MONTELUKAST, CIS-

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=CC=CC=C1CC[C@@H](SCC2(CC(O)=O)CC2)C3=CC=CC(\C=C/C4=NC5=CC(Cl)=CC=C5C=C4)=C3

InChI

InChIKey=UCHDWCPVSPXUMX-LNMNGANESA-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

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 2778		2.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 241 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Primary	Approved 8429	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 1998
Exercise-induced bronchoconstriction 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Preventing	Approved 8429	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 1998
Seasonal allergic rhinitis 64 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Primary	Approved 8429	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 1998
Perennial allergic rhinitis 47 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020829s069,020830s071,021409s047lbl.pdf	Primary	Approved 8429	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 1998

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
Montelukast added to inhaled beclomethasone in treatment of asthma. Montelukast/Beclomethasone Additivity Group.	1999 Dec	10588598
Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor.	1999 Sep	10462554
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
The cysteinyl-leukotriene D4 induces cytosolic Ca2+ elevation and contraction of the human detrusor muscle.	2003 Aug	12853847
Montelukast-induced hepatitis.	2004 Apr 6	15069001
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
Prevalence of alpha-1 antitrypsin deficiency in poorly controlled asthma--results from the ALA-ACRC low-dose theophylline trial.	2007 Oct	17943569
Cysteinyl leukotrienes mediate the enhancing effects of indomethacin and aspirin on eosinophil production in murine bone marrow cultures.	2008 Feb	18037915
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
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
Comparative study of the oxidation of propranolol enantiomers in hepatic and small intestinal microsomes from cynomolgus and marmoset monkeys.	2010 Jan 5	19853591
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.

Name

Type

Language

MONTELUKAST, CIS-

Common Name

English

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

Systematic Name

English

MONTELUKAST SODIUM IMPURITY, CIS-ISOMER- [USP IMPURITY]

Common Name

English

(1-((((1R)-1-(3-((Z)-2-(7-CHLOROQUINOLIN-2-YL)ETHENYL)PHENYL)-3-(2-(1-HYDROXY-1-METHYLETHYL)PHENYL)PROPYL)SULFANYL)METHYL)CYCLOPROPYL)ACETIC ACID

Systematic Name

English

MONTELUKAST SODIUM IMPURITY G [EP IMPURITY]

Common Name

English

Code System Code Type Description

CAS

774538-96-4

Created by admin on Sat Dec 16 09:57:52 GMT 2023 , Edited by admin on Sat Dec 16 09:57:52 GMT 2023

PRIMARY

FDA UNII

O71E8P3Y4C

Created by admin on Sat Dec 16 09:57:52 GMT 2023 , Edited by admin on Sat Dec 16 09:57:52 GMT 2023

PRIMARY

PUBCHEM

57345775

Created by admin on Sat Dec 16 09:57:52 GMT 2023 , Edited by admin on Sat Dec 16 09:57:52 GMT 2023

PRIMARY

SUBSTANCE RECORD


					O71E8P3Y4C

MONTELUKAST, CIS-

Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2