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

Similar Structures

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

Poor quality drug data slowing you down?

Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.

Download eBook

Poor quality drug data slowing you down?

Download eBook

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 older^4,5 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 older^4,5; 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 older^4,5.

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

Reduce drug development failure rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Associated Conditions

Indication Type	Indication	Approval Level	Patient Characteristics
Prevention of	Asthma	••••••••••••
Management of	Asthma	••••••••••••
Prevention of	Exercise-induced bronchoconstriction	••••••••••••
Management of	Perennial allergic rhinitis	••••••••••••	•••••••••• •••••••• •• •••••••••••• •••••••
Management of	Seasonal allergic rhinitis	••••••••••••	•••••••••• •••••••• •• •••••••••••• •••••••

Contraindications & Blackbox Warnings

Prevent Adverse Drug Events Today

Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events with our Clinical API

Learn more

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}

Target	Actions	Organism
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

Montelukast

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

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!

See the data

Improve decision support & research outcomes with our structured adverse effects data.

See a data sample

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

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Drug	Interaction
Integrate drug-drug interactions in your software
Abametapir	The serum concentration of Montelukast can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Montelukast can be increased when combined with Abatacept.
Abiraterone	The metabolism of Montelukast can be decreased when combined with Abiraterone.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Montelukast.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Montelukast.

Food Interactions

Take with or without food. The absorption is unaffected by food.

Products

Drug product information from 10+ global regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

Access now

Access drug product information from over 10 global regions.

Access now

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Montelukast sodium	U1O3J18SFL	151767-02-1	LBFBRXGCXUHRJY-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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
M-montelukast	Tablet, chewable	5 mg	Oral	Mantra Pharma Inc	Not applicable	Not applicable
M-montelukast	Tablet, chewable	4 mg	Oral	Mantra Pharma Inc	Not applicable	Not applicable
M-montelukast	Tablet	10 mg	Oral	Mantra Pharma Inc	2019-12-13	Not applicable
Montelukast	Tablet	10 mg	Oral	Sivem Pharmaceuticals Ulc	2012-06-10	Not applicable
Montelukast	Tablet, chewable	4 mg	Oral	Sanis Health Inc	2012-03-21	2020-01-02

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Accel-montelukast Sodium Tablets	Tablet	10 mg	Oral	Accel Pharma Inc	Not applicable	Not applicable
Ach-montelukast	Tablet	10 mg	Oral	Accord Healthcare Inc	2012-03-28	Not applicable
Ach-montelukast	Tablet, chewable	5 mg	Oral	Accord Healthcare Inc	2014-06-09	2017-08-07
Ach-montelukast	Tablet, chewable	4 mg	Oral	Accord Healthcare Inc	2014-06-09	2017-08-07
Ag-montelukast	Tablet, chewable	5 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
AIRCOMB 2,5 MG/4 MG GRANÜL İÇEREN SAŞE, 30 ADET	Montelukast sodium (4 mg) + Desloratadine (2.5 mg)	Granule		NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AIRCOMB 2,5 MG/4 MG GRANÜL İÇEREN SAŞE, 90 ADET	Montelukast sodium (4 mg) + Desloratadine (2.5 mg)	Granule		NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AIRCOMB 5/10 MG FILM KAPLI TABLET, 30 ADET	Montelukast (10 mg) + Desloratadine (5 mg)	Tablet, coated	Oral	CELTİS İLAÇ SAN. VE TİC. A.Ş.	2011-03-04	Not applicable
AIRCOMB 5/10 MG FILM KAPLI TABLET, 90 ADET	Montelukast (10 mg) + Desloratadine (5 mg)	Tablet, coated	Oral	CELTİS İLAÇ SAN. VE TİC. A.Ş.	2011-03-04	Not applicable
AIRPASS 5/10 MG FILM KAPLI TABLET, 30 ADET	Montelukast (10 mg) + Levocetirizine dihydrochloride (5 mg)	Tablet, coated	Oral	CELTİS İLAÇ SAN. VE TİC. A.Ş.	2011-02-23	Not applicable

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

Falk NP, Hughes SW, Rodgers BC: Medications for Chronic Asthma. Am Fam Physician. 2016 Sep 15;94(6):454-62. [Article]
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]
Singulair (montelukast sodium) US FDA Label 2019 [Link]
Apo-Montelukast Canadian Product Monograph [Link]
Electronic Medicines Compendium: Montelukast 10 mg Film Coated Tablets Monograph [Link]
NCBI StatPearls [Internet]: Montelukast Profile [Link]
Electronic Medicines Compendium: Montelukast 4mg Chewable Tablets Monograph [Link]
Montelukast sodium tablets and chewable tablets Canadian Product Monograph [Link]
Electronic Medicines Compendium: Montelukast 5 mg Chewable Tablets Monograph [Link]
FDA Approved Drug Products: SINGULAIR (montelukast) oral tablets and granules [Link]

External Links

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);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Bronchiolitis Acute	1
4	Completed	Not Available	Asthma	2
4	Completed	Basic Science	Asthma	1
4	Completed	Diagnostic	Asthmatic Smokers / Non-asthmatic Smokers	1
4	Completed	Diagnostic	Cough	1

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

Form	Route	Strength
Tablet, film coated	Oral	10.00 mg
Granule
Tablet, chewable	Oral	5.2 mg
Tablet	Oral	5 mg
Tablet, chewable	Oral	4 mg
Tablet	Oral	10.380 mg
Tablet	Oral	10 MG
Tablet, chewable	Buccal	5 mg
Tablet, coated	Oral
Tablet	Oral	4 mg
Tablet, film coated	Oral
Tablet, coated	Oral
Granule	Oral	4.160 mg
Tablet	Oral	10.40 mg
Tablet	Oral	5.000 mg
Capsule	Oral
Tablet, chewable	Oral	500000 mg
Tablet, chewable	Oral
Powder	Oral
Tablet	Oral
Granule	Oral	4 mg
Tablet, soluble	Oral	4 mg
Tablet	Oral	5.00 mg
Tablet	Oral	10.000 mg
Tablet, chewable	Oral	4.000 mg
Tablet, chewable	Oral	5 mg
Tablet	Oral	5.188 mg
Tablet	Oral
Tablet, coated	Oral	1000000 mg
Tablet, chewable	Buccal	4 mg
Tablet, chewable	Buccal	400000 mg
Tablet, chewable	Oral	400000 mg
Tablet, chewable	Oral	5.187 mg
Tablet, film coated	Oral
Tablet, chewable	Oral
Tablet, chewable	Oral	4.00 mg
Tablet, chewable	Oral	5.00 mg
Granule	Oral
Granule	Oral	4.0 mg
Granule	Oral	4 mg/1
Granule	Oral	4 mg/500mg
Tablet	Oral	10 mg/1
Tablet, coated	Oral	10 mg/1
Tablet, chewable	Oral	10 mg
Tablet, chewable	Oral	4.15 mg
Tablet	Oral	4.000 mg
Tablet	Oral	10.400 mg
Tablet	Oral	5.0 mg
Capsule, liquid filled	Oral
Tablet, coated	Oral	10 mg
Film, soluble	Oral	4157 Mg
Tablet	Oral	10.00 mg
Granule	Oral	10 mg/1
Granule	Oral	4 mg / sachet
Granule	Oral	4.000 mg
Granule	Oral	5 mg/1
Tablet, chewable	Oral	4 mg/1
Tablet, chewable	Oral	4.16 MG
Tablet, chewable	Oral	5 mg/1
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	10.4 MG
Granule	Oral	4 mg/1sachet
Tablet, film coated	Oral	4 mg
Tablet	Oral	5.200 mg
Granule	Oral
Tablet	Oral	4.150 mg
Capsule, liquid filled	Oral	10 mg
Tablet, film coated	Oral	10 mg

Prices

Unit description	Cost	Unit
Singulair 30 4 mg Chew Tabs Bottle	145.91USD	bottle
Singulair 30 4 mg Packets Packet	145.91USD	packet
Singulair 30 5 mg Chew Tabs Bottle	145.91USD	bottle
Singulair 10 mg tablet	4.77USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
CA2179407	No	2009-03-17	2014-12-22
CA2053209	No	1998-12-08	2011-10-10
US8007830	No	2011-08-30	2022-10-24

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	275.9 F	msds
water solubility	mixes with water (>100 mg/ml, 25 C)	msds
logP	7.9	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	8.2e-06 mg/mL	ALOGPS
logP	7.25	ALOGPS
logP	8.49	Chemaxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	4.4	Chemaxon
pKa (Strongest Basic)	3.12	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	70.42 Å²	Chemaxon
Rotatable Bond Count	12	Chemaxon
Refractivity	169.5 m³·mol^-1	Chemaxon
Polarizability	66.36 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9947
Blood Brain Barrier	+	0.9311
Caco-2 permeable	+	0.5428
P-glycoprotein substrate	Substrate	0.6839
P-glycoprotein inhibitor I	Non-inhibitor	0.8863
P-glycoprotein inhibitor II	Non-inhibitor	0.9154
Renal organic cation transporter	Non-inhibitor	0.8395
CYP450 2C9 substrate	Non-substrate	0.6967
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.7284
CYP450 1A2 substrate	Non-inhibitor	0.6266
CYP450 2C9 inhibitor	Non-inhibitor	0.7177
CYP450 2D6 inhibitor	Non-inhibitor	0.8436
CYP450 2C19 inhibitor	Non-inhibitor	0.5777
CYP450 3A4 inhibitor	Non-inhibitor	0.6759
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5515
Ames test	Non AMES toxic	0.7532
Carcinogenicity	Non-carcinogens	0.9126
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.6488 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.985
hERG inhibition (predictor II)	Non-inhibitor	0.7932

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-002f-8200940000-737f7d3443710f11b1d1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014s-0300390000-119eee6ed8a35756d986
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00e9-1000190000-3ae1972df1eef120bacb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0fk9-2003960000-cddb9d6b9c81a1a5812c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0uk9-1200920000-9c59fb036334a4ca02f8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ugi-5400930000-048bec43950675ca14f1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-1311930000-500d924395be9dd1781e

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[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

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	72	N/A	N/A	A28303
IC 50 (nM)	0.5	N/A	N/A	A28299
IC 50 (nM)	0.78	N/A	N/A	A28301
Ki (nM)	0.5	N/A	N/A	A28300
Ki (nM)	2.1	N/A	N/A	A28302

Details1. Cysteinyl leukotriene receptor 1

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

Nayak A: A review of montelukast in the treatment of asthma and allergic rhinitis. Expert Opin Pharmacother. 2004 Mar;5(3):679-86. [Article]
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]
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]
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]
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]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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]
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]
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]
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]
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]
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]

Details2. Arachidonate 5-lipoxygenase

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

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

Details1. Prostaglandin G/H synthase 1

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

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]

Details2. Cytochrome P450 2A6

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

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]

Details3. Cytochrome P450 3A4

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

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]

Details4. Cytochrome P450 2C9

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

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]
Montelukast FDA label [File]

Details5. Cytochrome P450 2C8

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

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]
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]
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]
Flockhart Table of Drug Interactions [Link]
Singulair (montelukast sodium) US FDA Label 2019 [Link]

Transporters

Details1. Solute carrier organic anion transporter family member 2B1

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

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

Montelukast

Identification

Structure for Montelukast (DB00471)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

Enzymes

References

References

References

References

References

Transporters

References