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Compound Detail

CHEMBL142635

NAFTOPIDIL
💊 Approved Drug
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💊 Approved Drug
COc1ccccc1N1CCN(CC(O)COc2cccc3ccccc23)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL142635
Name NAFTOPIDIL
Phase Approved
Structure Type MOL
InChI Key HRRBJVNMSRJFHQ-UHFFFAOYSA-N

Known Names

Flivas Naftopidil NSC-759293
21
Targets
43
Activities
4
Assay Types
2
PK Parameters
20
Publications
3
Known Names
1
Indications
1
Mechanisms

Molecular Properties

392.5
MW (Da)
3.41
ALogP
5
HBA
1
HBD
45.2
PSA (Ų)
0.67
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Unknown
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -dil

Extended Properties

Molecular Formula C24H28N2O3
MW 392.50
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.03

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Alpha-1d adrenergic receptor antagonist ANTAGONIST Alpha-1D adrenergic receptor ✓ ✓

Indications

Hyperplasia

Activity Summary

IC50 25 meas. best 7.26
Ki 9 meas. best 8.92
Kd 7 meas. best 7.93
EC50 2 meas. best 4.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1D adrenergic receptor
CHEMBL223
 Ki 8.92 8.92 1.2 1
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 8.43 8.33 3.7 4
Alpha-1D adrenergic receptor
CHEMBL326
 Kd 7.93 7.5667 11.8 3
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 7.7 7.7 19.9 1
Alpha-1A adrenergic receptor
CHEMBL319
 Kd 7.48 7.48 33.1 2
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 7.41 7.41 39.0 1
Alpha-1D adrenergic receptor
CHEMBL223
 IC50 7.26 7.26 55.2 2
Alpha-1B adrenergic receptor
CHEMBL315
 Kd 6.75 6.75 177.8 2
Alpha-1A adrenergic receptor
CHEMBL229
 IC50 6.26 6.26 555.0 2
Alpha-1B adrenergic receptor
CHEMBL232
 IC50 6.2 6.2 634.0 2
Beta-2 adrenergic receptor
CHEMBL2289
 Ki 6.0 6.0 1000.0 1
Adrenergic receptor alpha-2
CHEMBL2093864
 Ki 5.8 5.8 1600.0 1
Trypanosoma cruzi
CHEMBL368
 EC50 4.96 4.96 11000.0 1
786-0
CHEMBL613102
 IC50 4.88 4.88 13300.0 1
ADMET
CHEMBL612558
 EC50 4.75 4.75 18000.0 1
T-24
CHEMBL614774
 IC50 4.73 4.73 18500.0 1
KK-47 cell line
CHEMBL614674
 IC50 4.72 4.72 19000.0 1
DU-145
CHEMBL613508
 IC50 4.68 4.542 21100.0 5
LNCaP
CHEMBL612518
 IC50 4.65 4.65 22360.0 3
Unchecked
CHEMBL612545
 IC50 4.64 4.64 23000.0 1
PNT1A
CHEMBL4513131
 IC50 4.57 4.57 27000.0 1
PC-3
CHEMBL390
 IC50 4.51 4.4233 31200.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.48 4.43 33200.0 2
HEK293
CHEMBL614818
 IC50 4.33 4.33 47300.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 201.5 ng.hr.mL-1 Rattus norvegicus
Cmax 280.51 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-1D adrenergic receptor Ki = 1.202 nM 8.92 Displacement of [125I-HEAT from human alpha1D-adrenoreceptor expressed in CHOK1 ... 29422390
Alpha-1A adrenergic receptor Ki = 3.7 nM 8.43 Binding constant measured against Alpha-1A adrenergic receptor in human prostate... 15664832
Alpha-1A adrenergic receptor Ki = 3.715 nM 8.43 Displacement of [125I-HEAT from human alpha1A-adrenoreceptor expressed in CHOK1 ... 29422390
Alpha-1A adrenergic receptor Ki = 5.888 nM 8.23 Binding affinity to adrenergic alpha1A receptor (unknown origin) -
Alpha-1A adrenergic receptor Ki = 5.88 nM 8.23 Binding affinity to adrenergic alpha1A receptor (unknown origin) -
Alpha-1D adrenergic receptor Kd = 11.75 nM 7.93 Antagonist activity at Sprague-Dawley rat thoracic aorta adrenergic alpha-1D rec... 25874333
Alpha-1D adrenergic receptor Kd = 11.75 nM 7.93 Antagonist activity at alpha1D-adrenoreceptor in Sprague-Dawley rat thoracic aor... 29422390
Alpha-1B adrenergic receptor Ki = 19.95 nM 7.7 Displacement of [125I-HEAT from human alpha1B-adrenoreceptor expressed in CHOK1 ... 29422390
Alpha-1A adrenergic receptor Kd = 33.11 nM 7.48 Antagonist activity at Sprague-Dawley rat prostatic vas deferens adrenergic alph... 25874333
Alpha-1A adrenergic receptor Kd = 33.11 nM 7.48 Antagonist activity at alpha1A-adrenoreceptor in Sprague-Dawley rat vas deferens... 29422390
Adrenergic receptor alpha-1 Ki = 39.0 nM 7.41 Alpha-1 adrenergic receptor binding affinity by measuring the displacement of [3... 10743949
Alpha-1D adrenergic receptor IC50 = 55.2 nM 7.26 Antagonist activity at alpha 1D adrenergic receptor (unknown origin) by lucifera... 29615343
Alpha-1D adrenergic receptor IC50 = 55.2 nM 7.26 Antagonist activity at adrenergic alpha1D receptor (unknown origin) by firefly a... 26643219
Alpha-1D adrenergic receptor Kd = 143.22 nM 6.84 Antagonist activity at alpha-1D adrenergic receptor in SPF rat vas thoracic aort... 31078380
Alpha-1B adrenergic receptor Kd = 177.83 nM 6.75 Antagonist activity at Sprague-Dawley rat spleen adrenergic alpha-1B receptor af... 25874333
Alpha-1B adrenergic receptor Kd = 177.83 nM 6.75 Antagonist activity at alpha1B-adrenoreceptor in Sprague-Dawley rat spleen asses... 29422390
Alpha-1A adrenergic receptor IC50 = 555.0 nM 6.26 Antagonist activity at alpha 1A adrenergic receptor (unknown origin) by lucifera... 29615343
Alpha-1A adrenergic receptor IC50 = 555.0 nM 6.26 Antagonist activity at adrenergic alpha1A receptor (unknown origin) by firefly a... 26643219
Alpha-1B adrenergic receptor IC50 = 634.0 nM 6.2 Antagonist activity at alpha 1B adrenergic receptor (unknown origin) by lucifera... 29615343
Alpha-1B adrenergic receptor IC50 = 634.0 nM 6.2 Antagonist activity at adrenergic alpha1B receptor (unknown origin) by firefly a... 26643219

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 84
31158845 10.1038/s41586-019-1291-3 ADMET 69
31078380 10.1016/j.bmc.2019.05.004 Rattus norvegicus 25
35483137 10.1016/j.bmc.2022.116776 Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
29422390 10.1016/j.bmcl.2018.01.068 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
31083995 10.1021/acs.jmedchem.8b01325 Unchecked 3
29615343 10.1016/j.bmcl.2018.03.070 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
29422390 10.1016/j.bmcl.2018.01.068 Thoracic aorta 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
25874333 10.1016/j.ejmech.2015.04.005 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3

Data from ChEMBL 36 via Core Engine