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Compound Detail

CHEMBL1200681

MONTELUKAST SODIUM
💊 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.[Na+]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200681
Name MONTELUKAST SODIUM
Phase Approved
Structure Type MOL
InChI Key LBFBRXGCXUHRJY-HKHDRNBDSA-M
Therapeutic ✓ Yes
Parent Compound CHEMBL787
Active Moiety CHEMBL787

Known Names

MK-476 Montelukast (as sodium) Montelukast monosodium salt Montelukast sodium NSC-759107 Singulair
10
Targets
12
Activities
3
Assay Types
10
PK Parameters
20
Publications
6
Known Names
13
Indications
1
Mechanisms

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 C35H35ClNNaO3S
MW 608.18
Aromatic Rings 4
Heavy Atoms 41
NP-Likeness -0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cysteinyl leukotriene receptor 1 antagonist ANTAGONIST Cysteinyl leukotriene receptor 1 ✓ ✓

Indications

Asthma Asthma, Exercise-Induced Rhinitis, Allergic Rhinitis, Allergic, Perennial Rhinitis, Allergic, Seasonal Rhinitis, Allergic, Seasonal Bronchiolitis Pulmonary Disease, Chronic Obstructive Bronchiolitis Obliterans Sepsis Eosinophilic Esophagitis Neonatal Sepsis Rhinitis

Drug Warnings

Black Box Warning
General Warning
Country: United States
Black Box Warning
psychiatric toxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 6 meas. best 8.64
EC50 4 meas. best 5.93
Ki 2 meas. best 5.13

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cysteinyl leukotriene receptor 1
CHEMBL1798
 IC50 8.64 7.575 2.3 2
Streptococcus sp. 'group A'
CHEMBL612389
 EC50 5.93 5.93 1187.0 1
Streptokinase A
CHEMBL1293228
 EC50 5.84 5.655 1436.0 2
G-protein coupled receptor 183
CHEMBL3259470
 IC50 5.25 5.25 5571.0 1
fMet-Leu-Phe receptor
CHEMBL3359
 IC50 5.15 5.15 7029.6 1
Cytochrome P450 2C9
CHEMBL3397
 Ki 5.13 5.13 7400.0 1
Streptococcus
CHEMBL612313
 EC50 5.1 5.1 7956.0 1
Cytochrome P450 2C8
CHEMBL3721
 Ki 4.96 4.96 11000.0 1
Unchecked
CHEMBL612545
 IC50 4.68 4.68 20710.1 1
Cysteinyl leukotriene receptor 2
CHEMBL4330
 IC50 4.57 4.57 27000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.578 mL.min-1.kg-1 Homo sapiens
CL 0.16 ml/min/nmol Homo sapiens
CL 1.8 ml/min/nmol Homo sapiens
CL 0.48 ml/min/nmol Homo sapiens
CL 0.59 ml/min/nmol Homo sapiens
CL 140.0 mL.min-1.g-1 Homo sapiens
Cmax 852.95 nM Homo sapiens
F 60.0 % Homo sapiens
Fu 0.004 - Homo sapiens
Ka 5.18 10^5/M/s Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cysteinyl leukotriene receptor 1 IC50 = 2.3 nM 8.64 Inhibition of cysteinyl leukotriene receptor 1 (unknown origin) expressed in HEK... 28252961
Cysteinyl leukotriene receptor 1 IC50 = 310.0 nM 6.51 Antagonist activity against CysLT1 receptor (unknown origin) expressed in HEK293... 26985325
Streptococcus sp. 'group A' EC50 = 1187.0 nM 5.93 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptokinase A EC50 = 1436.0 nM 5.84 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptokinase A EC50 = 3408.0 nM 5.47 PUBCHEM_BIOASSAY: Absorbance Microorganism-Based Dose Response HTS to Identify I... -
G-protein coupled receptor 183 IC50 = 5571.03 nM 5.25 GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR183 -
fMet-Leu-Phe receptor IC50 = 7029.59 nM 5.15 GPCR PRESTO-Tango dose-response in antagonist mode with target: FPR1 -
Cytochrome P450 2C9 Ki = 7400.0 nM 5.13 Inhibition of recombinant human CYP2C9 expressed in microsomes isolated from bac... 21289076
Streptococcus EC50 = 7956.0 nM 5.1 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Cytochrome P450 2C8 Ki = 11000.0 nM 4.96 Inhibition of recombinant human CYP2C8 expressed in microsomes isolated from bac... 21289076
Unchecked IC50 = 20710.1 nM 4.68 PubChem BioAssay. GLP1 secretion from NCI-H716 cells-IC50. (Class of assay: co... -
Cysteinyl leukotriene receptor 2 IC50 = 27000.0 nM 4.57 Antagonist activity against CysLT2 receptor (unknown origin) expressed in HEK293... 26985325

Literature References

PubMed DOI Target Context # Activities
21289076 10.1124/dmd.110.037689 Liver microsome 18
21289076 10.1124/dmd.110.037689 Cytochrome P450 2C8 11
- 10.6019/CHEMBL4689842 HEK-293T 10
21289076 10.1124/dmd.110.037689 Cytochrome P450 2C9 10
- 10.6019/CHEMBL4689842 U2OS 9
- 10.6019/CHEMBL4689842 Fibroblast 7
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
35227979 10.1016/j.ejmech.2022.114212 Mus musculus 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
21289076 10.1124/dmd.110.037689 Cytochrome P450 3A4 4

Data from ChEMBL 36 via Core Engine