OTENABANT

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Search structure


Synonyms	CP-945,598 CP-945598 CP-945598-01 Cp-945598 Otenabant Otenabant hydrochloride
Status
Molecule Category	UNKNOWN
UNII	J8211Y53EF


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

Structure


InChI Key	UNAZAADNBYXMIV-UHFFFAOYSA-N
Smiles	CCNC1(C(N)=O)CCN(c2ncnc3c2nc(-c2ccccc2Cl)n3-c2ccc(Cl)cc2)CC1
InChI	InChI=1S/C25H25Cl2N7O/c1-2-31-25(24(28)35)11-13-33(14-12-25)22-20-23(30-15-29-22)34(17-9-7-16(26)8-10-17)21(32-20)18-5-3-4-6-19(18)27/h3-10,15,31H,2,11-14H2,1H3,(H2,28,35)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C25H25Cl2N7O
Molecular Weight	510.43
AlogP	4.22
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	6.0
Polar Surface Area	101.96
Molecular species	BASE
Aromatic Rings	4.0
Heavy Atoms	35.0

Bioactivity

Mechanism of Action	Action	Reference
Cannabinoid CB1 receptor antagonist	ANTAGONIST	PubMed


Protein: Cannabinoid CB1 receptor Description: Cannabinoid receptor 1 Organism : Homo sapiens P21554 ENSG00000118432

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Cannabinoid receptor	-	-	-	0-1	-

Assay Description	Organism	Bioactivity	Reference
Displacement of [3H]SR141716A from CB1 receptor in rat brain	Rattus norvegicus	2.8 nM
Displacement of [3H]SR141716A from human CB1 receptor expressed in HEK293 cells	Homo sapiens	0.7 nM
Antagonist activity against human CB1 receptor expressed in CHO-K1 cells by [35S]GTPgamma binding assay	Homo sapiens	0.12 nM
Displacement of [3H]CP55940 from human CB1 expressed in CHOK1 cell membranes	Homo sapiens	0.7 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	1.36 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	4.421 %
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	0.15 %		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	0.15 %

Cross References

Resources	Reference
ChEMBL	CHEMBL562668
DrugBank	DB11745
FDA SRS	J8211Y53EF
Guide to Pharmacology	9232
PubChem	10052040
SureChEMBL	SCHEMBL1622757
ZINC	ZINC000003948997

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).