TARIQUIDAR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C38H38N4O6
Molecular Weight	646.7315
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(CN(CCC3=CC=C(NC(=O)C4=C(NC(=O)C5=CN=C6C=CC=CC6=C5)C=C(OC)C(OC)=C4)C=C3)CC2)C=C1OC

InChI

InChIKey=LGGHDPFKSSRQNS-UHFFFAOYSA-N

InChI=1S/C38H38N4O6/c1-45-33-18-25-14-16-42(23-28(25)19-34(33)46-2)15-13-24-9-11-29(12-10-24)40-38(44)30-20-35(47-3)36(48-4)21-32(30)41-37(43)27-17-26-7-5-6-8-31(26)39-22-27/h5-12,17-22H,13-16,23H2,1-4H3,(H,40,44)(H,41,43)

HIDE SMILES / InChI

Molecular Formula	C38H38N4O6
Molecular Weight	646.7315
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10510451
Curator's Comment: Description was created using several sources including: http://www.prnewswire.com/news-releases/xenova-group-plc-phase-iii-trials-begin-for-tariquidar-78001497.html; https://www.ncbi.nlm.nih.gov/pubmed/21600273; http://www.prnewswire.com/news-releases/xenovas-tariquidar-granted-fda-fast-track-status-76050817.html

Tariquidar, a non-competitive, specific P-glycoprotein (Pgp) inhibitor, is an anthranilamide derivative with multidrug resistance properties. Tariquidar binds to the ATP-binding cassette (ABC) transport protein Pgp, thereby inhibiting transmembrane transport of anticancer drugs resulting in their increased intracellular concentrations augmenting cytotoxicity of an anticancer drug. Tariquidar was discovered by Xenova Group and was developed for the treatment of multidrug resistance in cancer. In October 2002 the US Food and Drug Administration (FDA) has granted fast track review status to tariquidar for the treatment of multi-drug resistance in first-line treatment of non-small cell lung cancer (NSCLC) patients. Tariquidar is still undergoing research as an adjuvant against multidrug resistance in cancer.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
P-glycoprotein 1 54 Target ID: CHEMBL3467 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10510451	Inhibitor 8297		5.1 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Non-small cell lung cancer 206 Sources: https://clinicaltrials.gov/ct2/show/NCT00042315	Primary		Phase III 656	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY100719	https://www.001chemical.com/chem/search?q=DY100719
1PlusChem LLC	1P002J6T	https://www.1pchem.com/search?query=1P002J6T
1PlusChem LLC	1P00ECVH	https://www.1pchem.com/search?query=1P00ECVH
A2B Chem	AB17381	http://a2bchem.com/prod/AB17381
AA Blocks	AA002IND	http://aablocks.com/goods/Goods/detail?id=AA002IND
AK Scientific	Y0469	https://aksci.com/item_detail.php?cat=Y0469
AOBIOUS INC	AOB87165	http://aobious.com/aobious/search?search_query=AOB87165
Ambeed	A251517	http://www.ambeed.com/search/Search.html?keyword=A251517
ApexBio Technology	A8208	https://www.apexbt.com/catalogsearch/result/?q=A8208
AstaTech	82846	http://astatechinc.com/CPSResult.php?CRNO=82846
Axon MedChem	1960	https://www.axonmedchem.com/product/1960
BLD Pharm	BD630796	http://www.bldpharm.com/search/Search.html?keyword=BD630796
BOC Sciences	206873-63-4	http://www.bocsci.com/description.asp?cas=206873-63-4
Chem Scene	CS-0722	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0722
Chem Scene	CS-1260	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1260
ChemShuttle	109824	https://www.chemshuttle.com/catalogsearch/result/?q=109824
Combi-Blocks	QK-7548	http://www.combi-blocks.com/cgi-bin/find.cgi?QK-7548
Debye Scientific	DA-08376	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-08376
Excenen	EX-A231	http://www.excenen.com/searchresultlist.php?id=EX-A231
Hairui	HR117480	http://www.hairuichem.com/en/product/search.do?q=HR117480
KeyOrganics	AS-75190	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75190
Lab Seeker	SC-50718	http://www.labseeker.com/search.php?keywords=SC-50718&category=0
LabSeeker	SC-50718	http://www.labseeker.com/search.php?keywords=SC-50718&category=0
Matrix Scientific	98181	http://www.matrixscientific.com/098181.html
MedChem Express	HY-10550	https://www.medchemexpress.com/search.html?q=HY-10550A&ft=&fa=&fp=
MedChem Express	HY-10550A	https://www.medchemexpress.com/search.html?q=HY-10550A&ft=&fa=&fp=
MolPort	MolPort-027-835-494	https://www.molport.com/shop/molecule-link/MolPort-027-835-494
MolPort	MolPort-042-624-565	https://www.molport.com/shop/molecule-link/MolPort-042-624-565
MolPort	MolPort-046-416-861	https://www.molport.com/shop/molecule-link/MolPort-046-416-861
Molcore	MC100719	http://www.molcore.com/CatMC100719.html
Molnova	M13215	https://www.molnova.com/en/serch-list.html?keywords=M13215
Molnova	M15368	https://www.molnova.com/en/serch-list.html?keywords=M15368
MuseChem	I002592	https://www.musechem.com/product/I002592.html
PI Chemicals	PI-37144	http://www.pipharm.com/catalog_products/PI-37144.html
Selleck Chemicals	S8028	http://www.selleckchem.com/search.html?searchDTO.searchParam=S8028
ShangHai Biochempartner	BCP000665	http://www.biochempartner.com/search_BCP000665
ShangHai Biochempartner	BCP06102	http://www.biochempartner.com/search_BCP06102
ShangHai Biochempartner	BCP18814	http://www.biochempartner.com/search_BCP18814
Synthonix	15195	https://synthonix.com/catalogsearch/result/?q=15195
TargetMol	T6287	https://www.targetmol.com/search?keyword=T6287
Tetrahedron	TS90410	http://www.thsci.com/search.do?q=TS90410
Toronto Research Chemicals	B207535	https://www.trc-canada.com/product-detail/?CatNum=B207535
Toronto Research Chemicals	T007600	https://www.trc-canada.com/product-detail/?CatNum=T007600
Vesino Industrial Co Ltd	VA11819	http://www.vsnchem.com/search.do?a=s&psize=20&q=VA11819
eMolecules	44689692	https://orderbb.emolecules.com/search/#?query=44689692
eMolecules	50282717	https://orderbb.emolecules.com/search/#?query=50282717
mcule	MCULE-9666844484	https://mcule.com/MCULE-9666844484/

PubMed

Title	Date	PubMed
Modulation of drug resistance transporters as a strategy for treating myelodysplastic syndrome.	2004 Dec	15494300
Increasing oxime efficacy by blood-brain barrier modulation.	2011 Sep 25	21600273

Patents

Sample Use Guides

In Vivo Use Guide

40 mg/m2 docetaxel over 1 hour on days 1 and 8 and 150 mg/m2 tariquidar over 30 minutes on days 8 and 22.

Route of Administration: Intravenous

In Vitro Use Guide

The effect of increasing concentrations of XR9576 (tariquidar) on the steady-state accumulation of [3H]-vinblastine (100 nm) and [3H]-paclitaxel (1 um) was measured in CHrB30 cells at 37°C. XR9576 (tariquidar) was shown to be a potent modulator of Pgp mediated [3H]-vinblastine and [3H]-paclitaxel transport as it increased the steady-state accumulation of these cytotoxics in the P-gp over-expressing CHrB30 cells with EC50 = 487+/-50 nM compared to non-Pgp-expressing AuxB1 cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:39:10 GMT 2023` Edited by `admin` on `Fri Dec 15 15:39:10 GMT 2023`
Record UNII	J58862DTVD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TARIQUIDAR

Official Name

English

XR9576

Code

English

XR-9576

Code

English

TARIQUIDAR [USAN]

Common Name

English

3-QUINOLINECARBOXAMIDE,N-(2-(((4-(2-(3,4-DIHYDRO-6,7-DIMETHOXY-2(1H)-ISOQUINOLINYL)ETHYL)PHENYL)AMINO)CARBONYL)-4,5-DIMETHOXYPHENYL)-

Common Name

English

N-[2-[[4-[2-(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]phenyl]carbamoyl]-4,5-dimethoxyphenyl]quinoline-3-carboxamide

Systematic Name

English

TARIQUIDAR [MI]

Common Name

English

Tariquidar [WHO-DD]

Common Name

English

tariquidar [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1744