Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL707

DOXAZOSIN
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
COc1cc2nc(N3CCN(C(=O)C4COc5ccccc5O4)CC3)nc(N)c2cc1OC

Basic Information

ChEMBL ID CHEMBL707
Name DOXAZOSIN
Phase Approved
Structure Type MOL
InChI Key RUZYUOTYCVRMRZ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

C02CA04 Doxazosin Doxazosina Doxazosine UK-33274
30
Targets
79
Activities
4
Assay Types
6
PK Parameters
20
Publications
5
Known Names
20
Indications

Molecular Properties

451.5
MW (Da)
1.72
ALogP
9
HBA
1
HBD
112.3
PSA (Ų)
0.63
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -azosin
USAN Year 1981

Extended Properties

Molecular Formula C23H25N5O5
MW 451.48
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -0.79

Indications

Hypertension Diabetes Mellitus Heart Failure Hypercholesterolemia Kidney Calculi Myocardial Infarction Myocardial Ischemia Paraganglioma Pheochromocytoma Prostatic Hyperplasia Alcoholism Cardiovascular Diseases Cocaine-Related Disorders Cocaine-Related Disorders Heart Diseases Stress Disorders, Post-Traumatic Tobacco Use Disorder Vascular Diseases Erectile Dysfunction Substance-Related Disorders

ATC Classification

C02CA04
doxazosin
Level 1: CARDIOVASCULAR SYSTEM
Level 2: ANTIHYPERTENSIVES

Activity Summary

Ki 31 meas. best 9.49
IC50 29 meas. best 9.13
Kd 12 meas. best 9.51
EC50 7 meas. best 4.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rattus norvegicus
CHEMBL376
Kd 9.51 9.1 0.3 2
Alpha-1B adrenergic receptor
CHEMBL315
Kd 9.51 9.51 0.3 2
Alpha-1D adrenergic receptor
CHEMBL223
Ki 9.49 8.9617 0.3 6
Alpha-1B adrenergic receptor
CHEMBL315
Ki 9.38 9.38 0.4 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 9.27 8.948 0.5 5
Alpha-1B adrenergic receptor
CHEMBL232
Ki 9.2 9.102 0.6 5
Alpha-1A adrenergic receptor
CHEMBL319
Ki 9.2 9.2 0.6 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 9.13 8.97 0.7 2
Alpha-1B adrenergic receptor
CHEMBL315
IC50 9.12 9.12 0.8 1
Alpha-1D adrenergic receptor
CHEMBL326
Kd 8.97 8.97 1.1 1
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 8.96 8.7367 1.1 3
Alpha-1A adrenergic receptor
CHEMBL319
Kd 8.69 8.69 2.0 2
Alpha-1D adrenergic receptor
CHEMBL223
IC50 8.47 8.47 3.4 1
Adrenergic receptor alpha-1
CHEMBL2094251
Kd 8.2 8.2 6.3 1
Alpha-1A adrenergic receptor
CHEMBL229
Kd 7.59 7.59 25.7 1
Canis familiaris
CHEMBL373
Kd 7.59 7.2767 25.7 3
5-hydroxytryptamine receptor 4
CHEMBL5017
Ki 6.9 6.9 127.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.83 6.83 149.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 6.73 6.73 188.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.63 6.63 234.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.55 6.55 280.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.54 6.54 285.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.43 6.43 368.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.26 6.26 544.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.23 5.945 588.8 2
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.14 6.14 729.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
IC50 6.12 6.12 764.0 1
Unchecked
CHEMBL612545
Ki 6.0 6.0 1003.0 1
Unchecked
CHEMBL612545
IC50 5.96 5.96 1100.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.84 5.84 1428.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 5.74 5.74 1815.1 1
Beta-2 adrenergic receptor
CHEMBL210
Ki 5.72 5.72 1889.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.57 5.57 2688.0 1
Beta-2 adrenergic receptor
CHEMBL210
IC50 5.56 5.56 2748.0 1
Interstitial collagenase
CHEMBL332
IC50 5.24 5.24 5749.0 1
4T1
CHEMBL612589
IC50 5.11 5.11 7730.0 1
LNCaP
CHEMBL612518
IC50 4.98 4.6933 10480.0 3
Trypanosoma cruzi
CHEMBL368
EC50 4.92 4.92 12000.0 1
PC-3
CHEMBL390
IC50 4.92 4.56 12100.0 3
ADMET
CHEMBL612558
IC50 4.72 4.69 19000.0 2
MDA-MB-231
CHEMBL400
IC50 4.62 4.62 23930.0 1
BT-549
CHEMBL614072
IC50 4.61 4.61 24820.0 1
ADMET
CHEMBL612558
EC50 4.57 4.57 27000.0 1
DU-145
CHEMBL613508
IC50 4.51 4.4533 30560.0 3
NHDF
CHEMBL614200
EC50 4.39 4.195 40400.0 2
NHDF
CHEMBL614200
IC50 4.37 4.37 43000.0 1
LNCaP
CHEMBL612518
EC50 4.0 4.0 100000.0 1
PC-3
CHEMBL390
EC50 4.0 4.0 100000.0 1
DU-145
CHEMBL613508
EC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.6 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
F 65.0 % Homo sapiens
Fu 0.017 - Homo sapiens
MRT 14.0 hr Homo sapiens
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rattus norvegicus Kd = 0.309 nM 9.51 Antagonist dissociation constant in rat spleen 10780916
Alpha-1B adrenergic receptor Kd = 0.309 nM 9.51 In vitro antagonistic activity against alpha-1B receptor in rat spleen. 11384242
Alpha-1B adrenergic receptor Kd = 0.309 nM 9.51 Antagonist activity at rat Alpha-1B adrenoceptor assessed as inhibition if pheny... 19719240
Alpha-1D adrenergic receptor Ki = 0.3236 nM 9.49 Displacement of [3H]prazosin from human alpha1D adrenoceptor expressed in CHO ce... 28499171
Alpha-1B adrenergic receptor Ki = 0.416 nM 9.38 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1A adrenergic receptor Ki = 0.537 nM 9.27 Displacement of [3H]prazosin from human alpha1A adrenoceptor expressed in CHO ce... 19719240
Alpha-1A adrenergic receptor Ki = 0.537 nM 9.27 Displacement of [3H]prazosin from cloned human ADRA1A expressed in CHO cells 16302814
Alpha-1B adrenergic receptor Ki = 0.631 nM 9.2 Displacement of [3H]prazosin from human alpha1B adrenoceptor expressed in CHO ce... 28499171
Alpha-1A adrenergic receptor Ki = 0.628 nM 9.2 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1A adrenergic receptor IC50 = 0.74 nM 9.13 Displacement of [3H]-prazosin from rat alpha1A adrenergic receptor after 60 mins... 29128116
Alpha-1B adrenergic receptor Ki = 0.74 nM 9.13 Binding affinity against Alpha-1B adrenergic receptor from human clone 7658428
Alpha-1B adrenergic receptor IC50 = 0.751 nM 9.12 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1A adrenergic receptor Ki = 0.7762 nM 9.11 Displacement of [3H]prazosin from human alpha1A adrenoceptor expressed in CHO ce... 28499171
Alpha-1D adrenergic receptor Ki = 0.8128 nM 9.09 Displacement of [3H]prazosin from human Alpha-1D adrenoceptor expressed in CHO c... 19719240
Alpha-1B adrenergic receptor Ki = 0.8128 nM 9.09 Displacement of [3H]prazosin from human Alpha-1B adrenoceptor expressed in CHO c... 19719240
Alpha-1B adrenergic receptor Ki = 0.8128 nM 9.09 Displacement of [3H]prazosin from cloned human ADRA1B expressed in CHO cells 16302814
Alpha-1D adrenergic receptor Ki = 0.8128 nM 9.09 Displacement of [3H]prazosin from cloned human ADRA1D expressed in CHO cells 16302814
Alpha-1B adrenergic receptor Ki = 1.0 nM 9.0 Binding affinity was tested on human Alpha-1B adrenergic receptor 9135028
Alpha-1D adrenergic receptor Kd = 1.072 nM 8.97 Antagonist activity at rat Alpha-1D adrenoceptor assessed as inhibition if norep... 19719240
Adrenergic receptor alpha-1 Ki = 1.1 nM 8.96 Compound was tested for its binding affinity for alpha-1 adrenergic receptor sit... 2879919

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 501
- 10.5281/zenodo.13943903 ADMET 87
31158845 10.1038/s41586-019-1291-3 ADMET 60
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19719240 10.1021/jm8016046 PC-3 7
2879919 10.1021/jm00384a009 Adrenergic receptor alpha-2 6
2879919 10.1021/jm00384a009 Adrenergic receptor alpha-1 6
2879919 10.1021/jm00384a009 Rattus norvegicus 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
16302814 10.1021/jm0580398 PC-3 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
28499171 10.1016/j.ejmech.2017.05.003 LNCaP 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3

Data from ChEMBL 36 via Core Engine