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Compound Detail

CHEMBL21333

PRANLUKAST
💊 Approved Drug
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💊 Approved Drug
O=C(Nc1cccc2c(=O)cc(-c3nnn[nH]3)oc12)c1ccc(OCCCCc2ccccc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL21333
Name PRANLUKAST
Phase Approved
Structure Type MOL
InChI Key NBQKINXMPLXUET-UHFFFAOYSA-N

Known Names

Azlaire CCN 00401 CCN-00401 ONO 1078 ONO-1078 Onon Pranlukast RS 411 RS-411 SB 205312 SB-205312
12
Targets
25
Activities
4
Assay Types
2
PK Parameters
20
Publications
11
Known Names
3
Indications
1
Mechanisms

Molecular Properties

481.5
MW (Da)
4.63
ALogP
7
HBA
2
HBD
123.0
PSA (Ų)
0.29
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Unknown
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -ast

Extended Properties

Molecular Formula C27H23N5O4
MW 481.51
Aromatic Rings 5
Heavy Atoms 36
NP-Likeness -0.89

Mechanism of Action

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

Indications

Lung Diseases, Obstructive Rhinitis, Allergic, Seasonal Sinusitis

ATC Classification

R03DC02
pranlukast
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

IC50 15 meas. best 10.36
Ki 6 meas. best 9.1
EC50 2 meas. best 4.82
Kd 2 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cysteinyl leukotriene receptor
CHEMBL2094254
 IC50 10.36 10.36 0.0 1
Cysteinyl leukotriene receptor 1
CHEMBL5645
 IC50 10.36 9.68 0.0 2
Cysteinyl leukotriene receptor 1
CHEMBL1798
 IC50 9.1 8.55 0.8 4
Cysteinyl leukotriene receptor
CHEMBL2094254
 Ki 9.1 9.1 0.8 1
Cysteinyl leukotriene receptor 1
CHEMBL5645
 Ki 9.1 9.1 0.8 2
Cysteinyl leukotriene receptor
CHEMBL2094254
 Kd 9.0 9.0 1.0 1
Homo sapiens
CHEMBL372
 IC50 9.0 9.0 1.0 1
U-937
CHEMBL612794
 IC50 9.0 9.0 1.0 2
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.57 5.57 2700.0 1
Bile salt export pump
CHEMBL6020
 IC50 5.53 5.53 2970.0 1
Cysteinyl leukotriene receptor 2
CHEMBL4330
 IC50 5.44 5.44 3620.0 1
Uracil nucleotide/cysteinyl leukotriene receptor
CHEMBL1075162
 Ki 5.39 5.39 4060.0 1
Cruzipain
CHEMBL3563
 IC50 5.16 4.665 7000.0 2
Bile acid receptor
CHEMBL2047
 EC50 4.82 4.82 15000.0 2
ATP-binding cassette sub-family C member 2
CHEMBL2073676
 Ki 4.39 4.39 41100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4192.03 ng.hr.mL-1 Homo sapiens
T1/2 9.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cysteinyl leukotriene receptor IC50 = 0.044 nM 10.36 Inhibition of LTC4 induced smooth muscle contraction of guinea pig ileum 3336036
Cysteinyl leukotriene receptor 1 IC50 = 0.044 nM 10.36 Displacement of [3H]ICI from cysteinyl leukotriene receptor 1 in Hartley guinea ... 28252961
Cysteinyl leukotriene receptor 1 Ki = 0.8 nM 9.1 In vitro binding of Cysteinyl leukotriene receptor 1 to guinea pig lung membrane... 10509933
Cysteinyl leukotriene receptor 1 IC50 = 0.8 nM 9.1 Antagonist activity at CysLT1 receptor in human dU937 cells assessed as inhibiti... 20621485
Cysteinyl leukotriene receptor Ki = 0.8 nM 9.1 Ability to antagonize LTD4 receptors isolated from guinea pig lung membranes 9873435
Cysteinyl leukotriene receptor 1 Ki = 0.8 nM 9.1 Antagonism of Cysteinyl leukotriene receptor 1 from guinea pig lung membranes 9934474
U-937 IC50 = 1.0 nM 9.0 Compound was evaluated for influx of calcium mobilization in human U937 cells 9873435
Cysteinyl leukotriene receptor 1 IC50 = 1.0 nM 9.0 Binding affinity towards Cysteinyl leukotriene D4 receptor (cysLT1) was measured... 9554877
U-937 IC50 = 1.0 nM 9.0 In vitro blocking of extracellular calcium mobilization in human U937 cells 10509933
Homo sapiens IC50 = 1.0 nM 9.0 Compound was tested for its ability to inhibit calcium influx in human U937 cell... 9934474
Cysteinyl leukotriene receptor Kd = 1.0 nM 9.0 Displacement of [3H]LTD4 from Cysteinyl leukotriene D4 receptor in guinea pig lu... 9089329
Cysteinyl leukotriene receptor 1 IC50 = 4.3 nM 8.37 Antagonist activity at human CysLT1 receptor 34767347
Cysteinyl leukotriene receptor 1 IC50 = 4.3 nM 8.37 Antagonist activity at human CysLT1 26200813
Cysteinyl leukotriene receptor 1 IC50 = 4.4 nM 8.36 Inhibition of cysteinyl leukotriene receptor 1 (unknown origin) expressed in HEK... 28252961
ATP-binding cassette sub-family C member 4 IC50 = 2700.0 nM 5.57 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Bile salt export pump IC50 = 2970.0 nM 5.53 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Cysteinyl leukotriene receptor 2 IC50 = 3620.0 nM 5.44 Antagonist activity at human CysLT2 expressed in HEK293T cells assessed as inhib... 26200813
Uracil nucleotide/cysteinyl leukotriene receptor Ki = 4060.0 nM 5.39 Displacement of [3H]PSB-12150 from human GPR17 expressed in CHO-K1 cell membrane... 24900835
Cruzipain IC50 = 7000.0 nM 5.16 Inhibition of Trypanosoma cruzi cruzaine preincubated for 5 mins before substrat... 20426472
Bile acid receptor EC50 = 15000.0 nM 4.82 Agonist activity at FXR (unknown origin) 34889100

Literature References

PubMed DOI Target Context # Activities
31188588 10.1021/acs.jmedchem.9b00428 Unchecked 22
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
- 10.6019/CHEMBL4689842 HEK-293T 10
31188588 10.1021/acs.jmedchem.9b00428 N-acetylgalactosamine-6-sulfatase 10
- 10.6019/CHEMBL4689842 Fibroblast 10
- 10.6019/CHEMBL4689842 U2OS 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3336036 10.1021/jm00396a013 Cavia porcellus 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5

Data from ChEMBL 36 via Core Engine