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Compound Detail

CHEMBL348475

TARIQUIDAR
🧪 Phase III
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🧪 Phase III
COc1cc2c(cc1OC)CN(CCc1ccc(NC(=O)c3cc(OC)c(OC)cc3NC(=O)c3cnc4ccccc4c3)cc1)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL348475
Name TARIQUIDAR
Phase Phase III
Structure Type MOL
InChI Key LGGHDPFKSSRQNS-UHFFFAOYSA-N

Known Names

Tariquidar XR-9576 XR9576
31
Targets
145
Activities
2
Assay Types
21
PK Parameters
20
Publications
3
Known Names
6
Indications
1
Mechanisms

Molecular Properties

646.7
MW (Da)
6.37
ALogP
8
HBA
2
HBD
111.2
PSA (Ų)
0.17
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -dar
USAN Year 2002

Extended Properties

Molecular Formula C38H38N4O6
MW 646.74
Aromatic Rings 5
Heavy Atoms 48
NP-Likeness -1.07

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
P-glycoprotein 1 inhibitor INHIBITOR ATP-dependent translocase ABCB1 ✓ ✓

Indications

Carcinoma, Non-Small-Cell Lung Adrenal Cortex Neoplasms Breast Neoplasms Lung Neoplasms Neuralgia Ovarian Neoplasms

Activity Summary

IC50 133 meas. best 9.59
EC50 12 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 9.59 6.9997 0.3 39
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.39 7.9614 0.4 7
KB 3-1
CHEMBL614590
 IC50 8.98 8.51 1.0 3
HEK293
CHEMBL614818
 IC50 8.82 8.2671 1.5 7
KB-V1
CHEMBL4296451
 IC50 8.67 8.3833 2.1 3
OVCAR-8
CHEMBL612555
 IC50 8.58 8.1567 2.6 3
Unchecked
CHEMBL612545
 IC50 8.2 6.6074 6.3 19
NCI/ADR-RES
CHEMBL613829
 IC50 8.17 6.5111 6.8 9
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 EC50 8.0 7.6667 10.0 3
Eca-109/VCR
CHEMBL6066735
 IC50 7.94 7.94 11.4 1
ATP-dependent translocase ABCB1
CHEMBL4302
 EC50 7.8 7.3129 16.0 7
MDR
CHEMBL614125
 EC50 7.79 7.79 16.3 1
NCI/ADR-RES
CHEMBL613829
 EC50 7.73 7.73 18.7 1
ECa-109 cell line
CHEMBL614668
 IC50 7.44 7.44 36.5 1
EMT6
CHEMBL614294
 IC50 7.42 7.42 38.0 1
ATP-dependent translocase ABCB1
CHEMBL3467
 IC50 7.19 7.19 64.0 2
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.74 6.1277 183.3 13
ADMET
CHEMBL612558
 IC50 5.89 5.03 1280.0 3
HEK-293T
CHEMBL3706568
 IC50 5.28 5.28 5220.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.15 5.15 7100.0 1
HK-2
CHEMBL4296428
 IC50 5.09 5.09 8030.0 1
MCF7
CHEMBL387
 IC50 5.09 5.09 8110.0 1
HCT-116
CHEMBL394
 IC50 4.9 4.9 12500.0 1
K562
CHEMBL385
 IC50 4.74 4.58 18420.0 3
Multidrug resistance-associated protein 1
CHEMBL3004
 IC50 4.62 4.62 23780.0 1
SW-620
CHEMBL612262
 IC50 4.6 4.6 25000.0 1
Hepatocyte
CHEMBL613289
 IC50 4.6 4.6 25000.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.57 4.57 27200.0 1
K562/A02
CHEMBL4296448
 IC50 4.57 4.5533 27190.0 3
HepG2
CHEMBL395
 IC50 4.43 4.43 37200.0 1
HUVEC
CHEMBL613979
 IC50 4.39 4.39 40260.0 1
Cytochrome P450 2C8
CHEMBL3721
 IC50 4.34 4.34 45300.0 1
MDCK-II
CHEMBL4296466
 IC50 4.08 4.08 83640.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 257.0 ng.hr.mL-1 Mus musculus
AUC 265.0 ng.hr.mL-1 Mus musculus
AUC 2963.0 ng.hr.mL-1 Rattus norvegicus
AUC 3022.0 ng.hr.mL-1 Rattus norvegicus
CL 23.0 mL.min-1.g-1 Homo sapiens
CL 23.0 mL.min-1.g-1 Rattus norvegicus
CL 23.0 mL.min-1.g-1 Mus musculus
CL 39.0 mL.min-1.g-1 Macaca mulatta
Cmax 361.81 nM Mus musculus
Cmax 800.94 nM Rattus norvegicus
MRT 1.26 hr Mus musculus
MRT 5.82 hr Rattus norvegicus
T1/2 3.5 hr Rattus norvegicus
T1/2 1.11 hr Mus musculus
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Rattus norvegicus
T1/2 1.0 hr Mus musculus
T1/2 0.5833 hr Macaca mulatta
T1/2 4.71 hr Rattus norvegicus
Tmax 0.8 hr Mus musculus
Tmax 4.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ATP-dependent translocase ABCB1 IC50 = 0.26 nM 9.59 Reversal of P-glycoprotein mediated multidrug resistance in human MCF-7T cells a... 33360797
NON-PROTEIN TARGET IC50 = 0.41 nM 9.39 Potentiation of vincristine-induced cytotoxicity against human KB-3-1 cells asse... 27504669
ATP-dependent translocase ABCB1 IC50 = 0.66 nM 9.18 Inhibition of human ABCB1 expressed in KBV1 cells assessed as potentiation of vi... 27504669
ATP-dependent translocase ABCB1 IC50 = 0.71 nM 9.15 Reversal of P-glycoprotein mediated multidrug resistance in human MCF-7T cells a... 33360797
KB 3-1 IC50 = 1.04 nM 8.98 Chemo-sensitizing activity against human KB 3-1 cells assessed as vincristine IC... 34496204
HEK293 IC50 = 1.52 nM 8.82 Chemo-sensitizing activity against human HEK293 cells assessed as vincristine IC... 34496204
ATP-dependent translocase ABCB1 IC50 = 2.05 nM 8.69 Reversal of P-glycoprotein mediated multidrug resistance in human KBV cells asse... 33360797
KB-V1 IC50 = 2.13 nM 8.67 Chemo-sensitizing activity against ABCB1-expressing human KB-V1 cells assessed a... 34496204
KB-V1 IC50 = 2.22 nM 8.65 Chemo-sensitizing activity against ABCB1-overexpressing human KB-V1 cells assess... 34496204
KB 3-1 IC50 = 2.45 nM 8.61 Chemo-sensitizing activity against human KB 3-1 cells assessed as paclitaxel IC5... 34496204
HEK293 IC50 = 2.55 nM 8.59 Chemo-sensitizing activity against human HEK293 cells assessed as paclitaxel IC5... 34496204
OVCAR-8 IC50 = 2.61 nM 8.58 Chemo-sensitizing activity against human OVCAR-8 cells assessed as paclitaxel IC... 34496204
HEK293 IC50 = 3.21 nM 8.49 Chemo-sensitizing activity against ABCB1-overexpressing human HEK293/MDR19 cells... 34496204
ATP-dependent translocase ABCB1 IC50 = 3.26 nM 8.49 Reversal of P-glycoprotein mediated multidrug resistance in human MCF-7T cells a... 33360797
ATP-dependent translocase ABCB1 IC50 = 3.34 nM 8.48 Reversal of P-glycoprotein mediated multidrug resistance in human KBV cells asse... 33360797
HEK293 IC50 = 4.24 nM 8.37 Chemo-sensitizing activity against ABCB1-overexpressing human HEK293/MDR19 cells... 34496204
OVCAR-8 IC50 = 4.62 nM 8.34 Chemo-sensitizing activity against human OVCAR-8 cells assessed as vincristine I... 34496204
NON-PROTEIN TARGET IC50 = 4.95 nM 8.3 Potentiation of doxorubicin-induced cytotoxicity against HEK293 cells assessed a... 27504669
NON-PROTEIN TARGET IC50 = 5.18 nM 8.29 Potentiation of vincristine-induced cytotoxicity against human OVCAR8 cells asse... 27504669
Unchecked IC50 = 6.28 nM 8.2 Potentiation of vincristine-induced cytotoxicity against human KBV cells assesse... 35219948

Literature References

PubMed DOI Target Context # Activities
38762918 10.1016/j.ejmech.2024.116492 ADMET 30
27504669 10.1021/acs.jnatprod.6b00597 ATP-dependent translocase ABCB1 18
38762918 10.1016/j.ejmech.2024.116492 ATP-dependent translocase ABCB1 18
34496204 10.1021/acs.jnatprod.1c00584 HEK293 12
28645831 10.1016/j.bmc.2017.06.015 ATP-dependent translocase ABCB1 12
31202598 10.1016/j.bmc.2019.06.013 Unchecked 12
38784466 10.1039/d4md00136b Eca-109/VCR 11
27504669 10.1021/acs.jnatprod.6b00597 KB 3-1 8
27328029 10.1021/acs.jmedchem.6b00605 ATP-dependent translocase ABCB1 8
35219948 10.1016/j.ejmech.2022.114207 Unchecked 8
33360797 10.1016/j.ejmech.2020.113107 ATP-dependent translocase ABCB1 8
27504669 10.1021/acs.jnatprod.6b00597 NON-PROTEIN TARGET 7
38103540 10.1016/j.ejmech.2023.116039 Unchecked 7
26197160 10.1016/j.ejmech.2015.06.049 ADMET 7
29631786 10.1016/j.bmc.2018.03.045 Unchecked 6
34496204 10.1021/acs.jnatprod.1c00584 OVCAR-8 6
34496204 10.1021/acs.jnatprod.1c00584 KB-V1 6
34496204 10.1021/acs.jnatprod.1c00584 KB 3-1 6
34496204 10.1021/acs.jnatprod.1c00584 NCI/ADR-RES 6
18083034 10.1016/j.bmc.2007.11.057 ATP-dependent translocase ABCB1 5

Data from ChEMBL 36 via Core Engine