Identification

Name
Montelukast
Accession Number
DB00471  (APRD00434)
Type
Small Molecule
Groups
Approved
Description

Montelukast is a leukotriene receptor antagonist (LTRA) used for the maintenance treatment of asthma and to relieve symptoms of seasonal allergies. It is usually administered orally. Montelukast blocks the action of leukotriene D4 on the cysteinyl leukotriene receptor CysLT1 in the lungs and bronchial tubes by binding to it. This reduces the bronchoconstriction otherwise caused by the leukotriene, and results in less inflammation. Because of its method of operation, it is not useful for the treatment of acute asthma attacks. Again because of its very specific locus of operation, it does not interact with other allergy medications such as theophylline. Montelukast is marketed in United States and many other countries by Merck & Co. with the brand name Singulair®. It is available as oral tablets, chewable tablets, and oral granules. In India and other countries, it is also marketed under the brand name Montair®, produced by Indian company Cipla.

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
MontelukastTablet, chewable5 mgOralSanis Health Inc2012-03-21Not applicableCanada
MontelukastTablet10 mgOralPro Doc Limitee2012-03-29Not applicableCanada
MontelukastTablet, chewable5 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
MontelukastTablet, chewable4 mgOralSanis Health Inc2012-03-21Not applicableCanada
MontelukastTablet, chewable5 mgOralPro Doc Limitee2012-03-29Not applicableCanada
MontelukastTablet, chewable4 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
MontelukastTablet10 mgOralSanis Health Inc2012-03-21Not applicableCanada
MontelukastTablet10 mgOralRanbaxy Inc.Not applicableNot applicableCanada
MontelukastTablet, chewable4 mgOralPro Doc Limitee2012-03-29Not applicableCanada
MontelukastTablet10 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
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
Apo-montelukastTablet, chewable4 mgOralApotex Corporation2013-02-15Not applicableCanada
Apo-montelukastTablet, chewable5 mgOralApotex Corporation2013-02-15Not applicableCanada
Apo-montelukastTablet10 mgOralApotex Corporation2012-01-20Not applicableCanada
Auro-montelukastTablet10 mgOralAuro Pharma Inc2013-03-04Not applicableCanada
Auro-montelukast Chewable TabletTablet, chewable5 mgOralAuro Pharma Inc2014-03-26Not applicableCanada
Auro-montelukast Chewable TabletTablet, chewable4 mgOralAuro Pharma Inc2014-03-26Not applicableCanada
Bio-montelukastTablet10 mgOralBiomed PharmaNot applicableNot applicableCanada
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

For the treatment of asthma

Associated Conditions
Pharmacodynamics

Montelukast, like zafirlukast, is a leukotriene receptor antagonist used as an alternative to anti-inflammatory medications in the management and chronic treatment of asthma and exercise-induced bronchospasm (EIB). Unlike zafirlukast, montelukast does not inhibit CYP2C9 or CYP3A4 and is, therefore, not expected to affect the hepatic clearance of drugs metabolized by these enzymes.

Mechanism of action

Montelukast selectively antagonizes leukotriene D4 (LTD4) at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Montelukast inhibits the actions of LTD4 at the CysLT1 receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.

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

Rapidly absorbed following oral administration (bioavailability is 64%)

Volume of distribution
  • 8 to 11 L
Protein binding

99% (to plasma proteins)

Metabolism

Hepatic

Route of elimination

Coupled with estimates of montelukast oral bioavailability, this indicates that montelukast and its metabolites are excreted almost exclusively via the bile.

Half life

2.7-5.5 hours

Clearance
  • 45 mL/min [healthy adults]
Toxicity

Side effects include headache, abdominal or stomach pain, cough, dental pain, dizziness, fever, heartburn, skin rash, stuffy nose, weakness or unusual tiredness.

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.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone 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.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Montelukast.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Montelukast.
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
Not Available
External Links
Human Metabolome Database
HMDB0014614
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
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Montelukast
ATC Codes
R03DC53 — Montelukast, combinationsR03DC03 — Montelukast
AHFS Codes
  • 48:10.24 — Leukotriene Modifiers
PDB Entries
2nni
FDA label
Download (503 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 Volunteers4
1CompletedBasic ScienceChronic Lung Disease of Prematurity1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceRheumatoid Arthritis2
1CompletedDiagnosticAsthma Bronchial1
1CompletedDiagnosticAsthma, Exercise-Induced1
1CompletedOtherAsthma Bronchial2
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
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
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)3
3CompletedTreatmentRhinitis, Allergic, Perennial1
3CompletedTreatmentRhinitis, Allergic, Seasonal2
3CompletedTreatmentSeasonal Allergic Rhinitis (SAR)7
3CompletedTreatmentWheezing1
3Not Yet RecruitingTreatmentSleep Apnea, Obstructive1
3RecruitingTreatmentPain1
3Unknown StatusPreventionUpper Respiratory Tract Infections1
3Unknown StatusTreatmentBronchial Asthma1
3WithdrawnTreatmentBronchial Asthma1
4Active Not RecruitingTreatmentAsthma Bronchial1
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 Bronchial18
4CompletedTreatmentAsthma Bronchial / Asthma, Exercise-Induced1
4CompletedTreatmentAsthma Bronchial / Atopic Dermatitis (AD) / Conjunctivitis, Seasonal Allergic / Seasonal Allergic Rhinitis (SAR)1
4CompletedTreatmentAsthma Bronchial / Seasonal Allergic Rhinoconjunctivitis1
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
Tablet, chewableOral5 mg/1
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
US8007830No2002-10-242022-10-24Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
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
Human
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
Human
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
Human
Pharmacological action
Unknown
Actions
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]
Kind
Protein
Organism
Human
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
Human
Pharmacological action
Unknown
Actions
Substrate
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. 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
Human
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
Human
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
Human
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 October 16, 2018 08:27