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Details

Stereochemistry ACHIRAL
Molecular Formula C16H21N4O3.Na
Molecular Weight 340.3527
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOMELUKAST SODIUM

SMILES

[Na+].CCCC1=C(O)C(=CC=C1OCCCCC2=NN=N[N-]2)C(C)=O

InChI

InChIKey=WGUJPHDKJRVHMX-UHFFFAOYSA-M
InChI=1S/C16H22N4O3.Na/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;/h8-9H,3-7,10H2,1-2H3,(H2,17,18,19,20,21,22);/q;+1/p-1

HIDE SMILES / InChI
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
In vivo characterization of zymosan-induced mouse peritoneal inflammation.
1994 Jun
Enhanced activity of Ca2+-activated K+ channels by 1-[2-hydroxy-3-propyl-4-[(1H-tetrazol-5-yl)butoxyl]phenyl] ethanone (LY-171883) in neuroendocrine and neuroblastoma cell lines.
2002 Aug
Leukotrienes mediate murine bronchopulmonary hyperreactivity, inflammation, and part of mucosal metaplasia and tissue injury induced by recombinant murine interleukin-13.
2003 Apr
Actions of cysteinyl leukotrienes in the enteric nervous system of guinea-pig stomach and small intestine.
2003 Jan 10
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.
Name Type Language
TOMELUKAST SODIUM
Common Name English
ETHANONE, 1-(2-HYDROXY-3-PROPYL-4-(4-(1H-TETRAZOL-5-YL)BUTOXY)PHENYL)-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
162623868
Created by admin on Fri Dec 15 15:13:53 UTC 2023 , Edited by admin on Fri Dec 15 15:13:53 UTC 2023
PRIMARY
FDA UNII
G4YL9T9SOU
Created by admin on Fri Dec 15 15:13:53 UTC 2023 , Edited by admin on Fri Dec 15 15:13:53 UTC 2023
PRIMARY