MTK

MONTELUKAST

Created: 2006-10-26
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count77
Chiral Atom Count1
Bond Count81
Aromatic Bond Count23
2D diagram of MTK

Chemical Component Summary

NameMONTELUKAST
Synonyms2-[1-[[(1R)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]ethanoic acid
Systematic Name (OpenEye OEToolkits)2-[1-[[(1R)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]ethanoic acid
FormulaC35 H36 Cl N O3 S
Molecular Weight586.183
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.352CC(C)(O)c1ccccc1CC[CH](SCC2(CC2)CC(O)=O)c3cccc(C=Cc4ccc5ccc(Cl)cc5n4)c3
SMILESOpenEye OEToolkits1.7.0CC(C)(c1ccccc1CCC(c2cccc(c2)C=Cc3ccc4ccc(cc4n3)Cl)SCC5(CC5)CC(=O)O)O
Canonical SMILESCACTVS3.352 CC(C)(O)c1ccccc1CC[C@@H](SCC2(CC2)CC(O)=O)c3cccc(/C=C/c4ccc5ccc(Cl)cc5n4)c3
Canonical SMILESOpenEye OEToolkits1.7.0 CC(C)(c1ccccc1CC[C@H](c2cccc(c2)/C=C/c3ccc4ccc(cc4n3)Cl)SCC5(CC5)CC(=O)O)O
InChIInChI1.03 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
InChIKeyInChI1.03 UCHDWCPVSPXUMX-TZIWLTJVSA-N

Drug Info: DrugBank

DrugBank IDDB00471 
NameMontelukast
Groups approved
DescriptionMontelukast was first approved for clinical use by the US FDA in 1998 as Merck's brand name Singulair.[L6301] The medication is a member of the leukotriene receptor antagonist (LTRA) category of drugs.[L6301,L6304,L6307,L6310,L6325,L6328,L6331] Although capable of demonstrating effectiveness, the use of such LTRAs like montelukast is typically in addition to or complementary with the use of inhaled corticosteroids or other agents in asthma step therapy.[A178645] Regardless, in 2008-2009, there were FDA-led investigations into the possibility of montelukast to elicit neuropsychiatric effects like agitation, hallucinations, suicidal behaviour, and others in individuals who used the medication.[A178651] And although these kinds of effects are currently included in the official prescribing information for montelukast,[L6301,L6304,L6307,L6310,L6325,L6328,L6331] the drug still sees extensive use worldwide via millions of prescriptions annually and has since become available as a generic and as a brand name product.
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
  • Montelukastum
  • Montelukast sodium
  • Montélukast
  • Montelukast
Brand Names
  • Jamp Montelukast Chewable Tablets
  • Mint-montelukast
  • Montelukast sodium
  • Bio-montelukast
  • Auro-montelukast Chewable Tablet
IndicationMontelukast is indicated for: (a) the prophylaxis and chronic treatment of asthma in adults and pediatric patients who are 12 months of age and older[L6301], although other regional health authorities specifically note this indication for adults and adolescents who are 15 years and older[L6304,L6307] and also include indications for preventing day and night-time symptoms, and the treatment of acetylsalicylic acid-sensitive asthma[L6304]; (b) the prevention of exercise-induced bronchoconstriction (EIB) in patients who are 6 years of age and older[L6301], although other regional health authorities specifically note this indication for adults and adolescents who are 15 years and older[L6304,L6307]; and (c) the relief of symptoms of seasonal allergic rhinitis in patients 2 years of age and older and perennial allergic rhinitis in patients 6 months of age and older[L6301], although other regional health authorities specifically note the relief of seasonal allergic rhinitis symptoms for adults and adolescents who are 15 years and older[L6304,L6307]. Furthermore, some formulations like chewable montelukast tablets may also be specifically indicated by particular regulatory bodies for the prophylaxis and chronic treatment of asthma, including the prevention of day and night-time symptoms, the treatment of acetylsalicylic acid based asthma, and the prevention of exercise-induced bronchoconstriction in adult and pediatric patients aged 2 and older[L6328], between the ages 2 and 5[L6325], or between the ages of 6 and 14 years.[L6331] Moreover, when employed for such indications montelukast is considered effective as monotherapy or when combined with other medications indicated for the maintenance treatment of chronic asthma.[L6304,L6328] For instance, montelukast and inhaled corticosteroids can be used concomitantly to demonstrate additive effects to control asthma or to decrease the necessary inhaled corticosteroid dose while still maintaining clinical stability.[L6304,L6328] Additionally, in patients who continue to experience asthma symptoms, montelukast can also be combined with an 'as required' short-acting beta-agonist, an inhaled corticosteroid, or inhaled corticosteroid paired with a long-acting beta-agonist.[L6304,L6328]
Categories
  • Acids, Acyclic
  • Agents Causing Muscle Toxicity
  • Agents to Treat Airway Disease
  • Anions
  • Anti-Asthmatic Agents
ATC-Code
  • R03DC03
  • R03DC53
CAS number158966-92-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Cysteinyl leukotriene receptor 1MDETGNLTVSSATCHDTIDDFRNQVYSTLYSMISVVGFFGNGFVLYVLIK...unknownantagonist
Arachidonate 5-lipoxygenaseMPSYTVTVATGSQWFAGTDDYIYLSLVGSAGCSEKHLLDKPFYNDFERGA...unknownother/unknown
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknownsubstrate
Cytochrome P450 2A6MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL787
PubChem 5281040
ChEMBL CHEMBL787
ChEBI CHEBI:50730, CHEBI:94710
CCDC/CSD UHUQUK
COD 7200840