ZOSUQUIDAR

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Search structure


Synonyms	Zosuquidar
Status
Molecule Category	Free-form
UNII	AB5K82X98Y
EPA CompTox	DTXSID9057894


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	IHOVFYSQUDPMCN-DBEBIPAYSA-N
Smiles	O[C@@H](COc1cccc2ncccc12)CN1CCN([C@@H]2c3ccccc3[C@@H]3[C@H](c4ccccc42)C3(F)F)CC1
InChI	InChI=1S/C32H31F2N3O2/c33-32(34)29-22-7-1-3-9-24(22)31(25-10-4-2-8-23(25)30(29)32)37-17-15-36(16-18-37)19-21(38)20-39-28-13-5-12-27-26(28)11-6-14-35-27/h1-14,21,29-31,38H,15-20H2/t21-,29-,30+,31-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C32H31F2N3O2
Molecular Weight	527.62
AlogP	5.21
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	6.0
Polar Surface Area	48.83
Molecular species	NEUTRAL
Aromatic Rings	4.0
Heavy Atoms	39.0

Bioactivity

Mechanism of Action	Action	Reference
P-glycoprotein 1 inhibitor	INHIBITOR	PubMed PubMed


Protein: P-glycoprotein 1 Description: ATP-dependent translocase ABCB1 Organism : Homo sapiens P08183 ENSG00000085563

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	59	-	-	40-58

Assay Description	Organism	Bioactivity	Reference
Intrinsic cytotoxicity against mouse NIH/3T3 cells overexpressing MDR1 at 10 uM after 72 hrs by MTT assay	Mus musculus	3.1 %
Intrinsic cytotoxicity against mouse NIH/3T3 cells overexpressing MDR1 at 3 uM after 72 hrs by MTT assay	Mus musculus	3.1 %
Intrinsic cytotoxicity against wild type mouse NIH/3T3 cells at 10 uM after 72 hrs by MTT assay	Mus musculus	2.4 %
Intrinsic cytotoxicity against wild type mouse NIH/3T3 cells at 3 uM after 72 hrs by MTT assay	Mus musculus	2.4 %
Inhibition of P-glycoprotein-mediated daunorubicin efflux from human CCRF-CEM/VCR1000 cells after 240 secs by FACS flow cytometric analysis	Homo sapiens	58.88 nM
Inhibition of human P-gp expressed in high five insect cell membrane vesicles by measuring the vanadate-sensitive ATPase activity of P-gp at 0.05 uM preincubated for 5 mins in the presence of sodium orthovanadate measured after 20 mins by colorimetric method	Homo sapiens	40.0 %
Inhibition of human P-gp expressed in high five insect cell membrane vesicles by measuring the vanadate-sensitive ATPase activity of P-gp at 0.5 uM preincubated for 5 mins in the presence of sodium orthovanadate measured after 20 mins by colorimetric method	Homo sapiens	58.0 %
Binding affinity to P-gp (unknown origin)	Homo sapiens	100.0 nM
Reversal of resistance to paclitaxel-induced cytotoxicity in human SW-620/AD300 cells assessed as reduction in paclitaxel IC50 at 2 uM preincubated for 4 hrs followed by paclitaxel addition and measured after 72 hrs by MTT assay (Rvb = 4.23 +/- 0.50 uM)	Homo sapiens	59.0 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL444172
DrugBank	DB06191
FDA SRS	AB5K82X98Y
PDB	ZQU
SureChEMBL	SCHEMBL12432743
ZINC	ZINC000100029945

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).