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Compound Detail

CHEMBL776

METAPROTERENOL
💊 Approved Drug
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💊 Approved Drug
CC(C)NCC(O)c1cc(O)cc(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL776
Name METAPROTERENOL
Phase Approved
Structure Type MOL
InChI Key LMOINURANNBYCM-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Orciprenalina Orciprenaline
2
Targets
3
Activities
1
Assay Types
1
PK Parameters
20
Publications
2
Known Names
1
Indications

Molecular Properties

211.3
MW (Da)
1.13
ALogP
4
HBA
4
HBD
72.7
PSA (Ų)
0.60
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1973
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral Topical

Flags

Withdrawn Natural Product
USAN Year 1964

Extended Properties

Molecular Formula C11H17NO3
MW 211.26
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 0.55

Indications

Lung Diseases, Obstructive

ATC Classification

R03AB03
orciprenaline
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R03CB03
orciprenaline
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Drug Warnings

Withdrawn
cardiotoxicity
Low bronchodilating efficacy (compared to salbutamol) and high incidence of cardiac side effects, mainly palpitations and tachycardia due to its nonselectivity.
Country: United Kingdom   Year: 2009
Withdrawn
cardiotoxicity
Low bronchodilating efficacy (compared to salbutamol) and high incidence of cardiac side effects, mainly palpitations and tachycardia due to its nonselectivity.
Country: United Kingdom   Year: 2009

Activity Summary

Kd 3 meas. best 6.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL210
 Kd 6.3 5.81 501.2 2
Beta-2 adrenergic receptor
CHEMBL3373
 Kd 5.04 5.04 9120.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 20.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor Kd = 501.19 nM 6.3 Binding affinity to beta-2 adrenergic receptor (unknown origin) at 1 to 10000 nM 23954364
Beta-2 adrenergic receptor Kd = 4810.0 nM 5.32 Binding affinity to human adrenergic beta2 receptor 19168263
Beta-2 adrenergic receptor Kd = 9120.0 nM 5.04 Affinity for cow beta-2 adrenergic receptor by measuring displacement (-)-[3H]di... 2993621

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
6115058 10.1021/jm00135a015 Canis familiaris 5
2836587 10.1021/jm00401a004 Beta-2 adrenergic receptor 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
2993621 10.1021/jm00147a037 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2
21624500 10.1016/j.drudis.2011.05.007 Hepatotoxicity 1
20022146 10.1016/j.ejmech.2009.11.034 Homo sapiens 1
23954364 10.1016/j.bmcl.2013.07.052 Beta-2 adrenergic receptor 1
23954364 10.1016/j.bmcl.2013.07.052 Unchecked 1
19168263 10.1016/j.ejmech.2008.12.016 Beta-2 adrenergic receptor 1
22961681 10.1124/dmd.112.047068 Bile salt export pump 1
7154001 10.1021/jm00354a004 Unchecked 1

Data from ChEMBL 36 via Core Engine