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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=CC=C3C=CC=CC3=N2)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

Description
Curator's Comment: http://www.atopixtherapeutics.com/press-releases/Atopix%20-%20OC459%20Ph2%20Atopic%20Dermatitis%20Study%20Final%20-%2017Feb16.pdf https://www.ncbi.nlm.nih.gov/pubmed/22106101

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15 h
200 mg 2 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
OC-459 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Update on the status of DP2 receptor antagonists; from proof of concept through clinical failures to promising new drugs.
2014-01
Pharmacologic profile of OC000459, a potent, selective, and orally active D prostanoid receptor 2 antagonist that inhibits mast cell-dependent activation of T helper 2 lymphocytes and eosinophils.
2012-02
Patents

Patents

Sample Use Guides

25 mg once daily, 200 mg once daily or 100 mg twice daily
Route of Administration: Oral
OC-459 inhibited chemotaxis (IC₅₀ = 0.028 uM) of human Th2 lymphocytes and cytokine production (IC₅₀ = 0.019 uM) by human Th2 lymphocytes.
Name Type Language
TIMAPIPRANT
INN  
INN  
Official Name English
timapiprant [INN]
Preferred Name English
OC-000459
Code English
CHF-6532
Code English
OC000459
Code English
OC459
Code English
1H-INDOLE-1-ACETIC ACID, 5-FLUORO-2-METHYL-3-(2-QUINOLINYLMETHYL)-
Systematic Name English
OC-459
Common Name English
ODC-9101
Common Name English
Timapiprant [WHO-DD]
Common Name English
(5-FLUORO-2-METHYL-3-QUINOLIN-2-YLMETHYLINDO-1-YL)-ACETIC ACID
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C574
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL560993
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
SMS_ID
300000008740
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
NCI_THESAURUS
C152633
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
DRUG BANK
DB11900
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
CAS
851723-84-7
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
FDA UNII
04XB9TB8OL
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID00234343
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
INN
10483
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
PUBCHEM
11462174
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
PRIMARY
CAS
1422181-22-3
Created by admin on Mon Mar 31 21:22:32 GMT 2025 , Edited by admin on Mon Mar 31 21:22:32 GMT 2025
NO STRUCTURE GIVEN