TIPLASININ

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H16F3NO4
Molecular Weight	439.3833
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C(=O)C1=CN(CC2=CC=CC=C2)C3=CC=C(C=C13)C4=CC=C(OC(F)(F)F)C=C4

InChI

InChIKey=ODXQFEWQSHNQNI-UHFFFAOYSA-N

InChI=1S/C24H16F3NO4/c25-24(26,27)32-18-9-6-16(7-10-18)17-8-11-21-19(12-17)20(22(29)23(30)31)14-28(21)13-15-4-2-1-3-5-15/h1-12,14H,13H2,(H,30,31)

HIDE SMILES / InChI

Molecular Formula	C24H16F3NO4
Molecular Weight	439.3833
Charge	0
Count

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

Description
Sources: http://adisinsight.springer.com/drugs/800021321
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15214776 https://www.ncbi.nlm.nih.gov/pubmed/18392333 https://www.ncbi.nlm.nih.gov/pubmed/17276980

Tiplasinin (PAI-039) is an orally efficacious and selective plasminogen activator inhibitor-1 (PAI-1) inhibitor. Tiplasinin bound specifically to the active conformation of PAI-1 and exhibited reversible inactivation of PAI-1 in vitro. Tiplaxtinin exhibited in vivo oral efficacy in two different models of acute arterial thrombosis. The remarkable preclinical safety and metabolic stability profiles of tiplaxtinin led to advancing the compound to Phase-I clinical trial for Thrombosis, which was later discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Plasminogen activator inhibitor-1 2 Target ID: CHEMBL3475 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17276980 \| https://www.ncbi.nlm.nih.gov/pubmed/15214776 \| https://www.ncbi.nlm.nih.gov/pubmed/18177924	Inhibitor 8297		2.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thrombosis 22 Sources: http://adisinsight.springer.com/drugs/800021321	Primary		Phase I 428	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00397K	https://www.1pchem.com/search?query=1P00397K
AChemBlock	O33835	http://www.achemblock.com/catalogsearch/result/?q=O33835
AOBIOUS INC	AOB2258	http://aobious.com/aobious/search?search_query=AOB2258
Alfa Chemistry	ACM393105538	http://www.alfa-chemistry.com/search.aspx?q=ACM393105538
Angene	AGN-PC-0WHAOL	http://www.angenechemical.com/productshow/AGN-PC-0WHAOL.html
ApexBio Technology	B5906	https://www.apexbt.com/catalogsearch/result/?q=B5906
AstaTech	44102	http://astatechinc.com/CPSResult.php?CRNO=44102
Axon MedChem	1383	https://www.axonmedchem.com/product/1383
BLD Pharm	BD448330	http://www.bldpharm.com/search/Search.html?keyword=BD448330
BOC Sciences	393105-53-8	http://www.bocsci.com/description.asp?cas=393105-53-8
Chem Scene	CS-3928	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3928
ChemShuttle	152122	https://www.chemshuttle.com/catalogsearch/result/?q=152122
Combi-Blocks	QJ-0146	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-0146
Excenen	EX-A114	http://www.excenen.com/searchresultlist.php?id=EX-A114
KeyOrganics	AS-73537	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-73537
MedChem Express	HY-15253	https://www.medchemexpress.com/search.html?q=HY-15253&ft=&fa=&fp=
MolPort	MolPort-021-805-012	https://www.molport.com/shop/molecule-link/MolPort-021-805-012
Molnova	M14351	https://www.molnova.com/en/serch-list.html?keywords=M14351
MuseChem	I003439	https://www.musechem.com/product/I003439.html
Selleck Chemicals	S7922	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7922
ShangHai Biochempartner	BCP02216	http://www.biochempartner.com/search_BCP02216
Synovel	SN-0320	http://www.synovellab.com/?s=SN-0320&submit=Search
TargetMol	T2030	https://www.targetmol.com/search?keyword=T2030
Tocris	5565	https://www.tocris.com/search.php?Type=QuickSearch&Value=5565
Toronto Research Chemicals	C991925	https://www.trc-canada.com/product-detail/?CatNum=C991925
Toronto Research Chemicals	T444895	https://www.trc-canada.com/product-detail/?CatNum=T444895
Vesino Industrial Co Ltd	VA11996	http://www.vsnchem.com/search.do?a=s&psize=20&q=VA11996
eMolecules	36367051	https://orderbb.emolecules.com/search/#?query=36367051
eNovation Chemicals	D320026	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D320026&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-7392828010	https://mcule.com/MCULE-7392828010/

PubMed

Title	Date	PubMed
		252160100

Patents

Sample Use Guides

In Vivo Use Guide

Rodents: Phase 1 animals receiving low-dose (1 mg/kg oral gavage) Tiplasinin demonstrated a 52% decrease in thrombus weight (TW) versus controls with significant reductions in active plasma PAI-1, while the high-dose (10 mg/kg oral gavage) group demonstrated a 23% reduction in TW versus controls

Route of Administration: Oral

In Vitro Use Guide

Tiplaxtinin inhibited rhPAI-1 activity measured in vitro by the fibrinolysis assay in a dose-dependent manner with IC50 22 uM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:02:20 GMT 2023` Edited by `admin` on `Fri Dec 15 16:02:20 GMT 2023`
Record UNII	L396QIB983
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIPLASININ

Official Name

English

TIPLASININ [USAN]

Common Name

English

[1-Benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl]oxoacetic acid

Systematic Name

English

tiplasinin [INN]

Common Name

English

PAI-039

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29750