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Details

Stereochemistry ACHIRAL
Molecular Formula C16H22N4O3
Molecular Weight 318.3709
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOMELUKAST

SMILES

CCCC1=C(O)C(=CC=C1OCCCCC2=NN=NN2)C(C)=O

InChI

InChIKey=MWYHLEQJTQJHSS-UHFFFAOYSA-N
InChI=1S/C16H22N4O3/c1-3-6-13-14(9-8-12(11(2)21)16(13)22)23-10-5-4-7-15-17-19-20-18-15/h8-9,22H,3-7,10H2,1-2H3,(H,17,18,19,20)

HIDE SMILES / InChI

Molecular Formula C16H22N4O3
Molecular Weight 318.3709
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tomelukast (previously known as LY171883), an orally active antagonist of the CysLT1 receptor (leukotriene D4), which was investigated to treat asthma, but this study was discontinued because of adverse gastrointestinal effect.

Originator

Curator's Comment: # Eli Lilly

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9Y271
Gene ID: 10800.0
Gene Symbol: CYSLTR1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Endogenously formed leukotriene C4 activates LTC4 receptors in guinea pig tracheal strips.
1991 Mar 26
Anti-leukotriene effects of WY-50,295 tromethamine in isolated guinea pig pulmonary tissues.
1993 Apr 6
In vivo characterization of zymosan-induced mouse peritoneal inflammation.
1994 Jun
Peroxisome proliferator-activated receptor alpha required for gene induction by dehydroepiandrosterone-3 beta-sulfate.
1996 Jul
Induction of apoptosis in human and rat glioma by agonists of the nuclear receptor PPARgamma.
2002 Jun
Leukotrienes mediate murine bronchopulmonary hyperreactivity, inflammation, and part of mucosal metaplasia and tissue injury induced by recombinant murine interleukin-13.
2003 Apr
Inverse agonist activity of selected ligands of the cysteinyl-leukotriene receptor 1.
2004 Apr
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
Molecular basis for reduced estrone sulfate transport and altered modulator sensitivity of transmembrane helix (TM) 6 and TM17 mutants of multidrug resistance protein 1 (ABCC1).
2009 Jul
Patents

Sample Use Guides

600 mg twice daily for 6 weeks
Route of Administration: Oral
In Vitro Use Guide
LY171883 functioned primarily as a leukotriene receptor antagonist with minimal pharmacological activity attributable to its ability to potentiate isoprenaline. Relaxation of carbachol-contracted guinea-pig trachea by isoprenaline was enhanced by the three agents in a dose-dependent manner. A two-fold enhancement of isoprenaline-induced smooth muscle relaxation was produced by 2.5 microM IBMX, 28 microM LY171883, or 140 microM theophylline. LY171883 totally inhibited the response and had significant LTE4 receptor antagonist activity even at 10-fold lower concentrations.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:18 UTC 2023
Edited
by admin
on Fri Dec 15 15:16:18 UTC 2023
Record UNII
59762X5CLS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOMELUKAST
INN   MART.   USAN  
INN   USAN  
Official Name English
ETHANONE, 1-(2-HYDROXY-3-PROPYL-4-(4-(1H-TETRAZOL-5-YL)BUTOXY)PHENYL)-
Systematic Name English
TOMELUKAST [MART.]
Common Name English
LY-171883
Code English
LY-171833
Code English
LY171883
Code English
tomelukast [INN]
Common Name English
TOMELUKAST [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29712
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID7020344
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
CHEBI
75310
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
FDA UNII
59762X5CLS
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
CAS
88107-10-2
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
INN
6289
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
PUBCHEM
3969
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL162358
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
NCI_THESAURUS
C74135
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
USAN
W-40
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
SMS_ID
100000077788
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
EVMPD
SUB11184MIG
Created by admin on Fri Dec 15 15:16:18 UTC 2023 , Edited by admin on Fri Dec 15 15:16:18 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY