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Compound Detail

CHEMBL267495

NALFURAFINE
💊 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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267495
Name NALFURAFINE
Phase Approved
Structure Type MOL
InChI Key XGZZHZMWIXFATA-UEZBDDGYSA-N

Known Names

MT-9938 Nalfurafina Nalfurafine
15
Targets
34
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names

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

Routes of Administration

Oral

Flags

Natural Product
USAN Stem nal-
USAN Year 2006

Extended Properties

Molecular Formula C28H32N2O5
MW 476.57
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness 1.28

ATC Classification

V03AX02
nalfurafine
Level 1: VARIOUS
Level 2: ALL OTHER THERAPEUTIC PRODUCTS

Activity Summary

Ki 18 meas. best 10.72
EC50 12 meas. best 10.6
IC50 4 meas. best 10.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 10.72 9.1925 0.0 4
Kappa-type opioid receptor
CHEMBL237
 EC50 10.6 9.436 0.0 5
Kappa-type opioid receptor
CHEMBL4329
 IC50 10.44 10.44 0.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.77 9.7025 0.2 4
Delta-type opioid receptor
CHEMBL269
 Ki 9.43 9.43 0.4 1
Mu-type opioid receptor
CHEMBL4354
 Ki 9.41 9.29 0.4 3
Mu-type opioid receptor
CHEMBL2858
 Ki 9.37 9.37 0.4 1
Kappa-type opioid receptor
CHEMBL3614
 EC50 9.3 8.79 0.5 2
Mitogen-activated protein kinase 3
CHEMBL3385
 EC50 9.26 9.26 0.6 1
Mitogen-activated protein kinase 1
CHEMBL4040
 EC50 9.26 9.26 0.6 1
Mu-type opioid receptor
CHEMBL233
 Ki 9.15 9.15 0.7 1
Mu-type opioid receptor
CHEMBL233
 EC50 9.14 9.14 0.7 1
MAP kinase p38
CHEMBL2094115
 EC50 8.28 8.28 5.2 1
Delta-type opioid receptor
CHEMBL236
 Ki 7.44 7.44 36.5 1
Delta-type opioid receptor
CHEMBL3222
 Ki 7.29 7.29 51.3 1
Delta-type opioid receptor
CHEMBL236
 EC50 7.13 7.13 74.1 1
Orexin/Hypocretin receptor type 1
CHEMBL5113
 IC50 7.08 6.43 82.8 2
Unchecked
CHEMBL612545
 Ki 7.01 7.01 96.5 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.019 nM 10.72 Displacement of [3H]DPDPE from human KOR expressed in HEK293 cell membrane 35007722
Kappa-type opioid receptor EC50 = 0.025 nM 10.6 Agonist activity at human kappa opioid receptor expressed in CHO cells assessed ... 17981041
Kappa-type opioid receptor EC50 = 0.034 nM 10.47 Agonist activity at kappa opioid receptor in human HEK293 cells after 30 mins by... 26411794
Kappa-type opioid receptor IC50 = 0.036 nM 10.44 Agonist activity at KOR receptor in mouse vas deferens assessed as inhibition of... 36179400
Kappa-type opioid receptor EC50 = 0.05 nM 10.3 Agonist activity at human kappa opioid receptor expressed in CHO cells by [35S]G... 25283554
Kappa-type opioid receptor Ki = 0.17 nM 9.77 Displacement of [3H]-U-69593 from kappa opioid receptor in guinea pig brain memb... 26411794
Kappa-type opioid receptor Ki = 0.18 nM 9.74 Displacement of [3H]U-69593 from kappa opioid receptor in guinea pig cerebellum 25283554
Kappa-type opioid receptor Ki = 0.225 nM 9.65 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum 20685120
Kappa-type opioid receptor Ki = 0.225 nM 9.65 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum 21256034
Kappa-type opioid receptor Ki = 0.23 nM 9.64 Binding affinity to kappa opioid receptor 22445285
Kappa-type opioid receptor Ki = 0.23 nM 9.64 Binding affinity to kappa opioid receptor (unknown origin) 23623711
Delta-type opioid receptor Ki = 0.37 nM 9.43 Displacement of [3H]-DPDPE from delta opioid receptor in rat brain membrane afte... 26411794
Mu-type opioid receptor Ki = 0.39 nM 9.41 Displacement of [3H]-DAMGO from mu opioid receptor in guinea pig brain membrane ... 26411794
Mu-type opioid receptor Ki = 0.43 nM 9.37 Displacement of [3H]DAMGO from mu opioid receptor in mouse brain membranes witho... 25283554
Kappa-type opioid receptor EC50 = 0.5 nM 9.3 Agonist activity at GFP-tagged rat kappa opioid receptor expressed in HEK293 cel... 29939744
Mitogen-activated protein kinase 3 EC50 = 0.55 nM 9.26 Inhibition of ERK1 phosphorylation (unknown origin) 31550662
Mitogen-activated protein kinase 1 EC50 = 0.55 nM 9.26 Inhibition of ERK2 phosphorylation (unknown origin) 31550662
Mu-type opioid receptor Ki = 0.582 nM 9.23 Displacement of [3H]DAMGO from mu opioid receptor in guinea pig forebrain 21256034
Mu-type opioid receptor Ki = 0.582 nM 9.23 Displacement of [3H]DAMGO from mu opioid receptor in guinea pig forebrain 20685120
Mu-type opioid receptor Ki = 0.7 nM 9.15 Displacement of [3H]DAMGO from human MOR expressed in HEK293 cell membrane 35007722

Literature References

PubMed DOI Target Context # Activities
29939744 10.1021/acs.jmedchem.8b00435 Kappa-type opioid receptor 8
- 10.6019/CHEMBL5058564 U2OS 7
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
26411794 10.1016/j.bmcl.2015.09.040 Kappa-type opioid receptor 4
- 10.6019/CHEMBL5058564 HEK-293T 4
25283554 10.1016/j.bmcl.2014.09.029 Kappa-type opioid receptor 3
21256034 10.1016/j.bmc.2010.12.035 Unchecked 3
25283554 10.1016/j.bmcl.2014.09.029 Mu-type opioid receptor 3
25283554 10.1016/j.bmcl.2014.09.029 Delta-type opioid receptor 3
- 10.6019/CHEMBL5209801 Apelin receptor 2
32738987 10.1016/j.bmcl.2020.127360 Mus musculus 2
35007722 10.1016/j.bmcl.2022.128527 Unchecked 2
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 2
32738987 10.1016/j.bmcl.2020.127360 ADMET 2
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
20685120 10.1016/j.bmcl.2010.07.035 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2

Data from ChEMBL 36 via Core Engine