Compound Detail

CHEMBL2

PRAZOSIN

💊 Approved Drug

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💊 Approved Drug

COc1cc2nc(N3CCN(C(=O)c4ccco4)CC3)nc(N)c2cc1OC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2
Name	PRAZOSIN
Phase	Approved
Structure Type	MOL
InChI Key	IENZQIKPVFGBNW-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

CP-122991 Prazosin Prazosina Prazosine

Targets

286

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

383.4

MW (Da)

1.78

ALogP

HBA

HBD

107.0

PSA (Å²)

0.73

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1976
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-azosin
USAN Year	1968

Extended Properties

Molecular Formula	C19H21N5O4
MW	383.41
Aromatic Rings	3
Heavy Atoms	28
NP-Likeness	-1.29

Indications

Hypertension Alcoholism Kidney Calculi Stress Disorders, Post-Traumatic Amphetamine-Related Disorders Severe Acute Respiratory Syndrome Tobacco Use Disorder Anxiety Substance Withdrawal Syndrome Urinary Bladder, Neurogenic

ATC Classification

C02CA01

prazosin

Level 1: CARDIOVASCULAR SYSTEM

Level 2: ANTIHYPERTENSIVES

Activity Summary

Ki 174 meas. best 10.57

IC50 63 meas. best 9.79

Kd 47 meas. best 10.99

EC50 2 meas. best 4.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	10.99	8.8259	0.0	17
Alpha-1B adrenergic receptor CHEMBL232	Ki	10.57	9.3989	0.0	18
Alpha-1A adrenergic receptor CHEMBL229	Ki	10.4	9.4271	0.0	21
Adrenergic receptor alpha-1 CHEMBL2094251	Ki	10.27	10.235	0.1	2
Unchecked CHEMBL612545	Ki	10.15	9.1367	0.1	6
Alpha-1A adrenergic receptor CHEMBL319	Ki	10.15	9.5614	0.1	7
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	10.01	9.5789	0.1	28
Alpha-1B adrenergic receptor CHEMBL315	Ki	10.0	9.59	0.1	7
Alpha-1A adrenergic receptor CHEMBL4892	Ki	9.9	9.46	0.1	4
Alpha-1A adrenergic receptor CHEMBL319	Kd	9.81	8.9975	0.2	4
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	9.79	9.323	0.2	10
Alpha-1D adrenergic receptor CHEMBL223	Ki	9.77	9.5494	0.2	17
Alpha-1D adrenergic receptor CHEMBL326	Kd	9.77	9.06	0.2	5
Adrenergic receptor alpha-1 CHEMBL2094251	IC50	9.77	9.408	0.2	5
Alpha-1B adrenergic receptor CHEMBL315	IC50	9.75	9.4633	0.2	3
Alpha-1D adrenergic receptor CHEMBL326	Ki	9.7	9.295	0.2	4
Alpha-1A adrenergic receptor CHEMBL319	IC50	9.66	9.41	0.2	2
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	9.48	9.48	0.3	1
Beta-casein CHEMBL2210	Ki	9.44	9.44	0.4	1
Adrenergic receptor alpha-1 CHEMBL2094251	Kd	9.42	8.916	0.4	5
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	9.4	6.2513	0.4	23
Alpha-1D adrenergic receptor CHEMBL223	IC50	9.18	9.12	0.7	2
Unchecked CHEMBL612545	IC50	9.17	6.81	0.7	7
Alpha-1B adrenergic receptor CHEMBL3122	Ki	9.08	9.08	0.8	1
Alpha-1B adrenergic receptor CHEMBL315	Kd	9.01	8.9967	1.0	3
Adrenergic receptor alpha-2 CHEMBL2093864	Kd	8.96	6.1722	1.1	9
Alpha-1A adrenergic receptor CHEMBL229	IC50	8.4	8.4	4.0	1
Alpha-1A adrenergic receptor CHEMBL3637	Kd	8.3	8.3	5.0	1
Unchecked CHEMBL612545	Kd	8.26	8.26	5.5	1
Ribosyldihydronicotinamide dehydrogenase [quinone] CHEMBL3959	IC50	8.11	8.11	7.8	1
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	8.1	6.5625	8.0	4
Alpha-1B adrenergic receptor CHEMBL232	IC50	8.06	8.06	8.7	1
Adrenergic receptor alpha CHEMBL2095203	Kd	8.0	8.0	10.0	1
Rattus norvegicus CHEMBL376	Kd	8.0	8.0	10.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.89	7.07	13.0	3
Alpha-2 adrenergic receptor CHEMBL2111338	Ki	7.89	6.8567	13.0	3
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.62	7.2233	24.0	3
Adrenergic receptor alpha-2 CHEMBL2095158	Ki	7.47	6.44	34.0	11
Alpha-2A adrenergic receptor CHEMBL4744	Ki	6.97	6.97	106.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.68	6.1167	210.0	3
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.54	6.54	290.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	6.19	6.19	647.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	5.82	5.82	1500.0	1
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	5.8	5.8	1600.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.8	5.4067	1584.9	3
Alpha-2A adrenergic receptor CHEMBL327	Ki	5.78	5.78	1668.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	5.74	5.37	1840.0	2
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	5.63	5.63	2344.2	2
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.58	5.58	2621.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	5.58	5.58	2638.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	2.7	mL.min-1.kg-1	Homo sapiens
CL	4.7	mL.min-1.kg-1	Homo sapiens
CL	4.5	mL.min-1.kg-1	Homo sapiens
CL	4.7	mL.min-1.kg-1	Homo sapiens
CL	4.7	mL.min-1.kg-1	Homo sapiens
CL	5.37	uL.min-1.(10^6cells)-1	Homo sapiens
CL	12.02	uL.min-1.(10^6cells)-1	Rattus norvegicus
F	79.0	%	Homo sapiens
F	68.0	%	Homo sapiens
Fu	0.06	-	Homo sapiens
Fu	0.06	-	Homo sapiens
Fu	0.1	-	Homo sapiens
Fu	0.053	-	Homo sapiens
Fu	0.37	-	Canis lupus familiaris
Fu	0.35	-	Rattus norvegicus
Fu	0.0797	-	Rattus norvegicus
Fu	0.294	-	Rattus norvegicus
Fu	0.195	-	Rattus norvegicus
Fu	0.104	-	Rattus norvegicus
Fu	0.034	-	Rattus norvegicus
Fu	0.052	-	Rattus norvegicus
Fu	0.264	-	Rattus norvegicus
Fu	0.163	-	Rattus norvegicus
Ke	1.1	nM	Homo sapiens
Ke	1.1	nM	Homo sapiens
MRT	2.6	hr	Homo sapiens
T1/2	2.8	hr	Homo sapiens
T1/2	2.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Adrenergic receptor alpha-1	Kd	=	0.01023	nM	10.99	Alpha-1-adrenolytic activity was assessed in vitro from the ability to inhibit c...	2542561
Alpha-1B adrenergic receptor	Ki	=	0.027	nM	10.57	Binding affinity to recombinant human alpha-1B-Adr expressed in HEK cells assess...	38156970
Alpha-1A adrenergic receptor	Ki	=	0.04	nM	10.4	Displacement of [3H]prazosin from human recombinant alpha1A adrenoceptor express...	24805037
Alpha-1A adrenergic receptor	Ki	=	0.04	nM	10.4	Displacement of [3H]prazosin from human adrenergic alpha1A receptor expressed in...	25557493
Adrenergic receptor alpha-1	Kd	=	0.04169	nM	10.38	Antagonism against Alpha-1 adrenergic receptor of rat aorta	-
Adrenergic receptor alpha-1	Ki	=	0.054	nM	10.27	Binding affinity to adrenergic alpha1 receptor (unknown origin) by radioligand d...	23466604
Adrenergic receptor alpha-1	Ki	=	0.063	nM	10.2	Binding affinity to Alpha 1 receptor (unknown origin) assessed as inhibition con...	28849908
Alpha-1A adrenergic receptor	Ki	=	0.07	nM	10.15	Inhibition of [3H]- prazosin binding against Alpha-1A adrenergic receptor from r...	10602703
Unchecked	Ki	=	0.071	nM	10.15	Displacement of [3H]prazosin from adrenergic alpha1 receptor	21726069
Alpha-1A adrenergic receptor	Ki	=	0.088	nM	10.06	DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin)	-
Adrenergic receptor alpha-1	Ki	=	0.097	nM	10.01	Binding affinity against alpha-1 adrenergic receptor on rat cortex using [3H]-pr...	9667967
Alpha-1B adrenergic receptor	Ki	=	0.099	nM	10.0	DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin)	-
Alpha-1B adrenergic receptor	Ki	=	0.1	nM	10.0	Displacement of [3H]prazosin from adrenergic alpha-1B receptor in rat liver memb...	16723224
Alpha-1A adrenergic receptor	Ki	=	0.1259	nM	9.9	In vitro for the displacement of [3H]prazosin binding to bovine Alpha-1A adrener...	9276013
Alpha-1A adrenergic receptor	Ki	=	0.13	nM	9.89	Binding affinity to recombinant human alpha-1A-Adr expressed in HEK cells assess...	38156970
Adrenergic receptor alpha-1	Ki	=	0.15	nM	9.82	Binding affinity for alpha-1 adrenergic receptor by displacement of [3H]-prazosi...	2894465
Alpha-1A adrenergic receptor	Ki	=	0.15	nM	9.82	Displacement of [3H]prazosin from alpha1-adrenoceptor (unknown origin) in cerebr...	29291438
Alpha-1B adrenergic receptor	Ki	=	0.15	nM	9.82	Inhibition of [3H]- prazosin binding against Alpha-1B adrenergic receptor from r...	10602703
Alpha-1B adrenergic receptor	Ki	=	0.15	nM	9.82	Displacement of [3H]Prazosin from alpha1B adrenergic receptor in Wistar rat live...	23403082
Alpha-1A adrenergic receptor	Kd	=	0.1549	nM	9.81	Partial affinity towards Alpha-1 adrenergic receptor was assessed on rat aortic ...	8523408

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	526
-	10.5281/zenodo.13943903	ADMET	87
31158845	10.1038/s41586-019-1291-3	ADMET	65
2989524	10.1021/jm00145a015	Canis familiaris	38
21051535	10.1124/dmd.110.034629	ADMET	21
7658428	10.1021/jm00018a001	Adrenergic receptor alpha-2	20
31732255	10.1016/j.ejmech.2019.111813	ADMET	19
16472241	10.2174/1570163043334794	Hepatotoxicity	18
20850911	10.1016/j.ejmech.2010.08.064	Rattus norvegicus	16
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
6620302	10.1021/jm00364a014	Rattus norvegicus	11
3361578	10.1021/jm00400a003	Rattus norvegicus	9
6312043	10.1021/jm00364a013	Rattus norvegicus	8
3806618	10.1021/jm00385a022	Rattus norvegicus	8
20070106	10.1021/jm901371v	Homo sapiens	8
6133954	10.1021/jm00360a013	Rattus norvegicus	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
2903929	10.1021/jm00120a003	Rattus norvegicus	7
38968440	10.1021/acs.jmedchem.4c00626	Rattus norvegicus	7

Data from ChEMBL 36 via Core Engine