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=C(OC)C=C2CN(CCC3=CC=C(NC(=O)C4=CC(OC)=C(OC)C=C4NC(=O)C5=CN=C6C=CC=CC6=C5)C=C3)CCC2=C1
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)
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.31 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
4 mg/kg bw 1 times / day other, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.03 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
6 mg/kg bw 1 times / day other, intravenous dose: 6 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.92 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
8 mg/kg bw 1 times / day other, intravenous dose: 8 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
14.48 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
4 mg/kg bw 1 times / day other, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
19.96 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
6 mg/kg bw 1 times / day other, intravenous dose: 6 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
18.83 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
8 mg/kg bw 1 times / day other, intravenous dose: 8 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
43 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
4 mg/kg bw 1 times / day other, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
16 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
6 mg/kg bw 1 times / day other, intravenous dose: 6 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
25 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23146816 |
8 mg/kg bw 1 times / day other, intravenous dose: 8 mg/kg bw route of administration: Intravenous experiment type: OTHER co-administered: |
TARIQUIDAR blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of P-glycoprotein Gene Expression and Function Enhances Triptolide-induced Hepatotoxicity in Mice. | 2015-07-02 |
|
| Increasing oxime efficacy by blood-brain barrier modulation. | 2011-09-25 |
|
| Synthesis and structure-activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein. | 2011-08-25 |
|
| Inhibition of P-glycoprotein (ABCB1)- and multidrug resistance-associated protein 1 (ABCC1)-mediated transport by the orally administered inhibitor, CBT-1((R)). | 2008-03-15 |
|
| Modulation of drug resistance transporters as a strategy for treating myelodysplastic syndrome. | 2004-12 |
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.
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625375-84-0
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ACTIVE MOIETY
SUBSTANCE RECORD
