MONTELUKAST

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H36ClNO3S
Molecular Weight	586.183
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(O)C1=C(CC[C@@H](SCC2(CC(O)=O)CC2)C3=CC(\C=C\C4=NC5=CC(Cl)=CC=C5C=C4)=CC=C3)C=CC=C1

InChI

InChIKey=UCHDWCPVSPXUMX-TZIWLTJVSA-N

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

HIDE SMILES / InChI

Molecular Formula	C35H36ClNO3S
Molecular Weight	586.183
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/67093875

Montelukast (SINGULAIR®) is a selective and orally active leukotriene D4 (LTD4) receptor antagonist that inhibits the cysteinyl leukotriene CysLT1 receptor. It is indicated for the prophylaxis and chronic treatment of asthma, for prevention of exercise-induced bronchoconstriction, and for the relief of symptoms of seasonal allergic rhinitis. LTD4 is a product of arachidonic acid metabolism and is released from various cells, including mast cells and eosinophils. This eicosanoid binds to CysLT1 receptor found in the human airway (including airway smooth muscle cells and airway macrophages) and on other pro-inflammatory cells (including eosinophils and certain myeloid stem cells). Cysteinyl leukotriene receptors (CysLTs) have been correlated with the pathophysiology of asthma and allergic rhinitis. In asthma, leukotriene-mediated effects include airway edema, smooth muscle contraction, and altered cellular activity associated with the inflammatory process. In allergic rhinitis, CysLTs are released from the nasal mucosa after allergen exposure during both earlyand late-phase reactions and are associated with symptoms of allergic rhinitis. Montelukast (SINGULAIR®) binds with high affinity and selectivity to the CysLT1 (in preference to other pharmacologically important airway receptors, such as the prostanoid, cholinergic, or beta-adrenergic receptor). It inhibits physiologic actions of LTD4 at the CysLT1 receptor without any agonist activity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cysteinyl leukotriene receptor 1 20 Target ID: CHEMBL1798 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Antagonist 2737		2.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 234 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Primary	Approved 8307	SINGULAIR Approved Use Montelukast sodium tablets are a leukotriene receptor antagonist indicated for: •Prophylaxis and chronic treatment of asthma in patients 2 years of age and older (1.1). •Acute prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older (1.2). •Relief of symptoms of allergic rhinitis (AR): seasonal allergic rhinitis (SAR) in patients 2 years of age and older, and perennial allergic rhinitis (PAR) in patients 2 years of age and older (1.3). 1.1 Asthma Montelukast sodium is indicated for the prophylaxis and chronic treatment of asthma in adults and pediatric patients 2 years of age and older. 1.2 Exercise-Induced Bronchoconstriction (EIB) Montelukast sodium is indicated for prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older. Pediatric use information for patients ages 6 to 14 years of age for acute prevention of exercise-induced bronchoconstriction (EIB) is approved for Merck Sharp & Dohme Corp’s montelukast tablet products. However, due to Merck Sharp & Dohme Corp’s marketing exclusivity rights, this drug product is not labeled with that pediatric information. 1.3 Allergic Rhinitis Montelukast sodium is indicated for the relief of symptoms of seasonal allergic rhinitis in patients 2 years of age and older and perennial allergic rhinitis in patients 2 years of age and older. Launch Date 8.8793278E11
Exercise-induced bronchoconstriction 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Preventing	Approved 8307	SINGULAIR Approved Use Montelukast sodium tablets are a leukotriene receptor antagonist indicated for: •Prophylaxis and chronic treatment of asthma in patients 2 years of age and older (1.1). •Acute prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older (1.2). •Relief of symptoms of allergic rhinitis (AR): seasonal allergic rhinitis (SAR) in patients 2 years of age and older, and perennial allergic rhinitis (PAR) in patients 2 years of age and older (1.3). 1.1 Asthma Montelukast sodium is indicated for the prophylaxis and chronic treatment of asthma in adults and pediatric patients 2 years of age and older. 1.2 Exercise-Induced Bronchoconstriction (EIB) Montelukast sodium is indicated for prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older. Pediatric use information for patients ages 6 to 14 years of age for acute prevention of exercise-induced bronchoconstriction (EIB) is approved for Merck Sharp & Dohme Corp’s montelukast tablet products. However, due to Merck Sharp & Dohme Corp’s marketing exclusivity rights, this drug product is not labeled with that pediatric information. 1.3 Allergic Rhinitis Montelukast sodium is indicated for the relief of symptoms of seasonal allergic rhinitis in patients 2 years of age and older and perennial allergic rhinitis in patients 2 years of age and older. Launch Date 8.8793278E11
Seasonal allergic rhinitis 63 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Primary	Approved 8307	SINGULAIR Approved Use Montelukast sodium tablets are a leukotriene receptor antagonist indicated for: •Prophylaxis and chronic treatment of asthma in patients 2 years of age and older (1.1). •Acute prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older (1.2). •Relief of symptoms of allergic rhinitis (AR): seasonal allergic rhinitis (SAR) in patients 2 years of age and older, and perennial allergic rhinitis (PAR) in patients 2 years of age and older (1.3). 1.1 Asthma Montelukast sodium is indicated for the prophylaxis and chronic treatment of asthma in adults and pediatric patients 2 years of age and older. 1.2 Exercise-Induced Bronchoconstriction (EIB) Montelukast sodium is indicated for prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older. Pediatric use information for patients ages 6 to 14 years of age for acute prevention of exercise-induced bronchoconstriction (EIB) is approved for Merck Sharp & Dohme Corp’s montelukast tablet products. However, due to Merck Sharp & Dohme Corp’s marketing exclusivity rights, this drug product is not labeled with that pediatric information. 1.3 Allergic Rhinitis Montelukast sodium is indicated for the relief of symptoms of seasonal allergic rhinitis in patients 2 years of age and older and perennial allergic rhinitis in patients 2 years of age and older. Launch Date 8.8793278E11
Perennial allergic rhinitis 47 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Primary	Approved 8307	SINGULAIR Approved Use Montelukast sodium tablets are a leukotriene receptor antagonist indicated for: •Prophylaxis and chronic treatment of asthma in patients 2 years of age and older (1.1). •Acute prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older (1.2). •Relief of symptoms of allergic rhinitis (AR): seasonal allergic rhinitis (SAR) in patients 2 years of age and older, and perennial allergic rhinitis (PAR) in patients 2 years of age and older (1.3). 1.1 Asthma Montelukast sodium is indicated for the prophylaxis and chronic treatment of asthma in adults and pediatric patients 2 years of age and older. 1.2 Exercise-Induced Bronchoconstriction (EIB) Montelukast sodium is indicated for prevention of exercise-induced bronchoconstriction (EIB) in patients 15 years of age and older. Pediatric use information for patients ages 6 to 14 years of age for acute prevention of exercise-induced bronchoconstriction (EIB) is approved for Merck Sharp & Dohme Corp’s montelukast tablet products. However, due to Merck Sharp & Dohme Corp’s marketing exclusivity rights, this drug product is not labeled with that pediatric information. 1.3 Allergic Rhinitis Montelukast sodium is indicated for the relief of symptoms of seasonal allergic rhinitis in patients 2 years of age and older and perennial allergic rhinitis in patients 2 years of age and older. Launch Date 8.8793278E11

C_max

Value	Dose	Analyte	Population
541.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9429741/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MONTELUKAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
602.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9429741/	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MONTELUKAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
13.8 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg single, respiratory dose: 1 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
18.5 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg single, respiratory dose: 1 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
224 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg single, respiratory dose: 10 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
23.4 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg 1 times / day multiple, respiratory dose: 1 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
54.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg single, respiratory dose: 3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
184 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg single, respiratory dose: 10 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
225 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg 1 times / day multiple, respiratory dose: 10 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
233 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg single, respiratory dose: 10 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
242 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg 1 times / day multiple, respiratory dose: 10 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
44.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg single, respiratory dose: 3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
5.1 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	0.3 mg single, respiratory dose: 0.3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
5.24 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	0.3 mg single, respiratory dose: 0.3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
60 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg single, respiratory dose: 3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
64.8 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg 1 times / day multiple, respiratory dose: 3 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
76 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg 1 times / day multiple, respiratory dose: 3 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:

AUC

Value	Dose	Analyte	Population
3540 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9429741/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MONTELUKAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3978 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9429741/	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MONTELUKAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
132 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg single, respiratory dose: 1 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
1500 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg single, respiratory dose: 10 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
155 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg single, respiratory dose: 1 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
1576 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg single, respiratory dose: 10 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
1600 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg single, respiratory dose: 10 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
1850 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg 1 times / day multiple, respiratory dose: 10 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
1880 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg 1 times / day multiple, respiratory dose: 10 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
214 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg 1 times / day multiple, respiratory dose: 1 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
357 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg single, respiratory dose: 3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
403 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg single, respiratory dose: 3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
491 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg single, respiratory dose: 3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
526 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg 1 times / day multiple, respiratory dose: 3 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
576 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg 1 times / day multiple, respiratory dose: 3 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:

T_1/2

Value	Dose	Analyte	Population
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9429741/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MONTELUKAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9429741/	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MONTELUKAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.7 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg single, respiratory dose: 1 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
5.7 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg single, respiratory dose: 10 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
8.2 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	1 mg 1 times / day multiple, respiratory dose: 1 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
6.9 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg single, respiratory dose: 3 mg route of administration: respiratory experiment type: single co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
7.4 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg 1 times / day multiple, respiratory dose: 10 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
7.7 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	10 mg 1 times / day multiple, respiratory dose: 10 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
7.6 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg 1 times / day multiple, respiratory dose: 3 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:
8.1 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00636207	3 mg 1 times / day multiple, respiratory dose: 3 mg route of administration: respiratory experiment type: multiple co-administered:	MONTELUKAST plasma	Homo sapiens population: unhealthy age: sex: food status:

Doses

Dose	Population	Adverse events
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8527292	healthy, 21-40 years n = 18 Health Status: healthy Age Group: 21-40 years Sex: M Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/8527292	Sources: https://pubmed.ncbi.nlm.nih.gov/8527292
7 mg single, intravenous Dose: 7 mg Route: intravenous Route: single Dose: 7 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10722763	unhealthy, 29.8 years (range: 15.0–56.0 years) n = 50 Health Status: unhealthy Condition: asthma Age Group: 29.8 years (range: 15.0–56.0 years) Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/10722763	Other AEs: Headache... Other AEs: Headache (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/10722763
80 mg single, oral Overdose Dose: 80 mg Route: oral Route: single Dose: 80 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11931512	unhealthy, 3 years n = 1 Health Status: unhealthy Condition: asthma Age Group: 3 years Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/11931512	Sources: https://pubmed.ncbi.nlm.nih.gov/11931512
200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8828530	unhealthy, 34 years (range: 18-54 years) n = 28 Health Status: unhealthy Condition: chronic asthma Age Group: 34 years (range: 18-54 years) Sex: M+F Population Size: 28 Sources: https://pubmed.ncbi.nlm.nih.gov/8828530	Other AEs: Bilirubin total increased, Alanine aminotransferase increase... Other AEs: Bilirubin total increased (mild, 1 patient) Alanine aminotransferase increase (mild, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8828530
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15069001	unhealthy, 37 years n = 1 Health Status: unhealthy Age Group: 37 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15069001	Disc. AE: Jaundice, Pruritus... AEs leading to discontinuation/dose reduction: Jaundice (1 patient) Pruritus (severe, 1 patient) Nausea (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15069001
1000 ug single, respiratory Dose: 1000 ug Route: respiratory Route: single Dose: 1000 ug Sources: https://pubmed.ncbi.nlm.nih.gov/20936994	unhealthy, 39.1 years (range: 16.0–63.0 years) n = 36 Health Status: unhealthy Condition: chronic asthma Age Group: 39.1 years (range: 16.0–63.0 years) Sex: M+F Population Size: 36 Sources: https://pubmed.ncbi.nlm.nih.gov/20936994	Sources: https://pubmed.ncbi.nlm.nih.gov/20936994
135 mg single, oral Overdose Dose: 135 mg Route: oral Route: single Dose: 135 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11931512	unhealthy, 5 years n = 1 Health Status: unhealthy Condition: asthma Age Group: 5 years Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/11931512	Sources: https://pubmed.ncbi.nlm.nih.gov/11931512
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/20829Orig1s073,20830Orig1s075,21409Orig1s075lbl.pdf	unhealthy, >15 years Health Status: unhealthy Age Group: >15 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/20829Orig1s073,20830Orig1s075,21409Orig1s075lbl.pdf	Other AEs: Psychiatric disorder NOS... Other AEs: Psychiatric disorder NOS (serious) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/20829Orig1s073,20830Orig1s075,21409Orig1s075lbl.pdf

AEs

AE	Significance	Dose	Population
Headache	2%	7 mg single, intravenous Dose: 7 mg Route: intravenous Route: single Dose: 7 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10722763	unhealthy, 29.8 years (range: 15.0–56.0 years) n = 50 Health Status: unhealthy Condition: asthma Age Group: 29.8 years (range: 15.0–56.0 years) Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/10722763
Alanine aminotransferase increase	mild, 1 patient	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8828530	unhealthy, 34 years (range: 18-54 years) n = 28 Health Status: unhealthy Condition: chronic asthma Age Group: 34 years (range: 18-54 years) Sex: M+F Population Size: 28 Sources: https://pubmed.ncbi.nlm.nih.gov/8828530
Bilirubin total increased	mild, 1 patient	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8828530	unhealthy, 34 years (range: 18-54 years) n = 28 Health Status: unhealthy Condition: chronic asthma Age Group: 34 years (range: 18-54 years) Sex: M+F Population Size: 28 Sources: https://pubmed.ncbi.nlm.nih.gov/8828530
Jaundice	1 patient Disc. AE	10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15069001	unhealthy, 37 years n = 1 Health Status: unhealthy Age Group: 37 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15069001
Nausea	1 patient Disc. AE	10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15069001	unhealthy, 37 years n = 1 Health Status: unhealthy Age Group: 37 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15069001
Pruritus	severe, 1 patient Disc. AE	10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15069001	unhealthy, 37 years n = 1 Health Status: unhealthy Age Group: 37 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15069001
Psychiatric disorder NOS	serious	10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/20829Orig1s073,20830Orig1s075,21409Orig1s075lbl.pdf	unhealthy, >15 years Health Status: unhealthy Age Group: >15 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/20829Orig1s073,20830Orig1s075,21409Orig1s075lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50730	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50730
ChemicalBook	CB7112818	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7112818
MolPort	MolPort-006-167-557	https://www.molport.com/shop/molecule-link/MolPort-006-167-557
ZINC	ZINC000003831151	http://zinc15.docking.org/substances/ZINC000003831151

PubMed

Title	Date	PubMed
Pharmacology of leukotriene receptor antagonists.	1998 Jun	9620942
Inhibition of 5-lipoxygenase diminishes neurally evoked tachykinergic contraction of guinea pig isolated airway.	1998 May	9580604
A novel hepatointestinal leukotriene B4 receptor. Cloning and functional characterization.	2000 Dec 29	11006272
The role of LTRAs in the management of persistent asthma.	2000 Sep 15	19681236
The protective effects of leukotriene modifiers in aspirin-induced asthma.	2000 Sep 15	19667532
LTRA inhibition of exercise-induced bronchoconstriction.	2000 Sep 15	19667531
Dose selection and dosing interval determination for LTRA use in asthma.	2000 Sep 15	19667530
Clinical safety and tolerability of montelukast, a leukotriene receptor antagonist, in controlled clinical trials in patients aged > or = 6 years.	2001 Jan	11167954
Long-term asthma control with oral montelukast and inhaled beclomethasone for adults and children 6 years and older.	2001 Jun	11422148
Acute effects of the cys-leukotriene-1 receptor antagonist, montelukast, on experimental colitis in rats.	2001 Oct 19	11698051
Pharmacological differences among CysLT(1) receptor antagonists with respect to LTC(4) and LTD(4) in human lung parenchyma.	2002 Apr 15	11996896
Effects of montelukast and beclomethasone on airway function and asthma control.	2002 Dec	12464949
The cysteinyl-leukotriene D4 induces cytosolic Ca2+ elevation and contraction of the human detrusor muscle.	2003 Aug	12853847
[A study on the heterogeneous apoptosis of lymphocytes, eosinophils, and neutrophils from peripheral blood of asthmatic patients].	2003 Oct	14633444
Montelukast-associated Churg-Strauss syndrome.	2003 Sep	12958007
Montelukast inhibits interleukin-5 mRNA expression and cysteinyl leukotriene production in ragweed and mite-stimulated peripheral blood mononuclear cells from patients with asthma.	2003 Sep-Oct	14619337
Inverse agonist activity of selected ligands of the cysteinyl-leukotriene receptor 1.	2004 Apr	14718577
Montelukast-induced hepatitis.	2004 Apr 6	15069001
Antihistamines added to an antileukotriene in treating seasonal allergic rhinitis: histamine and leukotriene antagonism.	2004 Feb	15061398
Role of leukotriene inhibitors in the postoperative management of nasal polyps.	2005	15925911
Examination of 209 drugs for inhibition of cytochrome P450 2C8.	2005 Jan	15601807
Differential effect of zileuton, a 5-lipoxygenase inhibitor, against nociceptive paradigms in mice and rats.	2005 Jul	15935457
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Influence of leukotriene pathway polymorphisms on response to montelukast in asthma.	2006 Feb 15	16293801
Montelukast and zafirlukast do not affect the pharmacokinetics of the CYP2C8 substrate pioglitazone.	2006 Jul	16670899
Effects of leukotriene receptor antagonists on monocyte chemotaxis, p38 and cytoplasmic calcium.	2006 Jun	16771778
Discovery of biaryl anthranilides as full agonists for the high affinity niacin receptor.	2007 Dec 13	17994679
Prevalence of alpha-1 antitrypsin deficiency in poorly controlled asthma--results from the ALA-ACRC low-dose theophylline trial.	2007 Oct	17943569
CysLTR1 promoter polymorphism and requirement for leukotriene receptor antagonist in aspirin-intolerant asthma patients.	2007 Sep	17924829
Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats.	2007 Sep	17895592
The recently identified P2Y-like receptor GPR17 is a sensor of brain damage and a new target for brain repair.	2008	18974869
Effects of zileuton and montelukast in mouse experimental spinal cord injury.	2008 Feb	18059327
Cysteinyl leukotrienes mediate the enhancing effects of indomethacin and aspirin on eosinophil production in murine bone marrow cultures.	2008 Feb	18037915
Leukotriene D4 increases the excitability of capsaicin-sensitive nasal sensory nerves to electrical and chemical stimuli.	2008 Jul	18500362
Montelukast inhibits tumour necrosis factor-alpha-mediated interleukin-8 expression through inhibition of nuclear factor-kappaB p65-associated histone acetyltransferase activity.	2008 May	18325031
Pharmacological modulation of leukotriene D(4) attenuates the development of opioid dependence in a mouse model of naloxone-induced opioid withdrawal syndrome.	2008 Nov 19	18840427
Cysteinyl leucotriene receptor type 1 mediates contraction in human and guinea-pig oesophagus.	2008 Oct	18651869
Montelukast-associated Churg-Strauss vasculitis: another associated report.	2009 Apr	19441609
Discovery of novel tricyclic full agonists for the G-protein-coupled niacin receptor 109A with minimized flushing in rats.	2009 Apr 23	19309152
Montelukast is a potent and durable inhibitor of multidrug resistance protein 2-mediated efflux of taxol and saquinavir.	2009 Dec	19952419
Functional expression, inhibition and induction of CYP enzymes in HepaRG cells.	2009 Jun	19328226
Leukotriene pathways and in vitro adenotonsillar cell proliferation in children with obstructive sleep apnea.	2009 May	19118273
Enhanced fracture repair by leukotriene antagonism is characterized by increased chondrocyte proliferation and early bone formation: a novel role of the cysteinyl LT-1 receptor.	2009 Oct	19544365
Concentration-dependent noncysteinyl leukotriene type 1 receptor-mediated inhibitory activity of leukotriene receptor antagonists.	2010 Feb 15	20083671
Comparative study of the oxidation of propranolol enantiomers in hepatic and small intestinal microsomes from cynomolgus and marmoset monkeys.	2010 Jan 5	19853591
Antileukotriene drugs in the treatment of asthma.	2010 Mar	20332717
5-Lipoxygenase-activating protein (FLAP) inhibitors. Part 4: development of 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor.	2011 Dec 8	22059882
Association of the variants in AGT gene with modified drug response in Korean aspirin-intolerant asthma patients.	2011 Oct	21624492
Identification of old drugs as potential inhibitors of HIV-1 integrase - human LEDGF/p75 interaction via molecular docking.	2012 Dec	22733274
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

Patents

Sample Use Guides

In Vivo Use Guide

SINGULAIR® should be taken once daily in the evening. The following dose is recommended for adults and adolescents 15 years of age and older: one 10-mg tablet.

Route of Administration: Oral

In Vitro Use Guide

Montelukast is a potent and selective inhibitor of [3H]leukotriene D4 specific binding in guinea pig lung (Ki 0.18 +/- 0.03 nM), sheep lung (Ki 4 nM), and dimethylsulfoxide-differentiated U937 cell plasma membrane preparations (Ki 0.52 +/- 0.23 nM), but it was essentially inactive versus [3H]leukotriene C4 specific binding in dimethylsulfoxide-differentiated U937 cell membranes (IC50 10 microM) and [3H]leukotriene B4 specific binding in THP-1 cell membranes (IC50 40 microM). Montelukast also inhibited specific binding of [3H]leukotriene D4 to guinea pig lung in the presence of human serum albumin, human plasma, and squirrel monkey plasma with Ki values of 0.21 +/- 0.08, 0.19 +/- 0.02, and 0.26 +/- 0.02 nM, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 18:14:14 UTC 2022` Edited by `admin` on `Fri Dec 16 18:14:14 UTC 2022`
Record UNII	MHM278SD3E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MONTELUKAST

Official Name

English

MONTELUKAST [MI]

Common Name

English

montelukast [INN]

Common Name

English

MONTELUKAST [VANDF]

Common Name

English

BRONDILAT

Brand Name

English

(1-((((1R)-1-(3-((E)-2-(7-CHLOROQUINOLIN-2-YL)VINYL)PHENYL)-3-(2-(1-HYDROXY-1-METHYLETHYL)PHENYL)PROPYL)THIO)METHYL)CYCLOPROPYL)ACETIC ACID

Systematic Name

English

Montelukast [WHO-DD]

Common Name

English

CYCLOPROPANEACETIC ACID, 1-((((1R)-1-(3-((E)-2-(7-CHLORO-2-QUINOLINYL)ETHENYL)PHENYL)-3-(2-(1-HYDROXY-1-METHYLETHYL)PHENYL)PROPYL)THIO)METHYL)-

Common Name

English

MONTELUKAST [HSDB]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000000083