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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

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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.