Compound Detail

CHEMBL611

TERAZOSIN

💊 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	CHEMBL611
Name	TERAZOSIN
Phase	Approved
Structure Type	MOL
InChI Key	VCKUSRYTPJJLNI-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Terazosabb Terazosin Terazosina Terazosine

Targets

105

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

387.4

MW (Da)

1.06

ALogP

HBA

HBD

103.0

PSA (Å²)

0.83

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1987
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-azosin
USAN Year	1980

Extended Properties

Molecular Formula	C19H25N5O4
MW	387.44
Aromatic Rings	2
Heavy Atoms	28
NP-Likeness	-0.89

Indications

Prostatic Hyperplasia Atherosclerosis Coronary Disease Diabetes Mellitus, Type 2 Hypercholesterolemia Hypertension Carotid Stenosis Parkinson Disease

ATC Classification

G04CA03

terazosin

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: UROLOGICALS

Activity Summary

Ki 62 meas. best 9.16

Kd 28 meas. best 10.0

IC50 11 meas. best 8.3

EC50 4 meas. best 9.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	Kd	10.0	8.73	0.1	3
Alpha-1B adrenergic receptor CHEMBL232	EC50	9.3	9.03	0.5	2
Alpha-1B adrenergic receptor CHEMBL3122	Ki	9.16	9.16	0.7	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	9.09	8.5067	0.8	3
Alpha-1D adrenergic receptor CHEMBL223	Ki	9.07	8.522	0.8	10
Alpha-1D adrenergic receptor CHEMBL326	Ki	9.0	8.31	1.0	3
Alpha-1B adrenergic receptor CHEMBL232	Ki	8.92	8.593	1.2	10
Alpha-1D adrenergic receptor CHEMBL326	Kd	8.83	8.74	1.5	4
Alpha-1B adrenergic receptor CHEMBL315	Ki	8.72	8.6	1.9	2
Alpha-1A adrenergic receptor CHEMBL229	Ki	8.7	8.2373	2.0	15
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	8.65	8.65	2.2	1
Alpha-1A adrenergic receptor CHEMBL4892	Ki	8.6	8.09	2.5	2
Rattus norvegicus CHEMBL376	Kd	8.6	8.32	2.5	2
Alpha-1B adrenergic receptor CHEMBL315	Kd	8.6	8.596	2.5	5
Adrenergic receptor alpha-1 CHEMBL2094251	IC50	8.3	8.3	5.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	8.22	8.22	6.0	1
Alpha-2B adrenergic receptor CHEMBL266	Ki	8.11	8.11	7.7	1
Alpha-1A adrenergic receptor CHEMBL319	Kd	8.04	7.984	9.1	5
Alpha-1D adrenergic receptor CHEMBL223	IC50	7.77	7.77	17.0	1
Alpha-1A adrenergic receptor CHEMBL3637	Kd	7.7	7.7	19.9	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	7.62	7.62	24.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	Kd	7.6	7.5	25.1	2
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.58	7.045	26.0	4
Canis familiaris CHEMBL373	Kd	7.44	7.16	36.3	3
Alpha-1A adrenergic receptor CHEMBL229	Kd	7.44	7.44	36.3	2
Alpha-1A adrenergic receptor CHEMBL229	EC50	7.29	7.29	51.0	2
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.11	6.652	78.0	5
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.37	6.37	428.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.26	5.812	549.5	5
Unchecked CHEMBL612545	Ki	6.07	6.07	846.0	1
Unchecked CHEMBL612545	IC50	5.9	5.9	1269.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	5.22	5.22	6042.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	4.86	4.86	13832.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	4.75	4.75	17782.8	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.62	4.62	23700.0	1
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	4.43	4.43	36800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	1.1	mL.min-1.kg-1	Homo sapiens
CL	1.1	mL.min-1.kg-1	Homo sapiens
CL	1.0	mL.min-1.kg-1	Homo sapiens
CL	1.1	mL.min-1.kg-1	Homo sapiens
F	49.0	%	Rattus norvegicus
F	49.0	%	Rattus norvegicus
F	49.0	%	Rattus norvegicus
F	80.0	%	Homo sapiens
Fu	0.08	-	Homo sapiens
Fu	0.08	-	Homo sapiens
MRT	15.0	hr	Homo sapiens
T1/2	7.5	hr	Rattus norvegicus
T1/2	7.5	hr	Rattus norvegicus
T1/2	7.5	hr	Rattus norvegicus
T1/2	9.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	Kd	=	0.1	nM	10.0	Antagonist activity at alpha-1-adrenoceptor in rat aorta assessed as inhibition ...	17502340
Unchecked	Kd	=	0.1585	nM	9.8	Antagonist activity at alpha-1L-adrenoceptor in human prostate assessed as inhib...	17502340
Alpha-1B adrenergic receptor	EC50	=	0.5	nM	9.3	Antagonist activity at alpha-1B adrenergic receptor (unknown origin) incubated f...	25813897
Alpha-1B adrenergic receptor	Ki	=	0.69	nM	9.16	In vitro binding affinity using [3H]prazosin as radioligand against adrenoceptor...	10780916
Alpha-1A adrenergic receptor	Ki	=	0.82	nM	9.09	In vitro binding affinity using [3H]prazosin as radioligand against adrenoceptor...	10780916
Alpha-1D adrenergic receptor	Ki	=	0.85	nM	9.07	Binding affinity against human adrenergic receptor subtype Alpha-1D adrenergic r...	9379432
Alpha-1D adrenergic receptor	Ki	=	1.01	nM	9.0	In vitro binding affinity using [3H]prazosin as radioligand against adrenoceptor...	10780916
Alpha-1B adrenergic receptor	Ki	=	1.2	nM	8.92	Compound was tested for its binding affinity utilizing cloned receptor binding a...	9548811
Alpha-1B adrenergic receptor	Ki	=	1.2	nM	8.92	Ability to displace beta ([125I]-iodo-4-hydroxyphenyl)-ethylaminomethyl tetralon...	9873563
Alpha-1D adrenergic receptor	Kd	=	1.479	nM	8.83	Antagonist activity at alpha1D-adrenoreceptor in Sprague-Dawley rat thoracic aor...	29422390
Alpha-1D adrenergic receptor	Kd	=	1.479	nM	8.83	Antagonist activity at Sprague-Dawley rat thoracic aorta adrenergic alpha-1D rec...	25874333
Alpha-1B adrenergic receptor	EC50	=	1.73	nM	8.76	Intrinsic activity at human alpha1B adrenergic receptor expressed in CHOK1 cells...	27658792
Alpha-1B adrenergic receptor	Ki	=	1.9	nM	8.72	Compound was evaluated for its ability to displace [125I]HEAT binding from rat A...	9548811
Alpha-1B adrenergic receptor	Ki	=	1.9	nM	8.72	In vitro binding affinity against Alpha-1B adrenergic receptor of human liver mi...	10579842
Alpha-1B adrenergic receptor	Ki	=	1.9	nM	8.72	In vitro binding affinity against Alpha-1B adrenergic receptor of human liver mi...	10579840
Alpha-1B adrenergic receptor	Ki	=	1.95	nM	8.71	Binding affinity determined by displacement of [3H]prazosin from alpha-1B adrene...	9651170
Alpha-1A adrenergic receptor	Ki	=	2.0	nM	8.7	Compound was evaluated for its affinity for Alpha-1a adrenergic receptor in dog ...	9873563
Alpha-1D adrenergic receptor	Ki	=	2.0	nM	8.7	Compound was tested for its binding affinity utilizing cloned receptor binding a...	9548811
Alpha-1A adrenergic receptor	Ki	=	2.0	nM	8.7	Binding affinity against human adrenergic receptor subtype Alpha-1A adrenergic r...	9379432
Alpha-1D adrenergic receptor	Ki	=	2.0	nM	8.7	Ability to displace beta ([125I]-iodo-4-hydroxyphenyl) ethylamino methyl tetralo...	9873563

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	357
-	10.5281/zenodo.13943903	ADMET	88
31158845	10.1038/s41586-019-1291-3	ADMET	67
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
20070106	10.1021/jm901371v	Homo sapiens	8
38354523	10.1016/j.ejmech.2024.116209	786-0	7
9873563	10.1016/s0960-894x(98)00446-6	Alpha-1A adrenergic receptor	7
38354523	10.1016/j.ejmech.2024.116209	OS-RC-2	7
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	6
10579841	10.1021/jm990201h	Rattus norvegicus	5
10579840	10.1021/jm990200p	Rattus norvegicus	5
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	5
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	4
18426954	10.1124/dmd.108.020479	ADMET	4
18625562	10.1016/j.bmc.2008.06.037	Unchecked	4
10956183	10.1021/jm000085e	Rattus norvegicus	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	4

Data from ChEMBL 36 via Core Engine