TOMELUKAST SODIUM

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 Search

SMILES

[Na+].CCCC1=C(OCCCCC2=NN=N[N-]2)C=CC(C(C)=O)=C1O

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

Molecular Formula	C16H21N4O3
Molecular Weight	317.3629
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18031150 | https://www.ncbi.nlm.nih.gov/pubmed/3981452

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cysteinyl leukotriene receptor 1 18 Target ID: Q9Y271 Gene ID: 10800.0 Gene Symbol: CYSLTR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3981452	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2554766	Primary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Mechanism of phosgene-induced lung toxicity: role of arachidonate mediators.	1990 Nov	2125593
Endogenously formed leukotriene C4 activates LTC4 receptors in guinea pig tracheal strips.	1991 Mar 26	1651863
Anti-leukotriene effects of WY-50,295 tromethamine in isolated guinea pig pulmonary tissues.	1993 Apr 6	8482329
In vivo characterization of zymosan-induced mouse peritoneal inflammation.	1994 Jun	8014878
Peroxisome proliferator-activated receptor alpha required for gene induction by dehydroepiandrosterone-3 beta-sulfate.	1996 Jul	8700121
Pharmacology of leukotriene receptor antagonists.	1998 Jun	9620942
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	12115725
Induction of apoptosis in human and rat glioma by agonists of the nuclear receptor PPARgamma.	2002 Jun	12065618
Leukotrienes mediate murine bronchopulmonary hyperreactivity, inflammation, and part of mucosal metaplasia and tissue injury induced by recombinant murine interleukin-13.	2003 Apr	12654629
Actions of cysteinyl leukotrienes in the enteric nervous system of guinea-pig stomach and small intestine.	2003 Jan 10	12505531
Inverse agonist activity of selected ligands of the cysteinyl-leukotriene receptor 1.	2004 Apr	14718577
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.	2004 Oct	15491415
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	19398503

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 17:51:02 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:02 GMT 2025`
Record UNII	G4YL9T9SOU
Record Status	`Validated (UNII)`
Record Version

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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)

Preferred Name

English

Code System Code Type Description

PUBCHEM

162623868

Created by admin on Mon Mar 31 17:51:02 GMT 2025 , Edited by admin on Mon Mar 31 17:51:02 GMT 2025

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FDA UNII

G4YL9T9SOU

Created by admin on Mon Mar 31 17:51:02 GMT 2025 , Edited by admin on Mon Mar 31 17:51:02 GMT 2025

PRIMARY

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TOMELUKAST

PARENT -> SALT/SOLVATE

Amount: