Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Montelukast
Accession Number
DB00471  (APRD00434)
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Montelukast sodiumU1O3J18SFL151767-02-1LBFBRXGCXUHRJY-HKHDRNBDSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
M-montelukastTablet, chewable4 mgOralMantra Pharma IncNot applicableNot applicableCanada
M-montelukastTablet10 mgOralMantra Pharma IncNot applicableNot applicableCanada
M-montelukastTablet, chewable5 mgOralMantra Pharma IncNot applicableNot applicableCanada
MontelukastTablet, chewable4 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
MontelukastTablet10 mgOralRanbaxy Inc.Not applicableNot applicableCanada
MontelukastTablet, chewable4 mgOralPro Doc Limitee2012-03-29Not applicableCanada
MontelukastTablet10 mgOralPro Doc Limitee2012-03-29Not applicableCanada
MontelukastTablet10 mgOralSanis Health Inc2012-03-21Not applicableCanada
MontelukastTablet, chewable5 mgOralPro Doc Limitee2012-03-29Not applicableCanada
MontelukastTablet10 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-montelukast Sodium TabletsTablet10 mgOralAccel Pharma IncNot applicableNot applicableCanada
Ach-montelukastTablet, chewable5 mgOralAccord Healthcare Limited2014-06-09Not applicableCanada
Ach-montelukastTablet, chewable4 mgOralAccord Healthcare Limited2014-06-09Not applicableCanada
Ag-montelukastTablet, chewable4 mgOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-montelukastTablet10 mgOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-montelukastTablet, chewable5 mgOralAngita Pharma Inc.Not applicableNot applicableCanada
Apo-montelukastTablet10 mgOralApotex Corporation2012-01-20Not applicableCanada
Apo-montelukastTablet, chewable5 mgOralApotex Corporation2013-02-15Not applicableCanada
Apo-montelukastTablet, chewable4 mgOralApotex Corporation2013-02-15Not applicableCanada
Auro-montelukastTablet10 mgOralAuro Pharma Inc2013-03-04Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
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)
Categories
UNII
MHM278SD3E
CAS number
158966-92-8
Weight
Average: 586.183
Monoisotopic: 585.21044242
Chemical Formula
C35H36ClNO3S
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-[(E)-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

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

Associated Conditions
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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

Learn more
Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more
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

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

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Montelukast.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Montelukast.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Montelukast.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Montelukast.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Montelukast.
6-Deoxyerythronolide BThe metabolism of Montelukast can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Montelukast.
7-ethyl-10-hydroxycamptothecinThe metabolism of Montelukast can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Montelukast.
AbataceptThe metabolism of Montelukast can be increased when combined with Abatacept.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Take without regard to meals.

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. [PubMed:27637121]
  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. [PubMed:25920571]
  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]
External Links
Human Metabolome Database
HMDB0014614
KEGG Drug
D08229
KEGG Compound
C07482
PubChem Compound
5281040
PubChem Substance
46505585
ChemSpider
4444507
BindingDB
50052024
ChEBI
50730
ChEMBL
CHEMBL787
Therapeutic Targets Database
DAP000309
PharmGKB
PA450546
HET
MTK
Wikipedia
Montelukast
ATC Codes
R03DC03 — MontelukastR03DC53 — Montelukast, combinations
AHFS Codes
  • 48:10.24 — Leukotriene Modifiers
PDB Entries
2nni
FDA label
Download (503 KB)
MSDS
Download (331 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAsthma Bronchial4
1Active Not RecruitingTreatmentMultiple Myeloma (MM)1
1CompletedNot AvailableAsthma and Allergic Rhinitis1
1CompletedNot AvailableDrug-drug Interaction Study1
1CompletedNot AvailableHealthy Volunteers3
1CompletedBasic ScienceChronic Lung Disease of Prematurity1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceRheumatoid Arthritis2
1CompletedDiagnosticAsthma Bronchial1
1CompletedDiagnosticAsthma, Exercise-Induced1
1CompletedOtherAsthma Bronchial2
1CompletedOtherHealthy Adults1
1CompletedOtherHealthy Volunteers1
1CompletedOtherHealthy Volunteers / Rheumatoid Arthritis1
1CompletedTreatmentAsthma Bronchial4
1CompletedTreatmentChronic Asthma1
1CompletedTreatmentHealthy Volunteers7
1CompletedTreatmentOesophagitis, Eosinophilic1
1CompletedTreatmentRhinitis1
1Unknown StatusBasic ScienceAsthma Bronchial1
1, 2RecruitingTreatmentDisseminated Sclerosis1
2Active Not RecruitingTreatmentPremature Labour1
2CompletedPreventionChronic Lung Disease of Prematurity / Premature Births / Very Low Birth Weight Infant1
2CompletedTreatmentAllergic Rhinitis (AR)1
2CompletedTreatmentAsthma Bronchial16
2CompletedTreatmentAsthma Bronchial / Rhinitis, Allergic, Seasonal1
2CompletedTreatmentBronchiolitis1
2CompletedTreatmentChronic Graft Versus Host Disease / Hematopoietic Stem Cell Transplant (HSCT) / Leukotriene / Montelukast / Obliterative Bronchiolitis1
2CompletedTreatmentObliterative Bronchiolitis1
2Not Yet RecruitingTreatmentAcute Asthma Exacerbation / Asthma Acute / Asthma Attack / Asthma Bronchial / Asthma in Children / Asthma; Status1
2Not Yet RecruitingTreatmentAlzheimer's Disease (AD)1
2TerminatedPreventionCryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Obliterative Bronchiolitis / Respiratory Tract Infections (RTI)1
2TerminatedTreatmentAsthma Bronchial1
2TerminatedTreatmentSleep Apnea Syndrome1
2Unknown StatusTreatmentAsthma Bronchial1
2Unknown StatusTreatmentCoughing1
2WithdrawnTreatmentAsthma Bronchial1
2, 3CompletedPreventionAsthma Bronchial / Chronic Lung Diseases1
2, 3Unknown StatusTreatmentAsthma Bronchial1
2, 3Unknown StatusTreatmentAsthma Bronchial / Status Asthmaticus2
2, 3WithdrawnTreatmentAsthma Bronchial1
3Active Not RecruitingTreatmentOesophagitis, Eosinophilic / Swallowing Disorders1
3CompletedPreventionAsthma, Exercise-Induced3
3CompletedTreatmentAllergic Rhinitis (AR)1
3CompletedTreatmentAsthma Bronchial21
3CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentAsthma Bronchial / Wheezing1
3CompletedTreatmentAsthma in Children1
3CompletedTreatmentBronchial Asthma1
3CompletedTreatmentBronchiolitis1
3CompletedTreatmentExercised Induced Asthma1
3CompletedTreatmentObstructive Sleep Apnea (OSA)1
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)3
3CompletedTreatmentRhinitis, Allergic, Perennial1
3CompletedTreatmentRhinitis, Allergic, Seasonal2
3CompletedTreatmentSeasonal Allergic Rhinitis (SAR)7
3CompletedTreatmentWheezing1
3RecruitingTreatmentPain NOS1
3RecruitingTreatmentRheumatoid Arthritis1
3RecruitingTreatmentSleep Apnea, Obstructive1
3Unknown StatusPreventionUpper Respiratory Tract Infections1
3Unknown StatusTreatmentBronchial Asthma1
3WithdrawnTreatmentBronchial Asthma1
4CompletedNot AvailableAsthma Bronchial2
4CompletedBasic ScienceAsthma Bronchial1
4CompletedDiagnosticAsthmatic Smokers / Non-asthmatic Smokers1
4CompletedDiagnosticCoughing1
4CompletedPreventionAcute Otitis Media / Ear Infection / Otitis Media (OM)1
4CompletedPreventionAirway Reactivity1
4CompletedPreventionExercise Induced Bronchospasm1
4CompletedPreventionUpper Respiratory Infections1
4CompletedSupportive CareAsthma Bronchial1
4CompletedTreatmentAcute Asthma Exacerbation1
4CompletedTreatmentAcute Wheezy Bronchitis / Asthma Acute1
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentAllergic Rhinitis (AR) / Asthma Bronchial1
4CompletedTreatmentAsthma Bronchial19
4CompletedTreatmentAsthma Bronchial / Asthma, Exercise-Induced1
4CompletedTreatmentAsthma Bronchial / Atopic Dermatitis (AD) / Conjunctivitis, Seasonal Allergic / Seasonal Allergic Rhinitis (SAR)1
4CompletedTreatmentAtopic Dermatitis (AD)1
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentBronchial Hyperreactivity / Coughing1
4CompletedTreatmentCoughing1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentElderly / Persistent Asthma1
4CompletedTreatmentExercise-Induced Bronchoconstriction (EIB)1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentLung Diseases, Obstructive / Signs and Symptoms, Respiratory1
4CompletedTreatmentObliterative Bronchiolitis / Rejection, Transplant / Transplantation, Lung1
4CompletedTreatmentObstructive Sleep Apnea Syndrome (OSAS)1
4CompletedTreatmentPerennial Allergic Rhinitis (PAR)1
4CompletedTreatmentPeriodontitis, Chronic1
4CompletedTreatmentRhinitis, Allergic, Seasonal1
4Not Yet RecruitingTreatmentAsthma and Allergic Rhinitis1
4Not Yet RecruitingTreatmentAtopic Dermatitis (AD)1
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentCoughing1
4TerminatedDiagnosticAsthma Bronchial1
4TerminatedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease1
4TerminatedTreatmentAsthma Bronchial1
4TerminatedTreatmentObstructive Sleep Apnea (OSA)1
4TerminatedTreatmentRhinitis, Allergic, Perennial1
4Unknown StatusTreatmentAsthma Bronchial1
4Unknown StatusTreatmentAsthma Bronchial / Polyps, Nasal / Sinusitis1
4Unknown StatusTreatmentBronchial Asthma / Children / Food Allergy1
4Unknown StatusTreatmentNonasthmatic Eosinophilic Bronchitis1
4Unknown StatusTreatmentPersistent Cough / Whooping Cough1
4Unknown StatusTreatmentRhinitis1
4Unknown StatusTreatmentSeasonal Allergic Rhinitis (SAR)1
4Unknown StatusTreatmentSleep Disordered Breathing (SDB)1
4Unknown StatusTreatmentWheezing1
Not AvailableCompletedNot AvailableAsthma Bronchial3
Not AvailableCompletedBasic ScienceAirway Inflammation1
Not AvailableCompletedBasic ScienceNasal Allergies1
Not AvailableCompletedDiagnosticBronchial Asthma1
Not AvailableCompletedPreventionAsthma Bronchial1
Not AvailableCompletedPreventionMild Persistent Asthma / Rhinitis, Allergic, Perennial1
Not AvailableCompletedTreatmentAsthma Bronchial3
Not AvailableCompletedTreatmentAsthma Bronchial / BMI >30 kg/m2 / Inflammatory Reaction1
Not AvailableCompletedTreatmentAsthma Bronchial / Chronic Lung Diseases1
Not AvailableCompletedTreatmentAsthma, Allergic1
Not AvailableCompletedTreatmentAtopic Dermatitis (AD)1
Not AvailableCompletedTreatmentBronchiolitis2
Not AvailableCompletedTreatmentBronchiolitis / Coughing / Wheezing1
Not AvailableCompletedTreatmentCoronary Heart Disease (CHD)1
Not AvailableCompletedTreatmentEosinophilic Gastroenteritis / Indigestion1
Not AvailableCompletedTreatmentRenal Insufficiency,Chronic1
Not AvailableRecruitingNot AvailableAsthma Bronchial1
Not AvailableRecruitingNot AvailableBronchiolitis Obliterans Syndrome (BOS)1
Not AvailableRecruitingNot AvailablePortal Vein, Cavernous Transformation Of1
Not AvailableTerminatedTreatmentAsthmatic Patients1
Not AvailableTerminatedTreatmentOesophagitis, Eosinophilic1
Not AvailableUnknown StatusBasic ScienceAsthma Bronchial1
Not AvailableUnknown StatusTreatmentChronic Otitis Media With Effusion / Conductive Hearing Loss1
Not AvailableUnknown StatusTreatmentCoughing1
Not AvailableUnknown StatusTreatmentStatus Asthmaticus1

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
GranuleOral4 mg/1
GranuleOral4 mg/500mg
TabletOral10 mg/1
Tablet, coatedOral10 mg/1
GranuleOral10 mg/1
GranuleOral4 mg
GranuleOral5 mg/1
TabletOral10 mg
Tablet, chewableOral4 mg/1
Tablet, chewableOral4 mg
Tablet, chewableOral5 mg/1
Tablet, chewableOral5 mg
Tablet, film coatedOral10 mg/1
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)
CA2179407No2009-03-172014-12-22Canada
CA2053209No1998-12-082011-10-10Canada
US8007830No2011-08-302022-10-24Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Linear 1,3-diarylpropanoid / Haloquinoline / Chloroquinoline / Quinoline / Phenylpropane / Styrene / Hydroxy fatty acid / Thia fatty acid / Aryl chloride / Aryl halide
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolines, monocarboxylic acid, aliphatic sulfide (CHEBI:50730)

Targets

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. [PubMed:15013935]
  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. [PubMed:15456537]
  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. [PubMed:16815057]
  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. [PubMed:16815146]
  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. [PubMed:17199874]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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. [PubMed:15474500]

Enzymes

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. [PubMed:18413310]
  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. [PubMed:15601807]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  4. 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. [PubMed:15608135]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  6. Singulair (montelukast sodium) US FDA Label 2019 [Link]
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. [PubMed:19515014]
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. [PubMed:26374173]
  2. Montelukast FDA label [File]
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. [PubMed:19515014]
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. [PubMed:19515014]

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. [PubMed:19151602]

Drug created on June 13, 2005 07:24 / Updated on July 16, 2019 06:23