TIMAPIPRANT

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 Search

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

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

Description
Sources: http://www.atopixtherapeutics.com/research-and-development/OC459.html | https://www.ncbi.nlm.nih.gov/pubmed/24073896
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
G protein-coupled receptor 44 7 Target ID: CHEMBL5071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24073896 \| https://www.ncbi.nlm.nih.gov/pubmed/22106101	Antagonist 2778		4.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://clinicaltrials.gov/ct2/show/NCT02660489 http://adisinsight.springer.com/drugs/800030678	Primary		Phase III 656	Unknown Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
15 h REVIEW https://pubmed.ncbi.nlm.nih.gov/23025511/	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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 inducer 781	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19608418/	no [IC50 >30 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19608418/	no [IC50 >30 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19608418/	no [IC50 >30 uM]
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19608418/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363680186	no

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY114834	https://www.001chemical.com/chem/search?q=DY114834
1PlusChem LLC	1P004NDN	https://www.1pchem.com/search?query=1P004NDN
A2B Chem	AC16123	http://a2bchem.com/prod/AC16123
AChemBlock	L22431	http://www.achemblock.com/catalogsearch/result/?q=L22431
AK Scientific	Y0372	https://aksci.com/item_detail.php?cat=Y0372
AOBIOUS INC	AOB87167	http://aobious.com/aobious/search?search_query=AOB87167
Angene	AGN-PC-0WH8JH	http://www.angenechemical.com/productshow/AGN-PC-0WH8JH.html
ApexBio Technology	B1535	https://www.apexbt.com/catalogsearch/result/?q=B1535
AstaTech	43014	http://astatechinc.com/CPSResult.php?CRNO=43014
Axon MedChem	1913	https://www.axonmedchem.com/product/1913
BOC Sciences	851723-84-7	http://www.bocsci.com/description.asp?cas=851723-84-7
Cayman Chemical	12027	http://www.caymanchem.com/app/template/Product.vm/catalog/12027
Chem Scene	CS-1285	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1285
ChemShuttle	104927	https://www.chemshuttle.com/catalogsearch/result/?q=104927
Debye Scientific	DA-18057	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-18057
Excenen	EX-A090	http://www.excenen.com/searchresultlist.php?id=EX-A090
Hairui	TIJL008	http://www.hairuichem.com/en/product/search.do?q=TIJL008
KeyOrganics	AS-56024	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56024
Lab Network	LN00198814	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00198814
Lab Seeker	SC-93534	http://www.labseeker.com/search.php?keywords=SC-93534&category=0
LabSeeker	SC-93534	http://www.labseeker.com/search.php?keywords=SC-93534&category=0
Matrix Scientific	96906	http://www.matrixscientific.com/096906.html
MedChem Express	HY-15342	https://www.medchemexpress.com/search.html?q=HY-15342&ft=&fa=&fp=
MolPort	MolPort-047-156-065	https://www.molport.com/shop/molecule-link/MolPort-047-156-065
Molcore	MC114834	http://www.molcore.com/CatMC114834.html
Molnova	M17616	https://www.molnova.com/en/serch-list.html?keywords=M17616
MuseChem	I005109	https://www.musechem.com/product/I005109.html
PI Chemicals	PI-37381	http://www.pipharm.com/catalog_products/PI-37381.html
Ryan Scientific	MK-8245	https://ryansci.com/products?q=MK-8245&list_q=&search_type=exact
ShangHai Biochempartner	BCP000546	http://www.biochempartner.com/search_BCP000546
ShangHai Biochempartner	BCP04237	http://www.biochempartner.com/search_BCP04237
TargetMol	T2664	https://www.targetmol.com/search?keyword=T2664
Toronto Research Chemicals	O135000	https://www.trc-canada.com/product-detail/?CatNum=O135000
eMolecules	44470836	https://orderbb.emolecules.com/search/#?query=44470836
eNovation Chemicals	D572832	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D572832&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-6287276672	https://mcule.com/MCULE-6287276672/

PubMed

Title	Date	PubMed
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	22106101
Update on the status of DP2 receptor antagonists; from proof of concept through clinical failures to promising new drugs.	2014 Jan	24073896

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 Created by `admin` on `Sat Dec 16 04:36:09 UTC 2023` Edited by `admin` on `Sat Dec 16 04:36:09 UTC 2023`
Record UNII	04XB9TB8OL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIMAPIPRANT

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