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Compound Detail

CHEMBL266195

ALPRENOLOL
🧪 Phase II
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🧪 Phase II
C=CCc1ccccc1OCC(O)CNC(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL266195
Name ALPRENOLOL
Phase Phase II
Structure Type MOL
InChI Key PAZJSJFMUHDSTF-UHFFFAOYSA-N

Known Names

Alprenolol NSC-759561
8
Targets
26
Activities
3
Assay Types
26
PK Parameters
20
Publications
2
Known Names
1
Indications

Molecular Properties

249.3
MW (Da)
2.15
ALogP
3
HBA
2
HBD
41.5
PSA (Ų)
0.69
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

Natural Product
USAN Stem -olol
USAN Year 1968

Extended Properties

Molecular Formula C15H23NO2
MW 249.35
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.24

Indications

Cardiovascular Diseases

ATC Classification

C07AA01
alprenolol
Level 1: CARDIOVASCULAR SYSTEM
Level 2: BETA BLOCKING AGENTS

Activity Summary

Kd 10 meas. best 9.53
IC50 9 meas. best 8.94
Ki 7 meas. best 9.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL210
 Kd 9.53 9.122 0.3 5
Beta-2 adrenergic receptor
CHEMBL210
 Ki 9.3 9.035 0.5 4
Beta-2 adrenergic receptor
CHEMBL210
 IC50 8.94 8.56 1.1 3
Adrenergic receptor beta
CHEMBL2094118
 IC50 8.64 8.64 2.3 1
Beta-1 adrenergic receptor
CHEMBL213
 Ki 8.55 8.55 2.8 1
Beta-2 adrenergic receptor
CHEMBL3373
 IC50 8.53 8.53 3.0 1
Beta-1 adrenergic receptor
CHEMBL213
 Kd 8.37 7.69 4.3 3
Beta-1 adrenergic receptor
CHEMBL213
 IC50 8.31 8.085 4.9 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.67 7.67 21.6 1
Beta-3 adrenergic receptor
CHEMBL246
 Kd 7.12 6.99 75.9 2
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 6.93 6.93 117.5 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 IC50 6.2 6.2 630.0 1
Squalene synthase
CHEMBL3815
 IC50 5.38 5.38 4200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 14.4 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 13.18 uL.min-1.(10^6cells)-1 Homo sapiens
CL 150.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 117.0 mL.min-1.kg-1 Homo sapiens
CL 49.3 uL.min-1.(10^6cells)-1 Homo sapiens
CL 25.1 uL.min-1.(10^6cells)-1 Homo sapiens
CL 12.5 mL.min-1.kg-1 Homo sapiens
F 20.0 % Homo sapiens
F 96.0 % Homo sapiens
Fu 0.24 - -
Fu 0.028 - -
Fu 0.24 - Homo sapiens
Fu 0.18 - Homo sapiens
Fu 0.18 - Homo sapiens
Fu 0.44 - Rattus norvegicus
Fu 0.9 - Homo sapiens
Fu 0.057 - Rattus norvegicus
Fu 0.27 - Not specified
Fu 0.933 - Homo sapiens
Ka 8.11 10'5/M/s Homo sapiens
MRT 3.6 hr Homo sapiens
T1/2 2.5 hr Homo sapiens
Vd 50.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor Kd = 0.2951 nM 9.53 Antagonist activity at human beta-2 adrenergic receptor expressed in salbutamol-... 21870877
Beta-2 adrenergic receptor Ki = 0.5 nM 9.3 Displacement of [3H](-)CGP 12177 from human recombinant beta2 adrenoceptor after... 31303996
Beta-2 adrenergic receptor Kd = 0.5012 nM 9.3 Displacement of [3H]-CGP 12177 from human beta-2 adrenergic receptor expressed i... 21870877
Beta-2 adrenergic receptor Kd = 0.79 nM 9.1 Binding affinity to N-terminal FLAG-tagged C-terminal His-10-tagged human beta2 ... 24454993
Beta-2 adrenergic receptor Ki = 1.0 nM 9.0 Displacement of [3H]-CGP12177 from human recombinant beta2 adrenoceptor expresse... 24454993
Beta-2 adrenergic receptor IC50 = 1.148 nM 8.94 Antagonist activity at beta2 adrenergic receptor (unknown origin) expressed in H... 31298548
Beta-2 adrenergic receptor Ki = 1.2 nM 8.92 Displacement of [3H]DHA from beta2 adrenergic receptor (unknown origin) stably e... 31298548
Beta-2 adrenergic receptor Ki = 1.202 nM 8.92 Displacement of [3H]DHA from beta2 adrenergic receptor (unknown origin) stably e... 31298548
Beta-2 adrenergic receptor Kd = 1.45 nM 8.84 Displacement of [3H]DHA from beta2 adrenergic receptor (unknown origin) stably e... 31298548
Beta-2 adrenergic receptor Kd = 1.445 nM 8.84 Displacement of [3H]DHA from beta2 adrenergic receptor (unknown origin) stably e... 31298548
Adrenergic receptor beta IC50 = 2.3 nM 8.64 Compound was evaluated for its Beta adrenergic receptor blocking action 11459642
Beta-1 adrenergic receptor Ki = 2.818 nM 8.55 Displacement of [3H]DHA from beta1 adrenergic receptor (unknown origin) stably e... 31298548
Beta-2 adrenergic receptor IC50 = 2.98 nM 8.53 Compound was tested for inhibition of [3H]dihydroalprenolol radioligand binding ... 6126588
Beta-2 adrenergic receptor IC50 = 3.3 nM 8.48 Antagonist activity at human recombinant beta2 adrenoreceptor expressed in CHOK1... 31303996
Beta-1 adrenergic receptor Kd = 4.266 nM 8.37 Antagonist activity at human beta-1 adrenergic receptor site 1 expressed in cime... 21870877
Beta-1 adrenergic receptor IC50 = 4.88 nM 8.31 Compound was tested for inhibition of [3H]dihydroalprenolol radioligand binding ... 6126588
Beta-2 adrenergic receptor IC50 = 5.495 nM 8.26 Antagonist activity at beta2 adrenergic receptor (unknown origin) stably express... 31298548
Beta-1 adrenergic receptor Kd = 11.22 nM 7.95 Displacement of [3H]-CGP 12177 from human beta-1 adrenergic receptor expressed i... 21870877
Beta-1 adrenergic receptor IC50 = 13.8 nM 7.86 Antagonist activity at beta1 adrenergic receptor (unknown origin) stably express... 31298548
5-hydroxytryptamine receptor 1A Ki = 21.6 nM 7.67 Displacement of [3H]-OH-DPAT from human recombinant 5-HT1A receptor measured aft... 31303996

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 59
31298548 10.1021/acs.jmedchem.9b00595 Beta-2 adrenergic receptor 10
20070106 10.1021/jm901371v Homo sapiens 8
15658873 10.1021/jm049711o ADMET 5
19397318 10.1021/jm9003945 No relevant target 5
12061889 10.1021/jm0200409 ADMET 5
17418579 10.1016/j.bmc.2007.03.040 ADMET 5
20879794 10.1021/jf102525e No relevant target 4
6131128 10.1021/jm00355a002 Adrenergic receptor beta 4
11300874 10.1021/jm001020e ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
- 10.1016/S0960-894X(97)00046-2 ADMET 4
21870877 10.1021/jm2008562 Beta-1 adrenergic receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
21870877 10.1021/jm2008562 Beta-2 adrenergic receptor 3
2836587 10.1021/jm00401a004 Beta-2 adrenergic receptor 3
21149540 10.1124/dmd.110.035998 Brain 3
19764786 10.1021/jm901036q Plasma 3
11384238 10.1021/jm001101a Homo sapiens 3

Data from ChEMBL 36 via Core Engine