Compound Detail

CHEMBL429

LABETALOL

💊 Approved Drug

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💊 Approved Drug

CC(CCc1ccccc1)NCC(O)c1ccc(O)c(C(N)=O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL429
Name	LABETALOL
Phase	Approved
Structure Type	MOL
InChI Key	SGUAFYQXFOLMHL-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

AH-5158A FREE BASE Ibidomide Labetalol Normozide SCH-15719W FREE BASE

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

328.4

MW (Da)

2.14

ALogP

HBA

HBD

95.6

PSA (Å²)

0.60

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1984
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Stem	-alol
USAN Year	1976

Extended Properties

Molecular Formula	C19H24N2O3
MW	328.41
Aromatic Rings	2
Heavy Atoms	24
NP-Likeness	-0.21

Indications

Cardiovascular Diseases Hypertension Pre-Eclampsia Cerebral Hemorrhage Cocaine-Related Disorders Sinusitis Stroke Tobacco Use Disorder Pain Hypotension

ATC Classification

C07AG01

labetalol

Level 1: CARDIOVASCULAR SYSTEM

Level 2: BETA BLOCKING AGENTS

Activity Summary

IC50 14 meas. best 8.0

Ki 12 meas. best 8.23

Kd 4 meas. best 7.5

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Beta-1 adrenergic receptor CHEMBL213	Ki	8.23	8.23	5.8	1
Beta-1 adrenergic receptor CHEMBL213	IC50	8.0	8.0	10.0	1
Beta-2 adrenergic receptor CHEMBL210	Ki	7.96	7.96	11.0	1
Beta-2 adrenergic receptor CHEMBL210	IC50	7.8	7.8	16.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	7.64	7.64	23.0	1
Beta-1 adrenergic receptor CHEMBL5471	Kd	7.5	7.5	31.6	1
Beta-2 adrenergic receptor CHEMBL5414	Kd	7.4	7.4	39.8	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	7.24	7.24	57.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	Kd	6.8	6.8	158.5	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	6.65	6.65	225.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	6.59	6.59	256.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.49	6.49	323.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.41	6.41	393.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	6.28	6.28	521.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	6.23	6.23	583.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.12	6.12	763.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.1	6.1	800.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.89	5.89	1277.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	5.79	5.79	1607.0	1
Unchecked CHEMBL612545	Ki	5.76	5.76	1734.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	5.74	5.74	1815.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.71	5.71	1933.0	1
Unchecked CHEMBL612545	IC50	5.55	5.55	2818.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.52	5.52	3037.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.48	5.48	3326.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.47	5.47	3354.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	23.0	mL.min-1.kg-1	Homo sapiens
CL	23.0	mL.min-1.kg-1	Homo sapiens
CL	450.0	mL.min-1.kg-1	Homo sapiens
CL	21.6	uL.min-1.(10^6cells)-1	Homo sapiens
CL	7.47	uL.min-1.(10^6cells)-1	Homo sapiens
CL	18.1	mL.min-1.kg-1	Homo sapiens
CL	5.72	mL.min-1.g-1	Rattus norvegicus
CL	3.34	mL.min-1.g-1	Rattus norvegicus
F	49.0	%	Homo sapiens
Fu	0.5	-	Homo sapiens
Fu	0.5	-	Homo sapiens
Fu	0.32	-	Not specified
Fu	0.961	-	Homo sapiens
Fu	0.519	-	Rattus norvegicus
Fu	0.075	-	Rattus norvegicus
MRT	3.5	hr	Homo sapiens
T1/2	4.4	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Beta-1 adrenergic receptor	Ki	=	5.837	nM	8.23	DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol)	-
Beta-1 adrenergic receptor	IC50	=	10.0	nM	8.0	DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol)	-
Beta-2 adrenergic receptor	Ki	=	11.0	nM	7.96	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Beta-2 adrenergic receptor	IC50	=	16.0	nM	7.8	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Alpha-1A adrenergic receptor	Ki	=	23.0	nM	7.64	DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin)	-
Beta-1 adrenergic receptor	Kd	=	31.62	nM	7.5	The compound was evaluated for the antagonistic activity against beta-1 adrenerg...	3012084
Beta-2 adrenergic receptor	Kd	=	39.81	nM	7.4	The compound was evaluated for the antagonistic activity against beta-2 adrenerg...	3012084
Alpha-1A adrenergic receptor	IC50	=	57.0	nM	7.24	DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin)	-
Adrenergic receptor alpha-1	Kd	=	158.49	nM	6.8	The compound was evaluated for the antagonistic activity against alpha-1 adrener...	3012084
5-hydroxytryptamine receptor 1A	Ki	=	225.0	nM	6.65	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
Alpha-1D adrenergic receptor	Ki	=	256.0	nM	6.59	DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin)	-
Alpha-1B adrenergic receptor	Ki	=	323.0	nM	6.49	DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin)	-
5-hydroxytryptamine receptor 1A	IC50	=	393.0	nM	6.41	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
Alpha-1D adrenergic receptor	IC50	=	521.0	nM	6.28	DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin)	-
Alpha-1B adrenergic receptor	IC50	=	583.0	nM	6.23	DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin)	-
Sigma non-opioid intracellular receptor 1	Ki	=	763.0	nM	6.12	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Cytochrome P450 2D6	IC50	=	800.0	nM	6.1	DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	-
Sodium-dependent dopamine transporter	Ki	=	1277.0	nM	5.89	DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55)	-
Sodium-dependent dopamine transporter	IC50	=	1607.0	nM	5.79	DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55)	-
Unchecked	Ki	=	1734.0	nM	5.76	DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil)	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1394
-	10.6019/CHEMBL3885881	Rattus norvegicus	301
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	67
16472241	10.2174/1570163043334794	Hepatotoxicity	18
21245286	10.1124/dmd.110.036806	Liver	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
3012084	10.1021/jm00156a019	Rattus norvegicus	12
6128421	10.1021/jm00353a017	Rattus norvegicus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
21051535	10.1124/dmd.110.034629	ADMET	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
6118439	10.1021/jm00144a018	Rattus norvegicus	8
9526560	10.1021/jm9704311	ADMET	4
33619967	10.1021/acs.jmedchem.0c02011	ADMET	4
18426954	10.1124/dmd.108.020479	ADMET	4
27241692	10.1016/j.bmcl.2016.05.054	ADMET	4
34547896	10.1021/acs.jmedchem.1c00823	Transthyretin	4
-	10.1007/s00044-010-9454-7	Dipeptidyl peptidase 3	4
20879794	10.1021/jf102525e	No relevant target	4

Data from ChEMBL 36 via Core Engine