TOLVAPTAN

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Trade Names	JYNARQUE SAMSCA
Synonyms	Jinarc Jynarque OPC-41061 OPC-41061(TOLVAPTAN) Samsca Tolvaptan
Status
Molecule Category	UNKNOWN
ATC	C03XA01
UNII	21G72T1950
EPA CompTox	DTXSID3048780


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

Structure


InChI Key	GYHCTFXIZSNGJT-UHFFFAOYSA-N
Smiles	Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(O)c3cc(Cl)ccc32)c(C)c1
InChI	InChI=1S/C26H25ClN2O3/c1-16-6-3-4-7-20(16)25(31)28-19-10-11-21(17(2)14-19)26(32)29-13-5-8-24(30)22-15-18(27)9-12-23(22)29/h3-4,6-7,9-12,14-15,24,30H,5,8,13H2,1-2H3,(H,28,31)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H25ClN2O3
Molecular Weight	448.95
AlogP	5.68
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	3.0
Polar Surface Area	69.64
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	32.0

Bioactivity

Mechanism of Action	Action	Reference
Vasopressin V2 receptor antagonist	ANTAGONIST	DailyMed


Protein: Vasopressin V2 receptor Description: Vasopressin V2 receptor Organism : Homo sapiens P30518 ENSG00000126895

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Vasopressin and oxytocin receptor	-	0	-	0	-
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	9990	-	-	-

Assay Description	Organism	Bioactivity	Reference
Binding affinity towards AVP receptor	None	0.79 nM
Concentration which inhibit [3H]AVP binding to human Vasopressin V2 receptor coded HeLa cells by 50%	None	0.43 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-3.31 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	23.37 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	7.586 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.05 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.05 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %
Antagonist activity at human AVPR2 by PathHunter beta-arrestin assay	Homo sapiens	0.00734 nM
Displacement of [3H]-arginine-vasopressin from human V1A receptor expressed in human 1321N1 cell membranes incubated for 60 mins by radioligand binding assay	Homo sapiens	32.0 nM
Inhibition of human V1A receptor expressed in human 1321N1 cells assessed as calcium mobilization by fluorescent plate reader	Homo sapiens	470.0 nM
Displacement of [3H]-arginine-vasopressin from human V2 receptor expressed in human 1321N1 cell membranes incubated for 60 mins by radioligand binding assay	Homo sapiens	1.0 nM

Cross References

Resources	Reference
ChEBI	32246
ChEMBL	CHEMBL344159
DrugBank	DB06212
DrugCentral	4110
FDA SRS	21G72T1950
Guide to Pharmacology	2226
PubChem	216237
SureChEMBL	SCHEMBL242421
ZINC	ZINC01490477

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).