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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

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
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 Feb
Update on the status of DP2 receptor antagonists; from proof of concept through clinical failures to promising new drugs.
2014 Jan
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
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
timapiprant [INN]
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 Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL560993
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
SMS_ID
300000008740
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
NCI_THESAURUS
C152633
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
DRUG BANK
DB11900
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
CAS
851723-84-7
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
FDA UNII
04XB9TB8OL
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID00234343
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
INN
10483
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
PUBCHEM
11462174
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
PRIMARY
CAS
1422181-22-3
Created by admin on Sat Dec 16 04:36:09 GMT 2023 , Edited by admin on Sat Dec 16 04:36:09 GMT 2023
NO STRUCTURE GIVEN