Compound Detail

CHEMBL1558

PRAZOSIN HYDROCHLORIDE

💊 Approved Drug

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💊 Approved Drug

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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1558
Name	PRAZOSIN HYDROCHLORIDE
Phase	Approved
Structure Type	MOL
InChI Key	WFXFYZULCQKPIP-UHFFFAOYSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL2
Active Moiety	CHEMBL2

Known Names

Alphavase 0.5 Alphavase 1 Alphavase 2 Alphavase 5 CP-12,299-1 CP-12299-1 Hypovase Hypovase b.d. Kentovace Minipress Minipress xl NSC-292810 +3 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

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

USAN Stem	-azosin
USAN Year	1968

Extended Properties

Molecular Formula	C19H22ClN5O4
MW	419.87
Aromatic Rings	3
Heavy Atoms	28
NP-Likeness	-1.29

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Adrenergic receptor alpha-1 antagonist	ANTAGONIST	Adrenergic receptor alpha-1	✓	✓

Indications

Diabetes Mellitus Hypertension

Activity Summary

IC50 12 meas. best 9.72

Ki 8 meas. best 8.79

Kd 3 meas. best 10.29

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Rattus norvegicus CHEMBL376	Kd	10.29	8.05	0.1	2
Alpha-1B adrenergic receptor CHEMBL315	IC50	9.72	9.72	0.2	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	9.6	9.6	0.3	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	8.79	8.79	1.6	1
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	8.74	8.74	1.8	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	8.69	8.69	2.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	8.46	8.46	3.5	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.4	6.4	396.5	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.21	6.21	617.9	1
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	6.1	6.1	799.6	1
Mu-type opioid receptor CHEMBL233	Ki	5.75	5.75	1791.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.53	5.53	2966.5	1
Plasmodium falciparum CHEMBL364	IC50	5.3	5.0857	5011.9	7

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Rattus norvegicus	Kd	=	0.05129	nM	10.29	Compound was tested for alpha-adrenoceptor blocking activity by its ability to a...	6131135
Alpha-1B adrenergic receptor	IC50	=	0.19	nM	9.72	Displacement of [3H]prazosin from adrenergic Alpha-1B receptor in Wistar rat liv...	19788200
Alpha-1A adrenergic receptor	IC50	=	0.254	nM	9.6	Displacement of [3H]prazosin from adrenergic alpha1A receptor in Wistar rat subm...	19788200
Alpha-1A adrenergic receptor	Ki	=	1.626	nM	8.79	PDSP Secondary Binding target: ADRA1A - Compounds are tested at 10 uM concentrat...	-
Adrenergic receptor alpha-1	Kd	=	1.82	nM	8.74	Alpha-1-Adrenoceptor blocking activity as antagonism of (-)-norepinephrine induc...	2863379
Alpha-1B adrenergic receptor	Ki	=	2.033	nM	8.69	PDSP Secondary Binding target: ADRA1B - Compounds are tested at 10 uM concentrat...	-
Adrenergic receptor alpha-1	Ki	=	3.5	nM	8.46	Displacement of radioligand from rat alpha1 adrenergic receptor by liquid scinti...	9182127
Alpha-2B adrenergic receptor	Ki	=	396.5	nM	6.4	PDSP Secondary Binding target: ADRA2B - Compounds are tested at 10 uM concentrat...	-
Alpha-2C adrenergic receptor	Ki	=	617.94	nM	6.21	PDSP Secondary Binding target: ADRA2C - Compounds are tested at 10 uM concentrat...	-
5-hydroxytryptamine receptor 5A	Ki	=	799.65	nM	6.1	PDSP Secondary Binding target: HTR5A - Compounds are tested at 10 uM concentrati...	-
Rattus norvegicus	Kd	=	1548.82	nM	5.81	Alpha-2-adrenoceptor blocking activity was determined by antagonism of clonidine...	2863379
Mu-type opioid receptor	Ki	=	1791.02	nM	5.75	PDSP Secondary Binding target: OPRM1 - Compounds are tested at 10 uM concentrati...	-
Sigma non-opioid intracellular receptor 1	Ki	=	2966.54	nM	5.53	PDSP Secondary Binding target: SIGMAR1 - Compounds are tested at 10 uM concentra...	-
Plasmodium falciparum	IC50	=	5011.87	nM	5.3	Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr...	19734910
Plasmodium falciparum	IC50	=	6309.57	nM	5.2	Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	7943.28	nM	5.1	Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	10000.0	nM	5.0	Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	10000.0	nM	5.0	Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	10000.0	nM	5.0	Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	10000.0	nM	5.0	Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g...	19734910

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5724801	HEK-293T	304
-	10.6019/CHEMBL5724801	U2OS	304
-	10.6019/CHEMBL5058577	U2OS	304
-	10.6019/CHEMBL5724801	Fibroblast	304
-	10.6019/CHEMBL5058577	HEK-293T	304
-	10.6019/CHEMBL5058577	Fibroblast	304
6131135	10.1021/jm00357a016	Rattus norvegicus	26
-	10.6019/CHEMBL5058564	U2OS	7
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
-	10.6019/CHEMBL5058564	Fibroblast	5
833813	10.1021/jm00211a031	ADMET	4
3941410	10.1021/jm00151a003	Rattus norvegicus	4
-	10.6019/CHEMBL5058564	HEK-293T	4
833813	10.1021/jm00211a031	Canis familiaris	3
21193252	10.1016/j.ejmech.2010.11.045	Felis catus	2
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	2
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	2
-	10.6019/CHEMBL5209801	Apelin receptor	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.6019/CHEMBL5209801	G-protein coupled receptor 35	2

Data from ChEMBL 36 via Core Engine