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Compound Detail

CHEMBL1263

SALMETEROL
💊 Approved Drug
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💊 Approved Drug
OCc1cc(C(O)CNCCCCCCOCCCCc2ccccc2)ccc1O

Basic Information

ChEMBL ID CHEMBL1263
Name SALMETEROL
Phase Approved
Structure Type MOL
InChI Key GIIZNNXWQWCKIB-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

GR 33343 X GR-33343-X Salmaterol Salmeterol SN408D
30
Targets
109
Activities
4
Assay Types
9
PK Parameters
20
Publications
5
Known Names
8
Indications

Molecular Properties

415.6
MW (Da)
4.11
ALogP
5
HBA
4
HBD
82.0
PSA (Ų)
0.31
QED
0
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Prescription
Chirality Racemic

Routes of Administration

Topical

Flags

Black Box Warning Natural Product
USAN Stem sal-; -terol
USAN Year 1985

Extended Properties

Molecular Formula C25H37NO4
MW 415.57
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness 0.20

Indications

Lung Diseases, Obstructive Asthma Bronchiolitis Obliterans Bronchitis, Chronic Emphysema Pulmonary Disease, Chronic Obstructive Lung Diseases Spinal Cord Injuries

ATC Classification

R03AC12
salmeterol
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

EC50 59 meas. best 10.35
Ki 35 meas. best 9.74
IC50 13 meas. best 8.46
Kd 2 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL210
EC50 10.35 9.6237 0.0 27
Beta-2 adrenergic receptor
CHEMBL210
Ki 9.74 8.6975 0.2 12
Beta-2 adrenergic receptor
CHEMBL210
Kd 9.52 7.74 0.3 2
Beta-2 adrenergic receptor
CHEMBL5414
EC50 8.57 8.1675 2.7 4
Beta-2 adrenergic receptor
CHEMBL5414
IC50 8.46 8.46 3.5 2
Unchecked
CHEMBL612545
EC50 8.3 8.23 5.0 2
Beta-1 adrenergic receptor
CHEMBL5471
EC50 8.3 8.3 5.0 1
Beta-2 adrenergic receptor
CHEMBL210
IC50 8.3 8.065 5.0 2
Oryctolagus cuniculus
CHEMBL374
IC50 7.82 7.82 15.0 1
Beta-1 adrenergic receptor
CHEMBL213
EC50 7.53 6.3713 29.5 16
Sigma intracellular receptor 2
CHEMBL4105907
Ki 7.49 7.49 32.4 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.83 6.83 149.4 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.59 6.59 256.9 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.53 6.53 294.2 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.42 6.42 381.9 1
Beta-1 adrenergic receptor
CHEMBL213
IC50 6.3 6.3 501.2 2
Beta-1 adrenergic receptor
CHEMBL3440
Ki 6.26 6.26 550.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 6.26 6.26 548.7 1
dengue virus type 2
CHEMBL613966
IC50 6.17 6.17 670.0 1
Beta-1 adrenergic receptor
CHEMBL213
Ki 6.16 5.922 694.5 5
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.02 6.02 963.2 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.01 6.01 971.3 1
Beta-3 adrenergic receptor
CHEMBL246
EC50 6.0 5.9286 1000.0 7
5-hydroxytryptamine receptor 1D
CHEMBL1983
Ki 5.99 5.99 1036.3 1
D(3) dopamine receptor
CHEMBL234
Ki 5.98 5.94 1049.0 2
D(4) dopamine receptor
CHEMBL219
Ki 5.97 5.97 1076.3 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.89 5.89 1274.8 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.71 5.71 1942.9 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 5.7 5.7 1985.4 1
Psychosine receptor
CHEMBL3714081
IC50 5.61 5.61 2463.2 1
CX3C chemokine receptor 1
CHEMBL4843
IC50 5.5 5.5 3138.6 1
Adhesion G-protein coupled receptor F1
CHEMBL4523872
IC50 5.47 5.47 3409.7 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.39 5.39 4092.6 1
G-protein coupled receptor 183
CHEMBL3259470
IC50 5.37 5.37 4255.5 1
N-formyl peptide receptor 3
CHEMBL5646
IC50 5.25 5.25 5657.9 1
D(2) dopamine receptor
CHEMBL217
Ki 4.5 4.5 32000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 58.0 mL.min-1.g-1 Homo sapiens
CL 85.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 10.0 % Rattus norvegicus
F 10.0 % Rattus norvegicus
F 66.0 % Canis lupus familiaris
F 10.0 % Rattus norvegicus
F 66.0 % Canis lupus familiaris
T1/2 2.9 hr Rattus norvegicus
T1/2 2.9 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor EC50 = 0.04467 nM 10.35 Agonist activity at human beta2 adrenoreceptor overexpressed in human HEK293 cel... 31753798
Beta-2 adrenergic receptor EC50 = 0.07 nM 10.15 Agonist activity at human recombinant beta-2 adrenoceptor expressed in CHO cells... 17498952
Beta-2 adrenergic receptor EC50 = 0.07 nM 10.15 Agonist activity at human recombinant adrenergic beta-2 receptor expressed in CH... 17897826
Beta-2 adrenergic receptor EC50 = 0.07 nM 10.15 Agonist activity at human recombinant beta2 adrenergic receptor expressed in CHO... 20804199
Beta-2 adrenergic receptor EC50 = 0.07244 nM 10.14 Agonist activity at human beta2 adrenoceptor expressed in HEK293 cells assessed ... 38347756
Beta-2 adrenergic receptor EC50 = 0.07762 nM 10.11 Agonist activity at human beta2 adrenergic receptor expressed in HEK293 cells as... 30392952
Beta-2 adrenergic receptor EC50 = 0.07943 nM 10.1 Agonist activity at beta2-adrenergic receptor (unknown origin) expressed in HEK2... 31042379
Beta-2 adrenergic receptor EC50 = 0.1259 nM 9.9 Agonist activity at beta2-adrenergic receptor (unknown origin) expressed in HEK2... 31042379
Beta-2 adrenergic receptor EC50 = 0.1349 nM 9.87 Agonist activity at human beta2 adrenoreceptor overexpressed in HEK293 cells ass... 34273662
Beta-2 adrenergic receptor Ki = 0.18 nM 9.74 Displacement of [3H]CGP12177 from human beta2 receptor expressed in CHO cells 27132867
Beta-2 adrenergic receptor EC50 = 0.2512 nM 9.6 Agonist activity at human cloned beta2 adrenergic receptor expressed in CHO cell... 19317397
Beta-2 adrenergic receptor EC50 = 0.2512 nM 9.6 Agonist activity at human recombinant beta2 adrenergic receptor expressed in CHO... 20462258
Beta-2 adrenergic receptor EC50 = 0.2512 nM 9.6 Agonist activity at human adrenergic beta2 receptor expressed in CHO cells asses... 21696967
Beta-2 adrenergic receptor EC50 = 0.2512 nM 9.6 Agonist activity at human beta2 receptor expressed in CHO cells assessed as cAMP... 21925889
Beta-2 adrenergic receptor EC50 = 0.2512 nM 9.6 Agonist activity at human beta2 adrenoceptor transfected in CHO cells assessed a... 24359185
Beta-2 adrenergic receptor Ki = 0.25 nM 9.6 Displacement of [3H]-CGP-12177 from human beta2-adrenergic receptor expressed in... 31042379
Beta-2 adrenergic receptor Kd = 0.3 nM 9.52 Displacement of [3H]DHA from inactive/G protein-uncoupled human beta2-AR express... 27239696
Beta-2 adrenergic receptor EC50 = 0.3162 nM 9.5 Agonist activity at human recombinant beta2 receptor assessed as cAMP accumulati... 24813741
Beta-2 adrenergic receptor EC50 = 0.3162 nM 9.5 Agonist activity at human beta2 adrenergic receptor expressed in cells by cAMP a... 24835980
Beta-2 adrenergic receptor EC50 = 0.3162 nM 9.5 Agonist activity at recombinant human beta2-adrenoceptor expressed in whole cell... 22178551

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
38347756 10.1021/acs.jmedchem.3c02074 Rattus norvegicus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
28703592 10.1021/acs.jmedchem.7b00205 Lipid bilayer 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
- 10.6019/CHEMBL5058564 HEK-293T 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
31042379 10.1021/acs.jmedchem.9b00349 Beta-2 adrenergic receptor 8
31042379 10.1021/acs.jmedchem.9b00349 Beta-1 adrenergic receptor 7
21696967 10.1016/j.bmc.2011.05.064 Beta-2 adrenergic receptor 6
19317397 10.1021/jm801016j Beta-1 adrenergic receptor 6
20402514 10.1021/jm100068m Beta-2 adrenergic receptor 6
- 10.6019/CHEMBL3301361 ADMET 6
24813741 10.1016/j.bmcl.2014.04.069 Beta-2 adrenergic receptor 5
31753798 10.1016/j.bmc.2019.115178 Unchecked 5
21925889 10.1016/j.bmc.2011.08.043 Beta-2 adrenergic receptor 5
24359185 10.1021/jm401532g Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5058564 U2OS 5
20804199 10.1021/jm1005989 Canis familiaris 4
19317397 10.1021/jm801016j Unchecked 4

Data from ChEMBL 36 via Core Engine