Apixaban

Summary

Apixaban (CHEMBL231779) is an approved small-molecule anticoagulant (ATC B01AF02) targeting F10; indicated across 28 conditions including atrial fibrillation and stroke disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AF02
• Targets: 1 (F10)
• Indications: 28 conditions
• Clinical trials: 247
• Chemistry: 459.5 Da · C25H25N5O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL231779
Name	Apixaban
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	10182969
ChEBI	CHEBI:72296
ATC	B01AF02
Molecular formula	C25H25N5O4
Molecular weight	459.5
InChIKey	QNZCBYKSOIHPEH-UHFFFAOYSA-N

SMILES: COC1=CC=C(C=C1)N2C3=C(CCN(C3=O)C4=CC=C(C=C4)N5CCCCC5=O)C(=N2)C(=O)N

IUPAC name: 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[5,4-c]pyridine-3-carboxamide

ChEBI definition: A pyrazolopyridine that is 7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide substituted at position 1 by a 4-methoxyphenyl group and at position 6 by a 4-(2-oxopiperidin-1-yl)phenyl group. It is used for the prevention and treatment of thromboembolic diseases.

Pharmacological roles (ChEBI): anticoagulant, EC 3.4.21.6 (coagulation factor Xa) inhibitor.

Also known as: Apixaban, Apixaban accord, BMS-562247, Eliquis, apixaban, APIXABAN, SID174006823, ApixabanÊ, ApixabanÂ

Parent form; salt/anhydrous children: CHEMBL3526474

Patent coverage: 2,631 distinct patent families (9,262 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
F10	coagulation factor X	Inhibition	10.1	0%	P00742

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Equilibrative nucleoside transporter 1, Prothrombin, Coagulation factor X, Coagulation factor X, Coagulation factor X.

Bioactivity

ChEMBL activities: 18 potent at pChembl ≥ 5 of 19 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_15015112
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_1971684
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_1993536
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_2166735
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_25028375
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_2517462
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_2619914
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_3103019
F10	10.1	Ki	0.08	nM	CHEMBL_ACT_3514970
O19045	9.77	Ki	0.17	nM	CHEMBL_ACT_1993564
Q63207	8.89	Ki	1.3	nM	CHEMBL_ACT_26024762
F10	8.65	IC50	2.26	nM	CHEMBL_ACT_25028355
F10	8.15	IC50	7	nM	CHEMBL_ACT_29112132
Q63207	7.52	Ki	30	nM	CHEMBL_ACT_27591143
F10	6.68	IC50	210	nM	CHEMBL_ACT_18118196
F10	6.64	IC50	230	nM	CHEMBL_ACT_16765065
F2	5.51	Ki	3100	nM	CHEMBL_ACT_1993538
F2	5.51	Ki	3100	nM	CHEMBL_ACT_3103020

Target pathways

Aggregated over 1 target gene(s): F10.

Top Reactome pathways

12 total, by targets touching each:

Pathway	Targets	Genes
R-HSA-140834	1	F10
R-HSA-140837	1	F10
R-HSA-140875	1	F10
Gamma-carboxylation of protein precursors	1	F10
Transport of gamma-carboxylated protein precursors from the endoplasmic reticulum to the Golgi apparatus	1	F10
Removal of aminoterminal propeptides from gamma-carboxylated proteins	1	F10
Defective factor IX causes thrombophilia	1	F10
Defective cofactor function of FVIIIa variant	1	F10
Defective F9 variant does not activate FX	1	F10
Initiation of coagulation cascade	1	F10
Regulation of clotting cascade	1	F10
Amplification and propagation of coagulation cascade	1	F10

Dominant GO biological processes

GO term	Targets
proteolysis	1
blood coagulation	1
positive regulation of cell migration	1
positive regulation of TOR signaling	1
hemostasis	1

Indications & clinical

Indications

28 indications (9 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
atrial fibrillation	4	MONDO:0004981	EFO:0000275
stroke disorder	4	MONDO:0005098	EFO:0000712
pulmonary embolism	4	MONDO:0005279	EFO:0003827
venous thromboembolism	4	MONDO:0005399	EFO:0004286
thrombotic disease	4	MONDO:0000831	HP:0004419
acute coronary syndrome	3	MONDO:0005542	EFO:0005672
acute lymphoblastic leukemia	3	MONDO:0004967	EFO:0000220
aortic valve stenosis	3	MONDO:0042981	EFO:0000266
atrial flutter	3	MONDO:0005310	EFO:0003911
ischemic disease	3	MONDO:0005053	EFO:0000556
kidney failure	3	MONDO:0001106	HP:0000083
severe acute respiratory syndrome	3	MONDO:0005091	MONDO:0100096
sickle cell disease	3	MONDO:0011382	MONDO:0011382
neoplasm	3	MONDO:0005070	MONDO:0004992
chronic kidney disease	2	MONDO:0005300	EFO:0003884
patent foramen ovale	2	MONDO:0020439	HP:0001655
cirrhosis of liver	2	MONDO:0005155	EFO:0001422
heart failure	2	MONDO:0005252	EFO:0003144
nephrotic syndrome	1	MONDO:0005377	EFO:0004255
blood coagulation disease	1	MONDO:0001531	EFO:0009314

8 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 247.

Phase distribution

Phase	Trials
Not specified	74
PHASE3	54
PHASE4	49
PHASE2	34
PHASE1	29
PHASE2/PHASE3	4
EARLY_PHASE1	2
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT03129490	PHASE4	ACTIVE_NOT_RECRUITING	The Danish Non-vitamin K Antagonist Oral Anticoagulation Study in Patients With Atrial Fibrillation
NCT03129555	PHASE4	ACTIVE_NOT_RECRUITING	The Danish Non-vitamin K Antagonist Oral Anticoagulation Study in Patients With Venous Thromboembolism (DANNOAC-VTE)
NCT03568890	PHASE4	ACTIVE_NOT_RECRUITING	Short-Term Anticoagulation Versus Antiplatelet Therapy for Preventing Device Thrombosis Following Left Atrial Appendage Closure
NCT04642430	PHASE4	RECRUITING	COmparison of Bleeding Risk Between Rivaroxaban and Apixaban in Patients With Atrial Fibrillation
NCT05735639	PHASE4	RECRUITING	THRomboprophylaxis in Individuals Undergoing Superficial endoVEnous Treatment (THRIVE)
NCT06486792	PHASE4	NOT_YET_RECRUITING	Stroke Prevention In Ischemic Stroke With Covert Atrial Fibrillation
NCT06515730	PHASE4	RECRUITING	Treatment With Apixaban Versus Warfarin in Patients With Left Ventricular Thrombus After Acute Myocardial Infarction
NCT06523959	PHASE4	RECRUITING	Avoiding Risks of Thrombosis and Bleeding in Surgery (ARTS) Trial
NCT06603870	PHASE4	RECRUITING	Secondary Prevention of VTE in Patients With Cancer and Catheter-Related Upper Extremity Deep Vein Thrombosis
NCT06650501	PHASE4	RECRUITING	Dabigatran vs. Oral Anti-Xa Inhibitors in S. Aureus Bacteremia
NCT06953726	PHASE4	NOT_YET_RECRUITING	Comparing the Safety and Efficacy of Apixaban and Rivaroxaban
NCT07189897	PHASE4	RECRUITING	Apixaban or Enoxaparin After Head and Neck Cancer Surgery
NCT07237308	PHASE4	NOT_YET_RECRUITING	BEACON-AA: Apixaban With or Without Clopidogrel in Stroke Patients With Atrial Fibrillation and Cerebral Atherosclerosis
NCT07404345	PHASE4	NOT_YET_RECRUITING	Low-Dose Apixaban Added to Standard Heparin Lock Versus Heparin Lock Alone to Prevent Tunneled Hemodialysis Catheters Dysfunction (APICATH-HD)
NCT07521332	PHASE4	RECRUITING	Apixaban-PK Trial: Preventing Portal Hypertension Complications in Cirrhosis
NCT01884337	PHASE4	COMPLETED	Multi-center Study to Evaluate the Safety of Apixaban (BMS-562247) in Indian Subjects Undergoing Elective Total Knee Replacement or Total Hip Replacement Surgery
NCT01884350	PHASE4	COMPLETED	Assessment of an Education and Guidance Programme for Eliquis Adherence in Non-Valvular Atrial Fibrillation (AEGEAN)
NCT01938248	PHASE4	COMPLETED	Apixaban for the Reduction of Thrombo-Embolism in Patients With Device-Detected Sub-Clinical Atrial Fibrillation
NCT02090075	PHASE4	COMPLETED	Apixaban Versus Warfarin in the Evaluation of Progression of Atherosclerotic Calcification and Vulnerable Plaque
NCT02100228	PHASE4	COMPLETED	Study Of The Blood Thinner, Apixaban, For Patients Who Have An Abnormal Heart Rhythm (Atrial Fibrillation) And Expected To Have Treatment To Put Them Back Into A Normal Heart Rhythm (Cardioversion)
NCT02227550	PHASE4	COMPLETED	Apixaban During Atrial Fibrillation Catheter Ablation: Comparison to Vitamin K Antagonist Therapy
NCT02295475	PHASE4	COMPLETED	Apixaban for Secondary Prevention of Thromboembolism Among Patients With AntiphosPholipid Syndrome
NCT02406885	PHASE4	COMPLETED	Apixaban Pharmacokinetics in Bariatric Patients (APB)
NCT02415400	PHASE4	COMPLETED	A Study of Apixaban in Patients With Atrial Fibrillation, Not Caused by a Heart Valve Problem, Who Are at Risk for Thrombosis (Blood Clots) Due to Having Had a Recent Coronary Event, Such as a Heart Attack or a Procedure to Open the Vessels of the Heart
NCT02464969	PHASE4	COMPLETED	Apixaban for the Acute Treatment of Venous Thromboembolism in Children
NCT02559856	PHASE4	COMPLETED	Comparison of Bleeding Risk Between Rivaroxaban and Apixaban: The Pilot Study
NCT02581176	PHASE4	COMPLETED	Apixaban as Treatment of Venous Thrombosis in Patients With Cancer: The CAP Study
NCT02608099	PHASE4	COMPLETED	Apixaban Evaluation of Interrupted Or Uninterrupted Anticoagulation for Ablation of Atrial Fibrillation
NCT02666157	PHASE4	UNKNOWN	Comparison of Efficacy and Safety Among Dabigatran, Rivaroxaban, and Apixaban in Non-Valvular Atrial Fibrillation
NCT02672709	PHASE4	COMPLETED	Apixaban in Hemodialysis
NCT02935855	PHASE4	COMPLETED	ORal anticoaGulants in diAbetic and Nondiabetic Patients With nOn-valvular Atrial fibrillatioN (ORGANON)
NCT02942407	PHASE4	COMPLETED	Trial to Evaluate Anticoagulation Therapy in Hemodialysis Patients With Atrial Fibrillation
NCT02945280	PHASE4	TERMINATED	Apixaban for Routine Management of Upper Extremity Deep Venous Thrombosis
NCT02958969	PHASE4	COMPLETED	Apixaban for Primary Prevention of Venous Thromboembolism in Patients With Multiple Myeloma
NCT03196349	PHASE4	TERMINATED	Comparison of Oral Anticoagulants for Extended VEnous Thromboembolism
NCT03266783	PHASE4	COMPLETED	Comparison of Bleeding Risk Between Rivaroxaban and Apixaban for the Treatment of Acute Venous Thromboembolism
NCT03463317	PHASE4	COMPLETED	Left Atrial Appendage CLOSURE in Patients With Atrial Fibrillation Compared to Medical Therapy
NCT03590743	PHASE4	TERMINATED	Calf Deep Vein Thrombosis Treatment Trial
NCT03678506	PHASE4	TERMINATED	Apixaban for Extended Anticoagulation (APIDULCIS)
NCT03988842	PHASE4	TERMINATED	Standard-dose Apixaban AFtEr Very Low-dose ThromboLYSis for Acute Intermediate-high Risk Acute Pulmonary Embolism

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 3 clinical and 37 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

21 molecules share ≥1 primary target. Top 21 by shared-target count:

Molecule	Source	Status	Shared targets
EDOXABAN	ChEMBL + PubChem	Phase 4 (approved)	F10
ARGATROBAN	ChEMBL	Phase 4 (approved)	F10
BETRIXABAN	ChEMBL	Phase 4 (approved)	F10
FONDAPARINUX	ChEMBL	Phase 4 (approved)	F10
MELAGATRAN	ChEMBL	Phase 4 (approved)	F10
PENTAMIDINE	ChEMBL	Phase 4 (approved)	F10
RIVAROXABAN	ChEMBL	Phase 4 (approved)	F10
DABIGATRAN	ChEMBL	Phase 3	F10
DAREXABAN	ChEMBL	Phase 3	F10
GABEXATE	ChEMBL	Phase 3	F10
NAFAMOSTAT	ChEMBL	Phase 3	F10
OTAMIXABAN	ChEMBL	Phase 3	F10
EFEGATRAN	ChEMBL	Phase 2	F10
ERIBAXABAN	ChEMBL	Phase 2	F10
FIDEXABAN	ChEMBL	Phase 2	F10
GW813893	ChEMBL	Phase 2	F10
LETAXABAN	ChEMBL	Phase 2	F10
LY-517717	ChEMBL	Phase 2	F10
RAZAXABAN	ChEMBL	Phase 2	F10
SEGATROXABAN	ChEMBL	Phase 2	F10
TANOGITRAN	ChEMBL	Phase 2	F10