TUROFEXORATE ISOPROPYL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H24F2N2O3
Molecular Weight	438.4665
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC(=O)C1=CN(CC(C)(C)C2=C1NC3=C2C=CC=C3)C(=O)C4=CC=C(F)C(F)=C4

InChI

InChIKey=INASOKQDNHHMRE-UHFFFAOYSA-N

InChI=1S/C25H24F2N2O3/c1-14(2)32-24(31)17-12-29(23(30)15-9-10-18(26)19(27)11-15)13-25(3,4)21-16-7-5-6-8-20(16)28-22(17)21/h5-12,14,28H,13H2,1-4H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19159286
Curator's Comment: Description was created based on several sources, including http://www.pharmacodia.com/yaodu/html/v1/chemicals/ba3c5e7b68dbdb900c4ee701df6cd6b5.html http://adisinsight.springer.com/drugs/800025892

Turofexorate Isopropyl (XL335) is a potent, selective, and orally bioavailable FXR agonist. Binds to the ligand-binding domain (LBD) of human FXR. Turofexorate Isopropyl resides in a predominately hydrophobic pocket with only a few polar atoms making contact with WAY-362450. Turofexorate Isopropyl promotes transcription of the human BSEP, human SHP, and mouse IBABP genes utilizing reporter constructs with EC50 of 17, 230, and 33 nM, respectively in promoter assays. Turofexorate Isopropyl had been in phase I clinical trials for the treatment of hyperlipidemia. This compound was originally discovered by Exelixis Pharmaceuticals, then licensed to Wyeth (now a wholly-owned subsidiary of Pfizer). However, the studies were discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bile acid receptor FXR 31 Target ID: CHEMBL2047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19159286	Agonist 2678		4.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperlipidemia 80 Sources: http://adisinsight.springer.com/drugs/800025892	Primary		Phase I 428	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00ECVN	https://www.1pchem.com/search?query=1P00ECVN
AK Scientific	X7601	https://aksci.com/item_detail.php?cat=X7601
Angene	AGN-PC-0MXHY8	http://www.angenechemical.com/productshow/AGN-PC-0MXHY8.html
ApexBio Technology	B1528	https://www.apexbt.com/catalogsearch/result/?q=B1528
AstaTech	W12857	http://astatechinc.com/CPSResult.php?CRNO=W12857
Axon MedChem	1749	https://www.axonmedchem.com/product/1749
BOC Sciences	629664-81-9	http://www.bocsci.com/description.asp?cas=629664-81-9
Chem Scene	CS-0316	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0316
ChemShuttle	132904	https://www.chemshuttle.com/catalogsearch/result/?q=132904
Combi-Blocks	QV-5717	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-5717
Debye Scientific	DB-073232	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-073232
Excenen	EX-A162	http://www.excenen.com/searchresultlist.php?id=EX-A162
KeyOrganics	AS-55045	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-55045
Lab Seeker	SC-95561	http://www.labseeker.com/search.php?keywords=SC-95561&category=0
LabSeeker	SC-95561	http://www.labseeker.com/search.php?keywords=SC-95561&category=0
Matrix Scientific	95358	http://www.matrixscientific.com/095358.html
MedChem Express	HY-50911	https://www.medchemexpress.com/search.html?q=HY-50911&ft=&fa=&fp=
MolPort	MolPort-023-293-510	https://www.molport.com/shop/molecule-link/MolPort-023-293-510
Molnova	M15379	https://www.molnova.com/en/serch-list.html?keywords=M15379
Selleck Chemicals	S2694	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2694
ShangHai Biochempartner	BCP001006	http://www.biochempartner.com/search_BCP001006
ShangHai Biochempartner	BCP08249	http://www.biochempartner.com/search_BCP08249
WuXi AppTec	WXC04770	https://www.labnetwork.com/frontend-app/p/#!/supplier/wuxi/product/WXC04770
eMolecules	37153208	https://orderbb.emolecules.com/search/#?query=37153208
eNovation Chemicals	D320038	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D320038&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-8744481111	https://mcule.com/MCULE-8744481111/

PubMed

Title	Date	PubMed
		252160417
A synthetic farnesoid X receptor (FXR) agonist promotes cholesterol lowering in models of dyslipidemia.	2009 Mar	19136377

Patents

Sample Use Guides

In Vivo Use Guide

capsule, single oral doses from 10 mg to 450 mg

Route of Administration: Oral

In Vitro Use Guide

Turofexorate Isopropyl (WAY-362450) at concentration of 1 μM significantly induces mRNAs encoding for BSEP, SHP, and IBABP in human cell cultures to 13-, 2-, and 20-fold, respectively. Turofexorate Isopropyl at concentration of 1 uM suppresses interleukin-6-induced CRP expression in human Hep3B hepatoma cells, and the inhibitory effect is attenuated when knockdown of FXR by short interfering RNA.

Name

Type

Language

TUROFEXORATE ISOPROPYL

Official Name

English

FXR-450

Code

English

Isopropyl 3-(3,4-difluorobenzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate

Systematic Name

English

XL-335

Code

English

XL335

Code

English

AZEPINO(4,5-B)INDOLE-5-CARBOXYLIC ACID, 3-(3,4-DIFLUOROBENZOYL)-1,2,3,6-TETRAHYDRO-1,1-DIMETHYL-,1-METHYLETHYL ESTER

Common Name

English

TUROFEXORATE ISOPROPYL [USAN]

Common Name

English

WAY-362450

Code

English

turofexorate isopropyl [INN]

Common Name

English

Turofexorate isopropyl [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703