Compound Detail

CHEMBL27

PROPRANOLOL

💊 Approved Drug

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💊 Approved Drug

CC(C)NCC(O)COc1cccc2ccccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL27
Name	PROPRANOLOL
Phase	Approved
Structure Type	MOL
InChI Key	AQHHHDLHHXJYJD-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

.beta.-propranolol AY-64043- Betalong Dl-propranolol Euprovasin Inderide-40/25 Inderide-80/25 Propranolol Proprasylyt Reducor

Targets

148

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

259.4

MW (Da)

2.58

ALogP

HBA

HBD

41.5

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1967
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Stem	-olol
USAN Year	1965

Extended Properties

Molecular Formula	C16H21NO2
MW	259.35
Aromatic Rings	2
Heavy Atoms	19
NP-Likeness	-0.47

Indications

Cardiovascular Diseases Arrhythmias, Cardiac Ascites Brain Injuries Colorectal Neoplasms Coronary Disease Death, Sudden, Cardiac Esophageal and Gastric Varices Headache Heart Diseases Hemangioma Hypertension, Portal Liver Cirrhosis Migraine Disorders Myocardial Infarction Myocardial Ischemia Smoking Cessation Stress Disorders, Post-Traumatic Tachycardia, Supraventricular Telangiectasia, Hereditary Hemorrhagic

ATC Classification

C07AA05

propranolol

Level 1: CARDIOVASCULAR SYSTEM

Level 2: BETA BLOCKING AGENTS

Activity Summary

Kd 64 meas. best 10.0

IC50 44 meas. best 9.32

Ki 37 meas. best 9.49

EC50 3 meas. best 4.5

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Beta-2 adrenergic receptor CHEMBL210	Kd	10.0	8.952	0.1	5
Beta-2 adrenergic receptor CHEMBL210	Ki	9.49	9.028	0.3	5
Beta-2 adrenergic receptor CHEMBL210	IC50	9.32	8.7075	0.5	4
Beta-2 adrenergic receptor CHEMBL5414	Kd	9.01	8.2958	1.0	12
Cavia porcellus CHEMBL369	Kd	8.9	8.4233	1.3	6
Adrenergic receptor beta CHEMBL2094118	Kd	8.9	8.665	1.3	4
Beta-1 adrenergic receptor CHEMBL213	Ki	8.85	8.5625	1.4	4
Unchecked CHEMBL612545	Kd	8.81	8.4467	1.5	3
Beta-1 adrenergic receptor CHEMBL5471	Kd	8.76	8.3086	1.7	14
Beta-2 adrenergic receptor CHEMBL2289	Kd	8.75	8.75	1.8	1
Beta-1 adrenergic receptor CHEMBL213	Kd	8.74	7.8867	1.8	3
Adrenergic receptor beta CHEMBL2095166	Ki	8.62	7.5367	2.4	3
Beta-1 adrenergic receptor CHEMBL3252	Kd	8.62	7.73	2.4	4
Beta-1 adrenergic receptor CHEMBL3440	Ki	8.62	8.62	2.4	1
Beta-1 adrenergic receptor CHEMBL213	IC50	8.6	7.65	2.5	3
Adrenergic receptor beta CHEMBL2095166	IC50	8.52	8.02	3.0	2
Beta-1 adrenergic receptor CHEMBL3252	Ki	8.52	7.5111	3.0	9
Adrenergic receptor beta CHEMBL2094118	IC50	8.4	8.16	4.0	2
Unchecked CHEMBL612545	Ki	8.15	6.91	7.0	2
Canis familiaris CHEMBL373	Kd	7.95	7.66	11.2	3
Beta-2 adrenergic receptor CHEMBL2289	IC50	7.77	7.77	17.0	1
Beta-2 adrenergic receptor CHEMBL5414	IC50	7.54	7.54	28.8	1
Beta-1 adrenergic receptor CHEMBL5471	IC50	7.46	7.46	34.7	1
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	7.3	7.3	50.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.05	6.9533	90.0	3
Beta-3 adrenergic receptor CHEMBL246	Ki	7.0	7.0	99.0	1
Beta-3 adrenergic receptor CHEMBL246	IC50	6.88	6.88	132.0	1
Beta-3 adrenergic receptor CHEMBL246	Kd	6.79	6.73	162.2	2
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.7	6.7	202.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.66	6.66	218.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.61	6.61	243.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.47	6.47	342.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	6.42	6.42	380.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.38	6.38	419.0	1
Nuclear receptor subfamily 2 group E member 1 CHEMBL1961788	Kd	6.3	6.3	500.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.92	5.92	1206.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.92	5.92	1202.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	5.85	5.85	1423.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.83	5.83	1466.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	5.72	5.5733	1900.0	3
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	5.68	5.68	2100.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	5.64	5.64	2294.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.55	5.55	2828.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	5.54	5.54	2870.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	5.51	5.51	3065.0	1
Unchecked CHEMBL612545	IC50	5.46	5.46	3467.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.4	5.4	4000.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	5.4	5.4	3981.1	1
Hepatic sodium/bile acid cotransporter CHEMBL5287	IC50	5.26	5.26	5500.0	1
Plasmodium falciparum CHEMBL364	IC50	4.99	4.705	10190.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	92.0	mL.min-1.kg-1	Rattus norvegicus
CL	34.0	mL.min-1.kg-1	Canis lupus familiaris
CL	13.0	mL.min-1.kg-1	Homo sapiens
CL	80.0	mL.min-1.g-1	Homo sapiens
CL	16.11	mL.min-1.kg-1	Homo sapiens
CL	12.0	mL.min-1.kg-1	Homo sapiens
CL	10.8	mL.min-1.kg-1	Homo sapiens
CL	12.0	mL.min-1.kg-1	Homo sapiens
CL	92.0	mL.min-1.kg-1	Rattus norvegicus
CL	12.0	mL.min-1.kg-1	Homo sapiens
CL	14.0	mL.min-1.kg-1	Macaca
CL	15.0	mL.min-1.kg-1	Homo sapiens
CL	34.0	mL.min-1.kg-1	Canis lupus familiaris
CL	121.0	mL.min-1.g-1	Mus musculus
CL	121.0	mL.min-1.g-1	Mus musculus
CL	13.0	mL.min-1.kg-1	Homo sapiens
CL	18.3	mL.min-1.kg-1	Homo sapiens
CL	914.5	mL.min-1.g-1	Mus musculus
CL	3600.9	mL.min-1.kg-1	Mus musculus
CL	87.8	mL.min-1.kg-1	Mus musculus
CL	2.7e-05	mL.min-1.g-1	Homo sapiens
CL	4e-06	mL.min-1.g-1	Homo sapiens
CL	260.0	mL.min-1.kg-1	Homo sapiens
CL	48.6	uL.min-1.(10^6cells)-1	Homo sapiens
CL	13.2	mL.min-1.kg-1	Homo sapiens
CL	132.0	mL.min-1.kg-1	Homo sapiens
CL	0.7	mL.min-1.kg-1	Homo sapiens
CL	20.0	mL.min-1.kg-1	Homo sapiens
CL	11.31	mL.min-1.g-1	Rattus norvegicus
CL	7.5	mL.min-1.g-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Beta-2 adrenergic receptor	Kd	=	0.1	nM	10.0	Displacement of [3H]DHA from inactive/G protein-uncoupled human beta2-AR express...	27239696
Beta-2 adrenergic receptor	Kd	=	0.2399	nM	9.62	Antagonist activity at human beta-2 adrenergic receptor expressed in salbutamol-...	21870877
Beta-2 adrenergic receptor	Ki	=	0.32	nM	9.49	Displacement of [3H]CGP12177 from human beta2 adrenoceptor expressed in CHO cell...	31151791
Beta-2 adrenergic receptor	Ki	=	0.46	nM	9.34	Displacement of [3H]-CGP-12177 from human beta2 adrenergic receptor expressed in...	24326276
Beta-2 adrenergic receptor	IC50	=	0.48	nM	9.32	Antagonist activity at ADRB2 endogenously expressed in HEK293 cells transfected ...	32686936
Beta-2 adrenergic receptor	IC50	=	0.55	nM	9.26	Antagonist activity at ADRB2 endogenously expressed in HEK293 cells transfected ...	32686936
Beta-2 adrenergic receptor	Kd	=	0.6026	nM	9.22	Displacement of [3H]-CGP 12177 from human beta-2 adrenergic receptor expressed i...	21870877
Beta-2 adrenergic receptor	Ki	=	0.767	nM	9.12	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Beta-2 adrenergic receptor	Kd	=	0.79	nM	9.1	Binding affinity to human adrenergic beta2 receptor	19168263
Beta-2 adrenergic receptor	Kd	=	0.9772	nM	9.01	In vitro inhibitory activity against beta-2 adrenergic receptor was measured by ...	2872332
Beta-2 adrenergic receptor	IC50	=	1.116	nM	8.95	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Adrenergic receptor beta	Kd	=	1.259	nM	8.9	In vitro blocking of beta adrenergic receptor in guinea pig trachea	6146718
Beta-2 adrenergic receptor	Kd	=	1.259	nM	8.9	Ability to block Beta-2 adrenergic receptor in guinea pig trachea preparation	6130154
Cavia porcellus	Kd	=	1.259	nM	8.9	Inhibition of isoproterenol-induced responses in guinea pig trachea.	6135805
Beta-2 adrenergic receptor	Kd	=	1.38	nM	8.86	Antagonist activity at beta2 adrenoceptor in guinea pig trachea assessed as inhi...	31474
Beta-1 adrenergic receptor	Ki	=	1.4	nM	8.85	Displacement of [3H]CGP12177 from human beta1 adrenoceptor expressed in HEK293T ...	31151791
Beta-1 adrenergic receptor	Ki	=	1.468	nM	8.83	DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol)	-
Unchecked	Kd	=	1.549	nM	8.81	Evaluated for Adrenoceptor from guinea pig left atrium by using isoproterenol as...	6124636
Beta-1 adrenergic receptor	Kd	=	1.738	nM	8.76	In vitro beta-1 adrenergic receptor activity was determined via inhibition of th...	6134834
Beta-2 adrenergic receptor	Ki	=	1.738	nM	8.76	Displacement of [3H]-CGP12177 from human beta2 ADR expressed in HEK293T cell mem...	29851481

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1280
-	10.6019/CHEMBL3885881	Rattus norvegicus	492
2891852	10.1021/jm00396a015	Oryctolagus cuniculus	50
23538234	10.1016/j.bmc.2013.02.044	Rattus norvegicus	24
23378628	10.1124/dmd.112.050054	ADMET	22
8765508	10.1021/jm960122v	Oryctolagus cuniculus	18
21245286	10.1124/dmd.110.036806	Liver	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
6687480	10.1021/jm00356a021	Canis familiaris	14
2164340	10.1177/000348949009900717	Unchecked	13
36796127	10.1016/j.bmc.2023.117203	No relevant target	12
22752	10.1021/jm00199a025	Canis familiaris	12
11602674	-	ATP-dependent translocase ABCB1	11
26565745	10.1021/acs.jmedchem.5b01088	No relevant target	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
7908697	10.1021/jm00033a011	Rattus norvegicus	10
24637077	10.1016/j.ejmech.2014.02.048	Rattus norvegicus	10
15920768	10.1002/jps.20373	ADMET	8
28993106	10.1016/j.bmc.2017.09.037	ADMET	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8

Data from ChEMBL 36 via Core Engine