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Compound Detail

CHEMBL512351

BETRIXABAN
💊 Approved Drug
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💊 Approved Drug
COc1ccc(NC(=O)c2ccc(C(=N)N(C)C)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL512351
Name BETRIXABAN
Phase Approved
Structure Type MOL
InChI Key XHOLNRLADUSQLD-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Betrixaban Betrixaban maleate Bevyxxa PRT-054021 PRT054021
4
Targets
12
Activities
2
Assay Types
30
PK Parameters
20
Publications
5
Known Names
8
Indications
1
Mechanisms

Molecular Properties

451.9
MW (Da)
4.14
ALogP
5
HBA
3
HBD
107.4
PSA (Ų)
0.39
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2017
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -xaban
USAN Year 2007

Extended Properties

Molecular Formula C23H22ClN5O3
MW 451.91
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.44

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Coagulation factor X inhibitor INHIBITOR Coagulation factor X ✓ ✓

Indications

Thrombosis Venous Thromboembolism Atrial Fibrillation Atrial Flutter Hemorrhage Thromboembolism Kidney Diseases Liver Diseases

ATC Classification

B01AF04
betrixaban
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Drug Warnings

Black Box Warning
vascular toxicity
Country: United States

Activity Summary

IC50 9 meas. best 8.82
Ki 3 meas. best 9.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Coagulation factor X
CHEMBL244
 Ki 9.93 9.925 0.1 2
Coagulation factor X
CHEMBL244
 IC50 8.82 8.5067 1.5 3
Prothrombin
CHEMBL204
 IC50 7.75 5.75 18.0 3
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 5.75 5.75 1800.0 1
Unchecked
CHEMBL612545
 IC50 5.2 5.2 6300.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.05 5.05 8900.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 825.0 ng.hr.mL-1 Canis lupus familiaris
AUC 4180.0 ng.hr.mL-1 Macaca fascicularis
AUC 456.0 ng.hr.mL-1 Rattus norvegicus
AUC 571.0 ng.hr.mL-1 Rattus norvegicus
AUC 1832.0 ng.hr.mL-1 Rattus norvegicus
CL 26.5 mL.min-1.kg-1 Canis lupus familiaris
CL 18.7 mL.min-1.kg-1 Macaca fascicularis
CL 43.6 mL.min-1.kg-1 Rattus norvegicus
CL 43.6 mL.min-1.kg-1 Rattus norvegicus
CL 26.5 mL.min-1.kg-1 Canis lupus familiaris
CL 18.7 mL.min-1.kg-1 Macaca mulatta
CL 22.67 mL.min-1.kg-1 Rattus norvegicus
Cmax 323.07 nM Rattus norvegicus
F 51.6 % Canis lupus familiaris
F 58.7 % Macaca fascicularis
F 23.8 % Rattus norvegicus
F 23.8 % Rattus norvegicus
F 51.6 % Canis lupus familiaris
F 58.7 % Macaca mulatta
F 30.2 % Rattus norvegicus
Fu 0.8 - Homo sapiens
T1/2 21.2 hr Canis lupus familiaris
T1/2 9.6 hr Macaca fascicularis
T1/2 8.8 hr Rattus norvegicus
T1/2 8.6 hr Rattus norvegicus
T1/2 7.8 hr Rattus norvegicus
Tmax 2.6 hr Rattus norvegicus
Vd 48.8 L.kg-1 Canis lupus familiaris
Vd 13.4 L.kg-1 Macaca fascicularis
Vd 32.9 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Coagulation factor X Ki = 0.117 nM 9.93 Inhibition of Factor 10a 19297154
Coagulation factor X Ki = 0.12 nM 9.92 Inhibition of factor 10a 20503967
Coagulation factor X IC50 = 1.5 nM 8.82 Inhibition of Factor 10a 19297154
Coagulation factor X IC50 = 4.5 nM 8.35 Inhibition of human factor 10a using substrate S-2765 preincubated for 30 mins f... 27689724
Coagulation factor X IC50 = 4.5 nM 8.35 Inhibition of human factor Xa using S-2222 as substrate preincubated for 30 mins... 30446438
Prothrombin IC50 = 18.0 nM 7.75 Inhibition of human recombinant thrombin expressed in HEK293 cells using S-2238 ... 30446438
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 1800.0 nM 5.75 Binding affinity to human ERG 19297154
Unchecked IC50 = 6300.0 nM 5.2 Inhibition of kallikrein 19297154
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 8900.0 nM 5.05 Inhibition of human ERG expressed in HEK293 cells by patch-clamp method 19297154
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 8900.0 nM 5.05 Inhibition of human ERG by patch clamp assay 20503967
Prothrombin IC50 = 18000.0 nM 4.75 Inhibition of human thrombin using acromogenic substrate S-2238 preincubated for... 25839438
Prothrombin IC50 = 18000.0 nM 4.75 Inhibition of human thrombin using substrate S-2238 preincubated for 30 mins fol... 27689724

Literature References

PubMed DOI Target Context # Activities
30446438 10.1016/j.bmc.2018.09.012 ADMET 11
30446438 10.1016/j.bmc.2018.09.012 Rattus norvegicus 6
19297154 10.1016/j.bmcl.2009.02.111 Rattus norvegicus 5
19297154 10.1016/j.bmcl.2009.02.111 Canis familiaris 5
19297154 10.1016/j.bmcl.2009.02.111 Cynomolgus monkey 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19297154 10.1016/j.bmcl.2009.02.111 Plasma 3
20503967 10.1021/jm100146h Rhesus monkey 3
20503967 10.1021/jm100146h Canis familiaris 3
20503967 10.1021/jm100146h Rattus norvegicus 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19297154 10.1016/j.bmcl.2009.02.111 Unchecked 2
19297154 10.1016/j.bmcl.2009.02.111 Voltage-gated inwardly rectifying potassium channel KCNH2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
19297154 10.1016/j.bmcl.2009.02.111 Coagulation factor X 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
30446438 10.1016/j.bmc.2018.09.012 Plasma 2
27689724 10.1016/j.ejmech.2016.09.055 Plasma 2
27689724 10.1016/j.ejmech.2016.09.055 Rattus norvegicus 2
19297154 10.1016/j.bmcl.2009.02.111 Tissue-type plasminogen activator 1

Data from ChEMBL 36 via Core Engine