Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C38H38N4O6.2CH4O3S |
| Molecular Weight | 838.943 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CS(O)(=O)=O.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=FBCFBFPCZHHRMA-UHFFFAOYSA-N
InChI=1S/C38H38N4O6.2CH4O3S/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;2*1-5(2,3)4/h5-12,17-22H,13-16,23H2,1-4H3,(H,40,44)(H,41,43);2*1H3,(H,2,3,4)
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
DescriptionCurator'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
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.
Originator
Curator's Comment: In August 2001, Xenova signed an exclusive licence agreement with Vancouver-based QLT Inc under the term of which QLT Inc have assumed responsibility for the further development and marketing of tariquidar in the United States, Canada and Mexico. Xenova retains substantially all commercial rights to tariquidar outside the United States, Canada and Mexico, including European and Rest of World marketing rights.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Modulation of drug resistance transporters as a strategy for treating myelodysplastic syndrome. | 2004 Dec |
|
| Synthesis and structure-activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein. | 2011 Aug 25 |
|
| Increasing oxime efficacy by blood-brain barrier modulation. | 2011 Sep 25 |
|
| Inhibition of P-glycoprotein Gene Expression and Function Enhances Triptolide-induced Hepatotoxicity in Mice. | 2015 Jul 2 |
Sample Use Guides
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
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
Edited
Fri Dec 15 16:08:10 GMT 2023
by
admin
on
Fri Dec 15 16:08:10 GMT 2023
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| Record UNII |
U2JL9545E1
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| Record Status |
Validated (UNII)
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| Record Version |
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