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Compound Detail

CHEMBL231779

APIXABAN
💊 Approved Drug
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💊 Approved Drug
COc1ccc(-n2nc(C(N)=O)c3c2C(=O)N(c2ccc(N4CCCCC4=O)cc2)CC3)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL231779
Name APIXABAN
Phase Approved
Structure Type MOL
InChI Key QNZCBYKSOIHPEH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Apixaban Apixaban accord BMS-562247 BMS-562247-01 Eliquis
8
Targets
31
Activities
3
Assay Types
30
PK Parameters
20
Publications
5
Known Names
20
Indications
1
Mechanisms

Molecular Properties

459.5
MW (Da)
2.70
ALogP
6
HBA
1
HBD
110.8
PSA (Ų)
0.63
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -xaban
USAN Year 2005

Extended Properties

Molecular Formula C25H25N5O4
MW 459.51
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.04

Mechanism of Action

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

Indications

Arthroplasty Atrial Fibrillation Embolism Pulmonary Embolism Stroke Thrombosis Thrombosis Venous Thromboembolism Venous Thrombosis Venous Thrombosis Acute Coronary Syndrome Anemia, Sickle Cell Aortic Valve Stenosis Atrial Flutter Hematoma Ischemia Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma Renal Insufficiency Severe Acute Respiratory Syndrome

ATC Classification

B01AF02
apixaban
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Drug Warnings

Black Box Warning
vascular toxicity
Country: United States

Activity Summary

IC50 15 meas. best 8.65
Ki 14 meas. best 10.1
EC50 2 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Coagulation factor X
CHEMBL244
 Ki 10.1 10.1 0.1 9
Coagulation factor X
CHEMBL5062
 Ki 9.77 9.77 0.2 1
Coagulation factor X
CHEMBL3755
 Ki 8.89 8.205 1.3 2
Coagulation factor X
CHEMBL244
 IC50 8.65 7.3233 2.3 3
Plasma
CHEMBL613424
 IC50 7.47 6.813 33.7 10
Unchecked
CHEMBL612545
 EC50 7.16 7.16 70.0 1
Oryctolagus cuniculus
CHEMBL374
 EC50 6.49 6.49 325.0 1
Oryctolagus cuniculus
CHEMBL374
 IC50 6.48 6.48 329.0 1
Prothrombin
CHEMBL204
 Ki 5.51 5.51 3100.0 2
SARS-CoV-2
CHEMBL4303835
 IC50 5.23 5.23 5910.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.3333 mL.min-1.kg-1 Canis lupus familiaris
CL 0.3333 mL.min-1.kg-1 Canis lupus familiaris
CL 0.3333 mL.min-1.kg-1 Canis lupus familiaris
CL 0.3333 mL.min-1.kg-1 Canis lupus familiaris
CL 0.26 L/Kg Rattus norvegicus
CL 0.018 L/Kg Pan troglodytes
CL 0.3333 mL.min-1.kg-1 Canis lupus familiaris
CL 21.0 % Canis lupus familiaris
CL 11.83 mL.min-1.kg-1 Rattus norvegicus
CL 0.3333 mL.min-1.kg-1 Canis lupus familiaris
CL 20.0 % Rattus norvegicus
CL 42.0 % Canis lupus familiaris
CL 27.0 % Homo sapiens
F 58.0 % Canis lupus familiaris
F 58.0 % Canis lupus familiaris
F 58.0 % Canis lupus familiaris
F 50.0 % Canis lupus familiaris
F 51.0 % Pan troglodytes
F 58.0 % Canis lupus familiaris
F 30.0 % Rattus norvegicus
F 70.0 % Canis lupus familiaris
F 50.0 % Homo sapiens
F 49.0 % Homo sapiens
F 70.0 % Canis lupus familiaris
F 30.0 % Rattus norvegicus
Fu 0.07 - Homo sapiens
T1/2 5.8 hr Canis lupus familiaris
T1/2 5.8 hr Canis lupus familiaris
T1/2 5.8 hr Canis lupus familiaris
T1/2 8.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Coagulation factor X Ki = 0.08 nM 10.1 Inhibition of purified human factor Xa 24951330
Coagulation factor X Ki = 0.08 nM 10.1 Inhibition of factor 10a 20503967
Coagulation factor X Ki = 0.08 nM 10.1 Inhibition of human factor 10a 20100660
Coagulation factor X Ki = 0.08 nM 10.1 Binding affinity to human coagulation factor 10a 19046881
Coagulation factor X Ki = 0.08 nM 10.1 Inhibition of Factor 10a 19297154
Coagulation factor X Ki = 0.08 nM 10.1 Inhibition of human factor 10a 18424044
Coagulation factor X Ki = 0.08 nM 10.1 Binding affinity to human F10a 17914785
Coagulation factor X Ki = 0.08 nM 10.1 Inhibition of human factor 10a 17588746
Coagulation factor X Ki = 0.08 nM 10.1 Inhibition of factor Xa (unknown origin) assessed as inhibition constant 36634753
Coagulation factor X Ki = 0.17 nM 9.77 Binding affinity to rabbit F10a 17914785
Coagulation factor X Ki = 1.3 nM 8.89 Binding affinity to rat FXa assessed as inhibition constant 38889609
Coagulation factor X IC50 = 2.26 nM 8.65 Inhibition of factor Xa (unknown origin) 36634753
Coagulation factor X Ki = 30.0 nM 7.52 In Vitro Assay: Factor Xa (human or rat): In the assay for measuring the inhibit... -
Plasma IC50 = 33.73 nM 7.47 Anticoagulant activity in 1 pM tissue factor stimulated human CTI-citrated plasm... 25978966
Plasma IC50 = 48.41 nM 7.32 Anticoagulant activity in 3 pM tissue factor stimulated human CTI-citrated plasm... 25978966
Plasma IC50 = 47.6 nM 7.32 Anticoagulant activity in 0.3 pM tissue factor stimulated human CTI-citrated pla... 25978966
Plasma IC50 = 51.33 nM 7.29 Anticoagulant activity in 0.1 pM recombinant coagulation factor 11a stimulated h... 25978966
Unchecked EC50 = 70.0 nM 7.16 Inhibition of tissue factor induced platelet activation in 76% human blood incub... 36462436
Plasma IC50 = 115.7 nM 6.94 Anticoagulant activity in 0.3 pM recombinant coagulation factor 11a stimulated h... 25978966
Plasma IC50 = 159.1 nM 6.8 Anticoagulant activity in 10 pM tissue factor stimulated human CTI-citrated plas... 25978966

Literature References

PubMed DOI Target Context # Activities
34010555 10.1021/acs.jmedchem.0c01720 ADMET 25
25978966 10.1016/j.bmcl.2015.04.057 Plasma 10
20503967 10.1021/jm100146h ADMET 10
23382458 10.1124/dmd.112.050260 ADMET 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
27663548 10.1016/j.bmc.2016.09.024 NON-PROTEIN TARGET 5
17914785 10.1021/jm070245n Canis familiaris 4
20503967 10.1021/jm100146h Canis familiaris 4
24951330 10.1016/j.bmcl.2014.05.101 Canis familiaris 4
28389110 10.1016/j.bmc.2017.03.055 Plasma 4
18424044 10.1016/j.bmcl.2008.03.092 Canis familiaris 4
20503967 10.1021/jm100146h Pan troglodytes 4
19046881 10.1016/j.bmcl.2008.11.049 Canis familiaris 4
36634753 10.1016/j.bmcl.2023.129127 Rattus norvegicus 4
28389110 10.1016/j.bmc.2017.03.055 Coagulation factor X 3
19046881 10.1016/j.bmcl.2008.11.049 Plasma 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
20503967 10.1021/jm100146h Oryctolagus cuniculus 3
20503967 10.1021/jm100146h Rattus norvegicus 3
17914785 10.1021/jm070245n ADMET 2

Data from ChEMBL 36 via Core Engine