9.59 Agonist activity at mouse KOR expressed in CHO cells increase in [35S]GTPgammaS ... 38814086
Kappa-type opioid receptor IC50 = 0.42 nM 9.38 Agonist activity at kappa opioid receptor in ddy mouse vas deferens assessed as ... 18829333
Mu-type opioid receptor Ki = 0.431 nM 9.37 Displacement of [3H]DAMGO from MOR in guinea pig cerebellum membranes 26346669
Mu-type opioid receptor Ki = 0.431 nM 9.37 Displacement of [3H]DAMGO from mu opioid receptor in mouse whole brain membranes... 23200250
Mu-type opioid receptor Ki = 0.431 nM 9.37 Displacement of [3H]DAMGO from mu opioid receptor in mouse whole brain without c... 22460026
Mu-type opioid receptor Ki = 0.431 nM 9.37 Displacement of [3H]DAMGO from mu opioid receptor in mouse whole brain membranes... 23103094
Mu-type opioid receptor EC50 = 0.52 nM 9.28 Agonist activity at mouse MOR expressed in CHO cells increase in [35S]GTPgammaS ... 38814086
Mu-type opioid receptor Ki = 0.58 nM 9.24 Displacement of [3H]DAMGO from mu opioid receptor in guinea pig forebrain homoge... 21641798
Mu-type opioid receptor Ki = 0.582 nM 9.23 Displacement of [3H]DAMGO from mu opioid receptor in mouse cerebellum 22742909
Mu-type opioid receptor Kd = 0.72 nM 9.14 Binding affinity to MOR (unknown origin) assessed as dissociation constant 38814086
Mu-type opioid receptor EC50 = 1.7 nM 8.77 Agonist activity at mu opioid receptor (unknown origin) 28688957

Literature References

PubMed DOI Target Context # Activities
18829333 10.1016/j.bmc.2008.09.011 Mus musculus 8
38814086 10.1021/acs.jmedchem.4c00646 Mus musculus 7
38814086 10.1021/acs.jmedchem.4c00646 ADMET 4
18829333 10.1016/j.bmc.2008.09.011 Kappa-type opioid receptor 4
23200250 10.1016/j.bmcl.2012.10.100 Kappa-type opioid receptor 3
38814086 10.1021/acs.jmedchem.4c00646 Mu-type opioid receptor 3
38814086 10.1021/acs.jmedchem.4c00646 Delta-type opioid receptor 3
38814086 10.1021/acs.jmedchem.4c00646 Kappa-type opioid receptor 3
22460026 10.1016/j.bmcl.2012.02.082 Mu-type opioid receptor 2
28051300 10.1021/acs.jmedchem.6b01418 Orexin receptor type 2 2
23103094 10.1016/j.bmcl.2012.09.101 Unchecked 2
22742909 10.1016/j.bmcl.2012.05.122 Unchecked 2
26346669 10.1016/j.bmc.2015.08.036 Unchecked 2
22460026 10.1016/j.bmcl.2012.02.082 Unchecked 2
26346669 10.1016/j.bmc.2015.08.036 Mus musculus 2
21641798 10.1016/j.bmcl.2011.04.147 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
18829333 10.1016/j.bmc.2008.09.011 Unchecked 2
38814086 10.1021/acs.jmedchem.4c00646 Unchecked 2
18829333 10.1016/j.bmc.2008.09.011 Mu-type opioid receptor 2

Data from ChEMBL 36 via Core Engine