Montelukast

Identification

Summary

Montelukast is a leukotriene receptor antagonist used as part of an asthma therapy regimen, to prevent exercise induced bronchoconstriction, and to treat seasonal allergic rhinitis.

Brand Names
Singulair
Generic Name
Montelukast
DrugBank Accession Number
DB00471
Background

Montelukast was first approved for clinical use by the US FDA in 1998 as Merck's brand name Singulair.3 The medication is a member of the leukotriene receptor antagonist (LTRA) category of drugs.3,4,5,6,7,8,9 Although capable of demonstrating effectiveness, the use of such LTRAs like montelukast is typically in addition to or complementary with the use of inhaled corticosteroids or other agents in asthma step therapy.1 Regardless, in 2008-2009, there were FDA-led investigations into the possibility of montelukast to elicit neuropsychiatric effects like agitation, hallucinations, suicidal behaviour, and others in individuals who used the medication.2 And although these kinds of effects are currently included in the official prescribing information for montelukast,3,4,5,6,7,8,9 the drug still sees extensive use worldwide via millions of prescriptions annually and has since become available as a generic and as a brand name product.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 586.183
Monoisotopic: 585.21044242
Chemical Formula
C35H36ClNO3S
Synonyms
  • (R-(E))-1-(((1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid
  • 1-[[[(1 R)-1-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulfanyl]methyl]cyclopropaneacetic acid
  • Montelukast
  • Montélukast
  • Montelukastum
External IDs
  • L 706631
  • MK 0476
  • MK 476

Pharmacology

Indication

Montelukast is indicated for:

(a) the prophylaxis and chronic treatment of asthma in adults and pediatric patients who are 12 months of age and older3, although other regional health authorities specifically note this indication for adults and adolescents who are 15 years and older4,5 and also include indications for preventing day and night-time symptoms, and the treatment of acetylsalicylic acid-sensitive asthma4;

(b) the prevention of exercise-induced bronchoconstriction (EIB) in patients who are 6 years of age and older3, although other regional health authorities specifically note this indication for adults and adolescents who are 15 years and older4,5; and

(c) the relief of symptoms of seasonal allergic rhinitis in patients 2 years of age and older and perennial allergic rhinitis in patients 6 months of age and older3, although other regional health authorities specifically note the relief of seasonal allergic rhinitis symptoms for adults and adolescents who are 15 years and older4,5.

Furthermore, some formulations like chewable montelukast tablets may also be specifically indicated by particular regulatory bodies for the prophylaxis and chronic treatment of asthma, including the prevention of day and night-time symptoms, the treatment of acetylsalicylic acid based asthma, and the prevention of exercise-induced bronchoconstriction in adult and pediatric patients aged 2 and older8, between the ages 2 and 57, or between the ages of 6 and 14 years.9

Moreover, when employed for such indications montelukast is considered effective as monotherapy or when combined with other medications indicated for the maintenance treatment of chronic asthma.4,8 For instance, montelukast and inhaled corticosteroids can be used concomitantly to demonstrate additive effects to control asthma or to decrease the necessary inhaled corticosteroid dose while still maintaining clinical stability.4,8

Additionally, in patients who continue to experience asthma symptoms, montelukast can also be combined with an 'as required' short-acting beta-agonist, an inhaled corticosteroid, or inhaled corticosteroid paired with a long-acting beta-agonist.4,8

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prevention ofAsthma••••••••••••
Management ofAsthma••••••••••••
Prevention ofExercise-induced bronchoconstriction••••••••••••
Management ofPerennial allergic rhinitis•••••••••••••••••••••• •••••••• •• •••••••••••• •••••••
Management ofSeasonal allergic rhinitis•••••••••••••••••••••• •••••••• •• •••••••••••• •••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Montelukast is a leukotriene receptor antagonist that demonstrates a marked affinity and selectivity to the cysteinyl leukotriene receptor type-1 in preference to many other crucial airway receptors like the prostanoid, cholinergic, or beta-adrenergic receptors.3,4,5,6,7,8,9 As a consequence, the agent can elicit substantial blockage of LTD4 leukotriene-mediated bronchoconstriction with doses as low as 5 mg.3,4,5,6,7,8,9 Moreover, a placebo-controlled, crossover study (n=12) demonstrated that montelukast is capable of inhibiting early and late phase bronchoconstriction caused by antigen challenge by 75% and 57% respectively.3,4,5,6,7,8,9

In particular, it has been documented that montelukast can cause bronchodilation as soon as within 2 hours of oral administration.3,4,5,6,7,8,9 This action can also be additive to the bronchodilation caused by the concomitant use of a beta agonist.3,4,5,6,7,8,9 Nevertheless, clinical investigations performed with adults 15 years of age and older revealed that no additional clinical benefit is obtained when doses of montelukast greater than 10 mg a day are used.3,4,5,6,7,8,9

Additionally, in clinical trials with adults and pediatric asthmatic patients aged 6 to 14 years, it was also determined that montelukast can reduce mean peripheral blood eosinophils by about 13% to 15% from baseline in comparison to placebo during double-blind treatment periods.3,4,5,6,7,8,9 At the same time, in patients aged 15 years and older who were experiencing seasonal allergic rhinitis, the use of montelukast caused a median reduction of 13% in peripheral blood eosinophil counts when compared to placebo as well.3,4,5,6,7,8,9

Mechanism of action

Cysteinyl leukotrienes (CysLT) like LTC4, LTD4, and LTE4, among others, are eicosanoids released by a variety of cells like mast cells and eosinophils.3,4,5,6,7,8,9 When such CysLT bind to corresponding CysLT receptors like CysLT type-1 receptors located on respiratory airway smooth muscle cells, airway macrophages, and on various pro-inflammatory cells like eosinophils and some specific myeloid stem cells activities that facilitate the pathophysiology of asthma and allergic rhinitis are stimulated.3,4,5,6,7,8,9

In particular, CysLT-mediated airway bronchoconstriction, occluding mucous secretion, vascular permeability, and eosinophil recruitment are all types of effects that facilitate asthma.3,4,5,6,7,8,9 Alternatively, in allergic rhinitis, CysLTs are released by the nasal mucosa when exposed to allergens during both early and late phase reactions and participate in eliciting symptoms of allergic rhinitis like a congested nose and airway.3,4,5,6,7,8,9

Subsequently, montelukast is a leukotriene receptor antagonist that binds with high affinity and selectivity to the CysLT type 1 receptor, which consequently assists in inhibiting any physiological actions of CysLTs like LTC4, LTD4, and LTE4 at the receptor that may facilitate asthma or allergic rhinitis.3,4,5,6,7,8,9

TargetActionsOrganism
ACysteinyl leukotriene receptor 1
antagonist
Humans
UArachidonate 5-lipoxygenase
other/unknown
Humans
Absorption

It has been observed that montelukast is quickly absorbed following administration by the oral route.3,4,5,6,7,8,9 The oral bioavailability documented for the drug is 64%.3,4,5,6,7,8,9 Furthermore, it seems that having a regular meal in the morning or even a high fat snack in the evening does not affect the absorption of montelukast.3,4,5,6,7,8,9

Volume of distribution

The steady-state volume of distribution recorded for montelukast is an average between 8 to 11 litres.3,4,5,7,8,9

Protein binding

It has been determined that the protein binding of montelukast to plasma proteins exceeds 99%.3,4,5,7,8,9

Metabolism

It has been determined that montelukast is highly metabolized and typically so by the cytochrome P450 3A4, 2C8, and 2C9 isoenzymes.3,4,5,6,7,8,9 In particular, it seems that the CYP2C8 enzymes play a significant role in the metabolism of the drug.3,4,5,6,7,8,9 Nevertheless, at therapeutic doses, the plasma concentrations of montelukast metabolites are undetectable at steady state in adults and pediatric patients.3,4,5,6,7,8,9

Hover over products below to view reaction partners

Route of elimination

It has been reported that montelukast and its metabolites are almost exclusively excreted in the bile and into the feces.3,4,5,6,7,8,9

Half-life

Studies have demonstrated that the mean plasma half-life of montelukast varies from 2.7 to 5.5 hours when observed in healthy young adults.3,4,5,7,8,9

Clearance

The plasma clearance documented for montelukast is an average of 45 mL/min when observed in healthy adults.3,4,5,7,8,9

Adverse Effects
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Toxicity

The adverse effects associated with overdosage of montelukast include abdominal pain, somnolence, thirst, headache, vomiting, psychomotor hyperactivity, and less frequently, convulsion.3,4,5,6,7,8,9

The oral LD50 value determined for mice and rats is >5000 mg/kg.3,4,5,6,7,8,9

Montelukast has not been studied in pregnant women.3,4,5,6,7,8,9 Consequently, it should be used during pregnancy only if clearly needed.3,4,5,6,7,8,9

Additionally, as it is unknown whether montelukast is excreted into human breast milk, there is also caution regarding the use of the medication in nursing mothers.3,4,5,6,7,8,9

The plasma half-life of montelukast is somewhat prolonged in elderly patients, although no dosage adjustment is generally necessary.3,4,5,6,7,8,9

Pathways
Not Available
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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Montelukast can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Montelukast can be increased when combined with Abatacept.
AbirateroneThe metabolism of Montelukast can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Montelukast.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Montelukast.
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Montelukast sodiumU1O3J18SFL151767-02-1LBFBRXGCXUHRJY-HKHDRNBDSA-M
Product Images
International/Other Brands
Lukotas / Molly (Allenge) / Monocast (Beximco) / Monteflo / Montelo-10 / Montene (Square) / Respaire (Santa-Farma) / Surfair (Sandoz) / Telumantes (Actavis) / Ventek (Searle) / Ventilar (Gutis) / Xalar (Unimed) / Zespira (Bilim)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
M-montelukastTablet, chewable5 mgOralMantra Pharma IncNot applicableNot applicableCanada flag
M-montelukastTablet, chewable4 mgOralMantra Pharma IncNot applicableNot applicableCanada flag
M-montelukastTablet10 mgOralMantra Pharma Inc2019-12-13Not applicableCanada flag
MontelukastTablet10 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada flag
MontelukastTablet, chewable4 mgOralSanis Health Inc2012-03-212020-01-02Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-montelukast Sodium TabletsTablet10 mgOralAccel Pharma IncNot applicableNot applicableCanada flag
Ach-montelukastTablet10 mgOralAccord Healthcare Inc2012-03-28Not applicableCanada flag
Ach-montelukastTablet, chewable5 mgOralAccord Healthcare Inc2014-06-092017-08-07Canada flag
Ach-montelukastTablet, chewable4 mgOralAccord Healthcare Inc2014-06-092017-08-07Canada flag
Ag-montelukastTablet, chewable5 mgOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AIRCOMB 2,5 MG/4 MG GRANÜL İÇEREN SAŞE, 30 ADETMontelukast sodium (4 mg) + Desloratadine (2.5 mg)GranuleNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
AIRCOMB 2,5 MG/4 MG GRANÜL İÇEREN SAŞE, 90 ADETMontelukast sodium (4 mg) + Desloratadine (2.5 mg)GranuleNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
AIRCOMB 5/10 MG FILM KAPLI TABLET, 30 ADETMontelukast (10 mg) + Desloratadine (5 mg)Tablet, coatedOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2011-03-04Not applicableTurkey flag
AIRCOMB 5/10 MG FILM KAPLI TABLET, 90 ADETMontelukast (10 mg) + Desloratadine (5 mg)Tablet, coatedOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2011-03-04Not applicableTurkey flag
AIRPASS 5/10 MG FILM KAPLI TABLET, 30 ADETMontelukast (10 mg) + Levocetirizine dihydrochloride (5 mg)Tablet, coatedOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2011-02-23Not applicableTurkey flag

Categories

ATC Codes
R03DC03 — MontelukastR03DC53 — Montelukast, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as linear 1,3-diarylpropanoids. These are organic compounds with a structure based on a C6-C3-C6 skeleton, where the two benzene rings are not linked together.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Linear 1,3-diarylpropanoids
Sub Class
Not Available
Direct Parent
Linear 1,3-diarylpropanoids
Alternative Parents
Chloroquinolines / Phenylpropanes / Styrenes / Thia fatty acids / Hydroxy fatty acids / Pyridines and derivatives / Aryl chlorides / Tertiary alcohols / Heteroaromatic compounds / Sulfenyl compounds
show 11 more
Substituents
Alcohol / Aromatic alcohol / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolines, monocarboxylic acid, aliphatic sulfide (CHEBI:50730)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
MHM278SD3E
CAS number
158966-92-8
InChI Key
UCHDWCPVSPXUMX-TZIWLTJVSA-N
InChI
InChI=1S/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/b15-10+/t32-/m1/s1
IUPAC Name
2-[1-({[(1R)-1-{3-[(1E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
SMILES
OC(=O)CC1(CC1)CS[C@H](CCC1=CC=CC=C1C(O)(C)C)C1=CC=CC(\C=C\C2=NC3=C(C=CC(Cl)=C3)C=C2)=C1

References

Synthesis Reference

Evgeny Shapiro, Ronit Yahalomi, Valerie Niddam-Hildesheim, Greta Sterimbaum, Kobi Chen, "Processes for preparing montelukast sodium." U.S. Patent US20050256156, issued November 17, 2005.

US20050256156
General References
  1. Falk NP, Hughes SW, Rodgers BC: Medications for Chronic Asthma. Am Fam Physician. 2016 Sep 15;94(6):454-62. [Article]
  2. Lu CY, Zhang F, Lakoma MD, Butler MG, Fung V, Larkin EK, Kharbanda EO, Vollmer WM, Lieu T, Soumerai SB, Chen Wu A: Asthma Treatments and Mental Health Visits After a Food and Drug Administration Label Change for Leukotriene Inhibitors. Clin Ther. 2015 Jun 1;37(6):1280-91. doi: 10.1016/j.clinthera.2015.03.027. Epub 2015 Apr 25. [Article]
  3. Singulair (montelukast sodium) US FDA Label 2019 [Link]
  4. Apo-Montelukast Canadian Product Monograph [Link]
  5. Electronic Medicines Compendium: Montelukast 10 mg Film Coated Tablets Monograph [Link]
  6. NCBI StatPearls [Internet]: Montelukast Profile [Link]
  7. Electronic Medicines Compendium: Montelukast 4mg Chewable Tablets Monograph [Link]
  8. Montelukast sodium tablets and chewable tablets Canadian Product Monograph [Link]
  9. Electronic Medicines Compendium: Montelukast 5 mg Chewable Tablets Monograph [Link]
  10. FDA Approved Drug Products: SINGULAIR (montelukast) oral tablets and granules [Link]
Human Metabolome Database
HMDB0014614
KEGG Drug
D08229
KEGG Compound
C07482
PubChem Compound
5281040
PubChem Substance
46505585
ChemSpider
4444507
BindingDB
50052024
RxNav
88249
ChEBI
50730
ChEMBL
CHEMBL787
ZINC
ZINC000003831151
Therapeutic Targets Database
DAP000309
PharmGKB
PA450546
PDBe Ligand
MTK
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Montelukast
PDB Entries
2nni
FDA label
Download (503 KB)
MSDS
Download (331 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentBronchiolitis Acute1
4CompletedNot AvailableAsthma2
4CompletedBasic ScienceAsthma1
4CompletedDiagnosticAsthmatic Smokers / Non-asthmatic Smokers1
4CompletedDiagnosticCough1

Pharmacoeconomics

Manufacturers
  • Merck research laboratories div merck co inc
  • Merck and co inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Apotheca Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Lake Erie Medical and Surgical Supply
  • Merck & Co.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Tya Pharmaceuticals
  • Vangard Labs Inc.
Dosage Forms
FormRouteStrength
Tablet, film coatedOral10.00 mg
Granule
Tablet, chewableOral5.2 mg
TabletOral5 mg
Tablet, chewableOral4 mg
TabletOral10.380 mg
TabletOral10 MG
Tablet, chewableBuccal5 mg
Tablet, coatedOral
TabletOral4 mg
Tablet, film coatedOral
Tablet, coatedOral
GranuleOral4.160 mg
TabletOral10.40 mg
TabletOral5.000 mg
CapsuleOral
Tablet, chewableOral500000 mg
Tablet, chewableOral
PowderOral
TabletOral
GranuleOral4 mg
Tablet, solubleOral4 mg
TabletOral5.00 mg
TabletOral10.000 mg
Tablet, chewableOral4.000 mg
Tablet, chewableOral5 mg
TabletOral5.188 mg
TabletOral
Tablet, coatedOral1000000 mg
Tablet, chewableBuccal4 mg
Tablet, chewableBuccal400000 mg
Tablet, chewableOral400000 mg
Tablet, chewableOral5.187 mg
Tablet, film coatedOral
Tablet, chewableOral
Tablet, chewableOral4.00 mg
Tablet, chewableOral5.00 mg
GranuleOral
GranuleOral4.0 mg
GranuleOral4 mg/1
GranuleOral4 mg/500mg
TabletOral10 mg/1
Tablet, coatedOral10 mg/1
Tablet, chewableOral10 mg
Tablet, chewableOral4.15 mg
TabletOral4.000 mg
TabletOral10.400 mg
TabletOral5.0 mg
Capsule, liquid filledOral
Tablet, coatedOral10 mg
Film, solubleOral4157 Mg
TabletOral10.00 mg
GranuleOral10 mg/1
GranuleOral4 mg / sachet
GranuleOral4.000 mg
GranuleOral5 mg/1
Tablet, chewableOral4 mg/1
Tablet, chewableOral4.16 MG
Tablet, chewableOral5 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral10.4 MG
GranuleOral4 mg/1sachet
Tablet, film coatedOral4 mg
TabletOral5.200 mg
GranuleOral
TabletOral4.150 mg
Capsule, liquid filledOral10 mg
Tablet, film coatedOral10 mg
Prices
Unit descriptionCostUnit
Singulair 30 4 mg Chew Tabs Bottle145.91USD bottle
Singulair 30 4 mg Packets Packet145.91USD packet
Singulair 30 5 mg Chew Tabs Bottle145.91USD bottle
Singulair 10 mg tablet4.77USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2179407No2009-03-172014-12-22Canada flag
CA2053209No1998-12-082011-10-10Canada flag
US8007830No2011-08-302022-10-24US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)275.9 Fmsds
water solubilitymixes with water (>100 mg/ml, 25 C)msds
logP7.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.2e-06 mg/mLALOGPS
logP7.25ALOGPS
logP8.49Chemaxon
logS-7.8ALOGPS
pKa (Strongest Acidic)4.4Chemaxon
pKa (Strongest Basic)3.12Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area70.42 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity169.5 m3·mol-1Chemaxon
Polarizability66.36 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9947
Blood Brain Barrier+0.9311
Caco-2 permeable+0.5428
P-glycoprotein substrateSubstrate0.6839
P-glycoprotein inhibitor INon-inhibitor0.8863
P-glycoprotein inhibitor IINon-inhibitor0.9154
Renal organic cation transporterNon-inhibitor0.8395
CYP450 2C9 substrateNon-substrate0.6967
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7284
CYP450 1A2 substrateNon-inhibitor0.6266
CYP450 2C9 inhibitorNon-inhibitor0.7177
CYP450 2D6 inhibitorNon-inhibitor0.8436
CYP450 2C19 inhibitorNon-inhibitor0.5777
CYP450 3A4 inhibitorNon-inhibitor0.6759
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5515
Ames testNon AMES toxic0.7532
CarcinogenicityNon-carcinogens0.9126
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6488 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.985
hERG inhibition (predictor II)Non-inhibitor0.7932
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002f-8200940000-737f7d3443710f11b1d1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014s-0300390000-119eee6ed8a35756d986
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-1000190000-3ae1972df1eef120bacb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-2003960000-cddb9d6b9c81a1a5812c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uk9-1200920000-9c59fb036334a4ca02f8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ugi-5400930000-048bec43950675ca14f1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1311930000-500d924395be9dd1781e
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-255.3040083
predicted
DarkChem Lite v0.1.0
[M-H]-229.65105
predicted
DeepCCS 1.0 (2019)
[M+H]+255.6608083
predicted
DarkChem Lite v0.1.0
[M+H]+231.50833
predicted
DeepCCS 1.0 (2019)
[M+Na]+254.9365083
predicted
DarkChem Lite v0.1.0
[M+Na]+237.21309
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Leukotriene receptor activity
Specific Function
Receptor for cysteinyl leukotrienes mediating bronchoconstriction of individuals with and without asthma. Stimulation by LTD4 results in the contraction and proliferation of smooth muscle, edema, e...
Gene Name
CYSLTR1
Uniprot ID
Q9Y271
Uniprot Name
Cysteinyl leukotriene receptor 1
Molecular Weight
38540.55 Da
References
  1. Nayak A: A review of montelukast in the treatment of asthma and allergic rhinitis. Expert Opin Pharmacother. 2004 Mar;5(3):679-86. [Article]
  2. Zhang YJ, Zhang L, Wang SB, Shen HH, Wei EQ: Montelukast modulates lung CysLT(1) receptor expression and eosinophilic inflammation in asthmatic mice. Acta Pharmacol Sin. 2004 Oct;25(10):1341-6. [Article]
  3. Hamacher J, Eichert K, Braun C, Grebe T, Strub A, Lucas R, Eltze M, Wendel A: Montelukast exerts no acute direct effect on NO synthases. Pulm Pharmacol Ther. 2007;20(5):525-33. Epub 2006 May 19. [Article]
  4. Langlois A, Ferland C, Tremblay GM, Laviolette M: Montelukast regulates eosinophil protease activity through a leukotriene-independent mechanism. J Allergy Clin Immunol. 2006 Jul;118(1):113-9. Epub 2006 May 19. [Article]
  5. Alfieri AB, Tramontana M, Cialdai C, Lecci A, Giuliani S, Crea A, Manzini S, Maggi CA: Heterogeneous effect of leucotriene CysLT1 receptor antagonists on antigen-induced motor and inflammatory responses in guinea-pig airways. Auton Autacoid Pharmacol. 2007 Jan;27(1):39-46. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. Singh RK, Tandon R, Dastidar SG, Ray A: A review on leukotrienes and their receptors with reference to asthma. J Asthma. 2013 Nov;50(9):922-31. doi: 10.3109/02770903.2013.823447. Epub 2013 Aug 16. [Article]
  8. Amrani Y, Moore PE, Hoffman R, Shore SA, Panettieri RA Jr: Interferon-gamma modulates cysteinyl leukotriene receptor-1 expression and function in human airway myocytes. Am J Respir Crit Care Med. 2001 Dec 1;164(11):2098-101. doi: 10.1164/ajrccm.164.11.2108005. [Article]
  9. Wei J, Chen S, Guo W, Feng B, Yang S, Huang C, Chu J: Leukotriene D4 induces cellular senescence in osteoblasts. Int Immunopharmacol. 2018 May;58:154-159. doi: 10.1016/j.intimp.2017.12.027. Epub 2018 Mar 26. [Article]
  10. Zhang Z, Luo J, Huang J, Liu Z, Fang S, Zhang WP, Wei E, Lu Y: [Leukotriene D4 activates BV2 microglia in vitro]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2013 May;42(3):253-60. [Article]
  11. Reques FG, Rodriguez JL: Tolerability of leukotriene modifiers in asthma: a review of clinical experience. BioDrugs. 1999 Jun;11(6):385-94. doi: 10.2165/00063030-199911060-00003. [Article]
  12. Lamoureux J, Stankova J, Rola-Pleszczynski M: Leukotriene D4 enhances immunoglobulin production in CD40-activated human B lymphocytes. J Allergy Clin Immunol. 2006 Apr;117(4):924-30. doi: 10.1016/j.jaci.2005.12.1329. Epub 2006 Feb 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Iron ion binding
Specific Function
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name
ALOX5
Uniprot ID
P09917
Uniprot Name
Arachidonate 5-lipoxygenase
Molecular Weight
77982.595 Da
References
  1. Ramires R, Caiaffa MF, Tursi A, Haeggstrom JZ, Macchia L: Novel inhibitory effect on 5-lipoxygenase activity by the anti-asthma drug montelukast. Biochem Biophys Res Commun. 2004 Nov 12;324(2):815-21. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
This enzyme effect is supported only by data from in vitro studies.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Cardoso Jde O, Oliveira RV, Lu JB, Desta Z: In Vitro Metabolism of Montelukast by Cytochrome P450s and UDP-Glucuronosyltransferases. Drug Metab Dispos. 2015 Dec;43(12):1905-16. doi: 10.1124/dmd.115.065763. [Article]
  2. Montelukast FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Schoch GA, Yano JK, Sansen S, Dansette PM, Stout CD, Johnson EF: Determinants of cytochrome P450 2C8 substrate binding: structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J Biol Chem. 2008 Jun 20;283(25):17227-37. doi: 10.1074/jbc.M802180200. Epub 2008 Apr 15. [Article]
  2. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [Article]
  3. Walsky RL, Obach RS, Gaman EA, Gleeson JP, Proctor WR: Selective inhibition of human cytochrome P4502C8 by montelukast. Drug Metab Dispos. 2005 Mar;33(3):413-8. doi: 10.1124/dmd.104.002766. Epub 2004 Dec 17. [Article]
  4. Flockhart Table of Drug Interactions [Link]
  5. Singulair (montelukast sodium) US FDA Label 2019 [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Mougey EB, Feng H, Castro M, Irvin CG, Lima JJ: Absorption of montelukast is transporter mediated: a common variant of OATP2B1 is associated with reduced plasma concentrations and poor response. Pharmacogenet Genomics. 2009 Feb;19(2):129-38. doi: 10.1097/FPC.0b013e32831bd98c. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55