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Compound Detail

CHEMBL787

MONTELUKAST
💊 Approved Drug
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💊 Approved Drug
CC(C)(O)c1ccccc1CC[C@@H](SCC1(CC(=O)O)CC1)c1cccc(/C=C/c2ccc3ccc(Cl)cc3n2)c1

Basic Information

ChEMBL ID CHEMBL787
Name MONTELUKAST
Phase Approved
Structure Type MOL
InChI Key UCHDWCPVSPXUMX-TZIWLTJVSA-N
Therapeutic ✓ Yes

Known Names

Brondilat Montelukast Singulair
24
Targets
50
Activities
4
Assay Types
20
PK Parameters
20
Publications
3
Known Names
20
Indications

Molecular Properties

586.2
MW (Da)
8.95
ALogP
4
HBA
2
HBD
70.4
PSA (Ų)
0.17
QED
2
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -ast
USAN Year 1995

Extended Properties

Molecular Formula C35H36ClNO3S
MW 586.20
Aromatic Rings 4
Heavy Atoms 41
NP-Likeness -0.21

Indications

Asthma Asthma, Exercise-Induced Lung Diseases, Obstructive Rhinitis, Allergic Rhinitis, Allergic, Seasonal Rhinitis, Allergic, Seasonal Acne Vulgaris Arthritis, Rheumatoid Diabetic Nephropathies Eosinophilic Esophagitis Multiple Myeloma Pain Respiratory Sounds Rhinitis, Allergic, Perennial Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Sleep Apnea, Obstructive Alzheimer Disease Anemia, Sickle Cell Carcinoma, Non-Small-Cell Lung

ATC Classification

R03DC03
montelukast
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R03DC53
montelukast, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Drug Warnings

Black Box Warning
General Warning
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

IC50 29 meas. best 9.37
Ki 17 meas. best 9.3
Kd 3 meas. best 9.3
EC50 1 meas. best 7.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cysteinyl leukotriene receptor
CHEMBL2094254
IC50 9.37 9.28 0.4 2
Cysteinyl leukotriene receptor 1
CHEMBL1798
IC50 9.3 8.9225 0.5 4
Cysteinyl leukotriene receptor 1
CHEMBL5645
Ki 9.3 8.99 0.5 2
Cysteinyl leukotriene receptor 1
CHEMBL5645
IC50 9.3 9.3 0.5 2
Cavia porcellus
CHEMBL369
Kd 9.3 9.3 0.5 2
Cysteinyl leukotriene receptor 1
CHEMBL1798
Ki 8.94 8.94 1.1 1
Cysteinyl leukotriene receptor 1
CHEMBL1798
EC50 7.14 7.14 72.0 1
Cytochrome P450 2C8
CHEMBL3721
IC50 6.89 6.2633 130.0 3
Adenosine receptor A3
CHEMBL256
Ki 6.61 6.61 245.0 1
Adenosine receptor A3
CHEMBL256
IC50 6.36 6.36 434.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.12 6.12 767.0 1
Mitogen-activated protein kinase 14
CHEMBL260
IC50 6.07 6.07 856.0 1
Substance-K receptor
CHEMBL2327
Ki 5.89 5.89 1274.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.85 5.85 1404.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.83 5.83 1470.0 1
Thromboxane-A synthase
CHEMBL1835
IC50 5.82 5.82 1525.0 1
Delta-type opioid receptor
CHEMBL236
Ki 5.77 5.77 1690.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.71 5.71 1938.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.68 5.68 2067.0 1
Beta-2 adrenergic receptor
CHEMBL210
Ki 5.62 5.62 2398.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.58 5.58 2631.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.58 5.58 2601.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.57 5.57 2667.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.57 5.57 2689.0 1
Beta-3 adrenergic receptor
CHEMBL246
Ki 5.5 5.5 3200.0 1
Epidermal growth factor receptor
CHEMBL203
IC50 5.5 5.5 3197.0 1
Beta-2 adrenergic receptor
CHEMBL210
IC50 5.46 5.46 3488.0 1
Substance-K receptor
CHEMBL2327
IC50 5.42 5.42 3822.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.41 5.41 3919.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.4 5.4 3981.0 1
Beta-3 adrenergic receptor
CHEMBL246
IC50 5.37 5.37 4300.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
IC50 5.33 5.33 4702.0 1
Delta-type opioid receptor
CHEMBL236
IC50 5.32 5.32 4795.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.28 5.28 5279.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 5.2 5.2 6256.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 5.18 5.18 6626.0 1
Uracil nucleotide/cysteinyl leukotriene receptor
CHEMBL1075162
Ki 5.18 5.18 6540.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.11 5.11 7747.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.09 5.09 8045.0 1
J774.A1
CHEMBL614040
IC50 5.06 5.06 8700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.27 mL.min-1.kg-1 Homo sapiens
CL 0.68 mL.min-1.kg-1 Homo sapiens
CL 0.68 mL.min-1.kg-1 Homo sapiens
CL 0.7 mL.min-1.kg-1 Homo sapiens
CL 0.68 mL.min-1.kg-1 Homo sapiens
CL 14.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 30.0 mL.min-1.g-1 Homo sapiens
CL 43.65 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 1.3 mL.min-1.kg-1 Macaca fascicularis
CL 0.57 mL.min-1.kg-1 Homo sapiens
F 42.0 % Saimiri
F 73.0 % Homo sapiens
F 63.0 % Rattus norvegicus
Fu 0.002 - Homo sapiens
Fu 0.002 - Homo sapiens
Fu 4e-05 - Macaca fascicularis
Fu 4e-05 - Homo sapiens
MRT 3.8 hr Homo sapiens
T1/2 4.0 hr -
T1/2 5.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cysteinyl leukotriene receptor IC50 = 0.43 nM 9.37 In vitro inhibition of [3H]LTD4 binding to LTD4 receptor of guinea pig lung memb... 9871597
Cavia porcellus Kd = 0.5012 nM 9.3 Antagonistic activity of leukotriene D4-induced contractions of non-tonal guinea... -
Cysteinyl leukotriene receptor 1 Ki = 0.5 nM 9.3 Binding affinity towards Cysteinyl leukotriene D4 receptor (cysLT1) was measured... 9554877
Cysteinyl leukotriene receptor 1 IC50 = 0.5 nM 9.3 Compound were tested for inhibitory activity against Cysteinyl leukotriene D4 re... 8709092
Cysteinyl leukotriene receptor 1 IC50 = 0.5 nM 9.3 Concentration required for inhibition of binding of [3H]LTD4 to guinea pig lung ... -
Cysteinyl leukotriene receptor 1 IC50 = 0.5 nM 9.3 Displacement of [3H]LTD4 from LTD4 receptor in guinea pig lung membrane 27299736
Cavia porcellus Kd = 0.5012 nM 9.3 Compound was tested for LTD4 induced guinea pig trachea contraction 8709092
Cysteinyl leukotriene receptor IC50 = 0.64 nM 9.19 In vitro inhibition of [3H]-LTD4 binding to LTD4 receptor of guinea pig lung mem... 9871597
Cysteinyl leukotriene receptor 1 IC50 = 0.78 nM 9.11 In vitro inhibition of [3H]-LTD4 binding to LTD4 receptor of DMSO differentiated... 9871597
Cysteinyl leukotriene receptor 1 Ki = 1.143 nM 8.94 DRUGMATRIX: Cysteinyl leukotriene receptor 1 radioligand binding (ligand: [3H]LT... -
Cysteinyl leukotriene receptor 1 Ki = 2.1 nM 8.68 In vitro binding affinity towards Cysteinyl leukotriene D4 receptor by using [3H... 10669566
Cysteinyl leukotriene receptor 1 IC50 = 2.287 nM 8.64 DRUGMATRIX: Cysteinyl leukotriene receptor 1 radioligand binding (ligand: [3H]LT... -
Cysteinyl leukotriene receptor 1 IC50 = 2.3 nM 8.64 Antagonist activity at human CysLT1 26200813
Cysteinyl leukotriene receptor 1 EC50 = 72.0 nM 7.14 Antagonist activity at CysLT1 receptor in human dU937 cells assessed as inhibiti... 20621485
Cytochrome P450 2C8 IC50 = 130.0 nM 6.89 Inhibition of CYP2C8 in human liver microsomes using paclitaxel as substrate inc... 35609303
Adenosine receptor A3 Ki = 245.0 nM 6.61 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Adenosine receptor A3 IC50 = 434.0 nM 6.36 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Alpha-2C adrenergic receptor Ki = 767.0 nM 6.12 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Mitogen-activated protein kinase 14 IC50 = 856.0 nM 6.07 DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substra... -
Cytochrome P450 2C8 IC50 = 1000.0 nM 6.0 Inhibition of CYP2C8 in human liver microsomes using paclitaxel as substrate upt... 29243920

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
32985885 10.1021/acs.jmedchem.0c01033 ADMET 7
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL3301361 No relevant target 4
- 10.6019/CHEMBL3301361 ADMET 4
31415176 10.1021/acs.jmedchem.9b00555 Leukotriene C4 synthase 3
19505824 10.1016/j.bmcl.2009.05.094 Cavia porcellus 3
20014752 10.1021/tx900326k Hepatotoxicity 3
20621485 10.1016/j.bmc.2010.06.047 Cysteinyl leukotriene receptor 1 3
9871597 10.1016/s0960-894x(98)00051-1 Cysteinyl leukotriene receptor 2
- 10.1016/0960-894X(95)00023-M Mus musculus 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.1016/0960-894X(95)00023-M ADMET 2
- 10.1016/0960-894X(95)00023-M Unchecked 2
18768239 10.1016/j.ejmech.2008.07.027 Hepatocyte 2
19445515 10.1021/jm900403j Homo sapiens 2
20553011 10.1021/tx1000865 Hepatotoxicity 2

Data from ChEMBL 36 via Core Engine