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Details

Stereochemistry ACHIRAL
Molecular Formula C21H17FN2O2
Molecular Weight 348.3703
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIMAPIPRANT

SMILES

CC1=C(CC2=NC3=C(C=CC=C3)C=C2)C4=C(C=CC(F)=C4)N1CC(O)=O

InChI

InChIKey=FATGTHLOZSXOBC-UHFFFAOYSA-N
InChI=1S/C21H17FN2O2/c1-13-17(11-16-8-6-14-4-2-3-5-19(14)23-16)18-10-15(22)7-9-20(18)24(13)12-21(25)26/h2-10H,11-12H2,1H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula C21H17FN2O2
Molecular Weight 348.3703
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

OC-459 is a highly potent and selective CRTH2 antagonist which is active on both the recombinant and native human receptor. The Atopix lead compound OC-459 is effective in improving lung function and symptoms in patients with atopic eosinophilic asthma. This group represents 40-50% of all asthmatics and the magnitude of improvement in the responder population is equivalent to high dose inhaled corticosteroids. OC-459 has also been shown to reduce both nasal and eye symptoms in allergic subjects exposed to grass pollen. Of particular interest is the ability of OC-459 to reduce the rate of respiratory infections, an effect related to reduction in Th2 immunity which has a damaging effect on host defence. OC-459 has also demonstrated an excellent safety profile in around 800 subjects exposed drug and no safety issues have been highlighted in long term toxicology. OC-459 is in Phase 2 clinical trial in patients with moderate to severe atopic dermatitis.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
200 mg 2 times / day multiple, oral
OC-459 plasma
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
25 mg once daily, 200 mg once daily or 100 mg twice daily
Route of Administration: Oral
In Vitro Use Guide
OC-459 inhibited chemotaxis (IC₅₀ = 0.028 uM) of human Th2 lymphocytes and cytokine production (IC₅₀ = 0.019 uM) by human Th2 lymphocytes.
Substance Class Chemical
Record UNII
04XB9TB8OL
Record Status Validated (UNII)
Record Version