BETRIXABAN

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Search structure


Trade Names	BEVYXXA
Synonyms	Betrixaban Betrixaban maleate Bevyxxa PRT-054021 PRT054021
Status
Molecule Category	UNKNOWN
ATC	B01AF04
UNII	74RWP7W0J9


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

Structure


InChI Key	XHOLNRLADUSQLD-UHFFFAOYSA-N
Smiles	COc1ccc(NC(=O)c2ccc(C(=N)N(C)C)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1
InChI	InChI=1S/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C23H22ClN5O3
Molecular Weight	451.91
AlogP	4.14
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	6.0
Polar Surface Area	107.41
Molecular species	BASE
Aromatic Rings	3.0
Heavy Atoms	32.0

Bioactivity

Mechanism of Action	Action	Reference
Coagulation factor X inhibitor	INHIBITOR	PubMed PubMed


Protein: Coagulation factor X Description: Coagulation factor X Organism : Homo sapiens P00742 ENSG00000126218

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily	-	18-18000	-	0-0	-
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	8900-8900	-	1800	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of Factor 10a	None	1.5 nM		Inhibition of Factor 10a	None	0.117 nM
Inhibition of factor 10a	None	0.12 nM
Inhibition of human factor 10a using substrate S-2765 preincubated for 30 mins followed by substrate addition measured after 20 mins by micro plate reader method	Homo sapiens	4.5 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	-1.76 %
Inhibition of human factor Xa using S-2222 as substrate preincubated for 30 mins followed by substrate addition and measured for 20 mins	Homo sapiens	4.5 nM
Inhibition of human recombinant thrombin expressed in HEK293 cells using S-2238 as substrate preincubated for 30 mins followed by substrate addition and measured for 20 mins	Homo sapiens	18.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.04 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.906 %
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	-0.16 %		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	-0.16 %		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 %

Cross References

Resources	Reference
ChEBI	140421
ChEMBL	CHEMBL512351
DrugBank	DB12364
DrugCentral	5241
FDA SRS	74RWP7W0J9
Guide to Pharmacology	9602
PubChem	10275777
SureChEMBL	SCHEMBL158591
ZINC	ZINC000030691754

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).