U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of MONTELUKAST, (S)-

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-OYLFJNDKSA-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-/m0/s1

HIDE SMILES / InChI
MONTELUKAST, (S)- is a Montelukast impurity A. Montelukast is a leukotriene receptor antagonist (LTRA) used for the maintenance treatment of asthma and to relieve symptoms of seasonal allergies. Montelukast sodium possesses one chiral carbon center, and a racemic form of montelukast sodium contains equal amounts of the two enantiomeric forms, i.e., the S and R optical isomers. The biologically active form of montelukast sodium is the R stereoisomer. Since the biological activity of the two enantiomers can be different, it is imperative that the amount of the S stereoisomer in the commercial product be controlled to within acceptable limits. The amount of the S optical isomer of montelukast should be lower than 0.15%

Originator

Curator's Comment: # Merck & Co.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
MONTELUKAST, (S)-
Common Name English
MONTELUKAST SODIUM IMPURITY A [EP IMPURITY]
Common Name English
(1-((((1S)-1-(3-((E)-2-(7-CHLOROQUINOLIN-2-YL)ETHENYL)PHENYL)-3-(2-(1-HYDROXY-1-METHYLETHYL)PHENYL)PROPYL)SULFANYL)METHYL)CYCLOPROPYL)ACETIC ACID
Systematic Name English
CYCLOPROPANEACETIC ACID, 1-((((1S)-1-(3-((1E)-2-(7-CHLORO-2-QUINOLINYL)ETHENYL)PHENYL)-3-(2-(1-HYDROXY-1-METHYLETHYL)PHENYL)PROPYL)THIO)METHYL)-
Systematic Name English
Code System Code Type Description
CAS
220927-27-5
Created by admin on Sat Dec 16 09:57:53 GMT 2023 , Edited by admin on Sat Dec 16 09:57:53 GMT 2023
PRIMARY
PUBCHEM
6540473
Created by admin on Sat Dec 16 09:57:53 GMT 2023 , Edited by admin on Sat Dec 16 09:57:53 GMT 2023
PRIMARY
FDA UNII
H28ST60VMZ
Created by admin on Sat Dec 16 09:57:53 GMT 2023 , Edited by admin on Sat Dec 16 09:57:53 GMT 2023
PRIMARY