TR-14035

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H21Cl2NO5
Molecular Weight	474.333
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=CC(OC)=C1C2=CC=C(C[C@H](NC(=O)C3=C(Cl)C=CC=C3Cl)C(O)=O)C=C2

InChI

InChIKey=DRSJLVGDSNWQBI-SFHVURJKSA-N

InChI=1S/C24H21Cl2NO5/c1-31-19-7-4-8-20(32-2)21(19)15-11-9-14(10-12-15)13-18(24(29)30)27-23(28)22-16(25)5-3-6-17(22)26/h3-12,18H,13H2,1-2H3,(H,27,28)(H,29,30)/t18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C24H21Cl2NO5
Molecular Weight	474.333
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://adisinsight.springer.com/drugs/800012563
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11937364

TR14035 (SB 683698) is a dual integrin alpha-4/beta-1 and alpha-4/beta-7 antagonist. Integrin alpha-4/beta-1 and alpha-4/beta-7 are key regulators of physiologic and pathologic responses in inflammation and autoimmune disease. It was originated by Tanabe Seiyaku and was being developed by Tanabe Research Laboratories and GlaxoSmithKline in Japan, the USA and Europe. TR 4035 was being developed in phase II clinical studies for the treatment of asthma and rheumatoid arthritis. It may also have had potential in a number of other inflammatory diseases, including inflammatory bowel disease and multiple sclerosis, for which it was at the phase I stage of clinical investigation. However, development has now been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Integrin alpha-4/beta-1 6 Target ID: CHEMBL1907599 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11937364	Antagonist 2849		87.0 nM [IC50]
Integrin alpha-4/beta-7 1 Target ID: CHEMBL2095184 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11937364	Antagonist 2849		7.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: http://adisinsight.springer.com/drugs/800012563	Primary	Phase II 1147	Unknown Approved Use Unknown
Irritable bowel syndrome 61 Sources: http://adisinsight.springer.com/drugs/800012563	Primary	Phase II 1147	Unknown Approved Use Unknown
Multiple sclerosis 107 Sources: http://adisinsight.springer.com/drugs/800012563	Primary	Phase I 438	Unknown Approved Use Unknown
Rheumatoid arthritis 320 Sources: http://adisinsight.springer.com/drugs/800012563	Primary	Phase II 1147	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Characterization of hepatobiliary transport systems of a novel alpha4beta1/alpha4beta7 dual antagonist, TR-14035.	2006-11	16969695
A small molecule, orally active, alpha4beta1/alpha4beta7 dual antagonist reduces leukocyte infiltration and airway hyper-responsiveness in an experimental model of allergic asthma in Brown Norway rats.	2006-03	16432509
Pharmacokinetics and metabolism of TR-14035, a novel antagonist of a4ss1/a4ss7 integrin mediated cell adhesion, in rat and dog.	2005-04	16019958
Role of human liver cytochrome P450 2C9 in the metabolism of a novel alpha4beta1/alpha4beta7 dual antagonist, TR-14035.	2005-04	15855725
Alpha(4)beta(7)/alpha(4)beta(1) dual integrin antagonists block alpha(4)beta(7)-dependent adhesion under shear flow.	2002-07	12065712
Synthesis and SAR of N-benzoyl-L-biphenylalanine derivatives: discovery of TR-14035, a dual alpha(4)beta(7)/alpha(4)beta(1) integrin antagonist.	2002-06	11937364

Patents

Sample Use Guides

In Vivo Use Guide

TR14035 was being developed in phase II clinical studies for the treatment of asthma and rheumatoid arthritis however dosafe is not known. Oral TR14035 3-30 mg/kg was active in several preclinical in vivo studies.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:44:53 GMT 2025` Edited by `admin` on `Mon Mar 31 23:44:53 GMT 2025`
Record UNII	UW585PBD7S
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SB-683698

Preferred Name

English

TR-14035

Code

English

(2S)-2-((2,6-DICHLOROBENZOYL)AMINO)-3-(4-(2,6-DIMETHOXYPHENYL)PHENYL)PROPANOIC ACID

Systematic Name

English

TR14035

Code

English

(1,1'-BIPHENYL)-4-PROPANOIC ACID, .ALPHA.-((2,6-DICHLOROBENZOYL)AMINO)-2',6'-DIMETHOXY-, (.ALPHA.S)-

Systematic Name

English

Code System Code Type Description

CAS

232271-19-1

Created by admin on Mon Mar 31 23:44:53 GMT 2025 , Edited by admin on Mon Mar 31 23:44:53 GMT 2025

PRIMARY

FDA UNII

UW585PBD7S

Created by admin on Mon Mar 31 23:44:53 GMT 2025 , Edited by admin on Mon Mar 31 23:44:53 GMT 2025

PRIMARY

PUBCHEM

9912743

Created by admin on Mon Mar 31 23:44:53 GMT 2025 , Edited by admin on Mon Mar 31 23:44:53 GMT 2025

PRIMARY

EPA CompTox

DTXSID001026007

Created by admin on Mon Mar 31 23:44:53 GMT 2025 , Edited by admin on Mon Mar 31 23:44:53 GMT 2025

PRIMARY

Related Record Type Details


					UW585PBD7S

TR-14035

ACTIVE MOIETY

Comments:

SB-683698 (VLA4 integrin antagonist)


					UW585PBD7S

TR-14035

ACTIVE MOIETY

Comments:

Class: Anti-inflammatory; Antiasthmatic; Antihyperglycaemic; Antirheumatic; Irritable bowel syndrome therapy

Details

SMILES

InChI

DescriptionSources: http://adisinsight.springer.com/drugs/800012563Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11937364

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: http://adisinsight.springer.com/drugs/800012563
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11937364