Argatroban

Summary

Argatroban (CHEMBL1166) is an approved small molecule (ATC B01AE03) targeting F2; indicated across 7 conditions including thrombotic disease and thrombocytopenia.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AE03
• Targets: 1 (F2)
• Indications: 7 conditions
• Clinical trials: 24
• Chemistry: 508.6 Da · C23H36N6O5S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1166
Name	Argatroban
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	92722
ATC	B01AE03
Molecular formula	C23H36N6O5S
Molecular weight	508.6
InChIKey	KXNPVXPOPUZYGB-IOVMHBDKSA-N

SMILES: C[C@@H]1CCN([C@H](C1)C(=O)O)C(=O)[C@H](CCCN=C(N)N)NS(=O)(=O)C2=CC=CC3=C2NCC(C3)C

IUPAC name: (2R,4R)-1-[(2S)-5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid

Also known as: Acova, Argatroban, Argatroban anhydrous, Argatroban hydrate, Argatroban in dextrose, Argatroban in sodium chloride, Argatroban monohydrate, Argipidine, DK-7419, GN-1600, GN1600, MCI-9038

Patent coverage: 153 distinct patent families (231 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 168 (73%) of the total. 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
F2	coagulation factor II, thrombin	Inhibition	7.7	1.4%	P00734

Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Tissue-type plasminogen activator, Prothrombin, Trypsin, Coagulation factor X, Serine protease 1, Prothrombin.

Bioactivity

ChEMBL activities: 32 potent at pChembl ≥ 5 of 34 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
F2	8.62	Kd	2.42	nM	CHEMBL_ACT_13414419
F2	8.41	IC50	3.88	nM	CHEMBL_ACT_15760231
F2	8.4	Ki	4	nM	CHEMBL_ACT_879656
F2	8.35	Ki	4.5	nM	CHEMBL_ACT_13414448
F2	8.27	IC50	5.4	nM	CHEMBL_ACT_2060327
F2	8.02	IC50	9.46	nM	CHEMBL_ACT_15213383
F2	8.02	IC50	9.46	nM	CHEMBL_ACT_24773420
P00735	8.02	Ki	9.6	nM	CHEMBL_ACT_698412
F2	8	Ki	10	nM	CHEMBL_ACT_1277605
F2	8	Ki	9.9	nM	CHEMBL_ACT_1405031
F2	7.97	IC50	10.6	nM	CHEMBL_ACT_13414413
F2	7.93	IC50	11.7	nM	CHEMBL_ACT_16817212
F2	7.72	Ki	19	nM	CHEMBL_ACT_346451
F2	7.72	Ki	19	nM	CHEMBL_ACT_794253
P00735	7.7	Ki	20	nM	CHEMBL_ACT_18168778
F2	7.7	Ki	20	nM	CHEMBL_ACT_933725
F2	7.42	IC50	38	nM	CHEMBL_ACT_1173527
F2	7.42	IC50	38	nM	CHEMBL_ACT_995917
F2	7.41	IC50	39	nM	CHEMBL_ACT_352647
F2	7.41	Ki	39	nM	CHEMBL_ACT_643008
F2	7.4	Ki	40	nM	CHEMBL_ACT_18168781
F2	7.28	IC50	52	nM	CHEMBL_ACT_1277612
P00735	7.21	Ki	61	nM	CHEMBL_ACT_434704
P00735	7.07	Ki	85	nM	CHEMBL_ACT_434705
F2	7.03	IC50	92.4	nM	CHEMBL_ACT_13414410
F2	6.48	IC50	331	nM	CHEMBL_ACT_1660746
F2	6.26	IC50	550	nM	CHEMBL_ACT_1054134
F2	6.22	IC50	600	nM	CHEMBL_ACT_498620
F2	5.8	IC50	1580	nM	CHEMBL_ACT_13414416
PRSS1	5.7	Ki	1990	nM	CHEMBL_ACT_13414442

Target pathways

Aggregated over 1 target gene(s): F2.

Top Reactome pathways

38 total, by targets touching each:

Pathway	Targets	Genes
Hemostasis	1	F2
R-HSA-140837	1	F2
R-HSA-140875	1	F2
R-HSA-140877	1	F2
Gamma-carboxylation of protein precursors	1	F2
Transport of gamma-carboxylated protein precursors from the endoplasmic reticulum to the Golgi apparatus	1	F2
Removal of aminoterminal propeptides from gamma-carboxylated proteins	1	F2
Gamma-carboxylation, transport, and amino-terminal cleavage of proteins	1	F2
Signal Transduction	1	F2
Gamma carboxylation, hypusinylation, hydroxylation, and arylsulfatase activation	1	F2
Disease	1	F2
Complement cascade	1	F2
Innate Immune System	1	F2
Immune System	1	F2
Cell surface interactions at the vascular wall	1	F2
Signaling by GPCR	1	F2
Class A/1 (Rhodopsin-like receptors)	1	F2
Peptide ligand-binding receptors	1	F2
Regulation of Insulin-like Growth Factor (IGF) transport and uptake by Insulin-like Growth Factor Binding Proteins (IGFBPs)	1	F2
GPCR downstream signalling	1	F2
Metabolism of proteins	1	F2
G alpha (q) signalling events	1	F2
Thrombin signalling through proteinase activated receptors (PARs)	1	F2
GPCR ligand binding	1	F2
Post-translational protein modification	1	F2
Platelet activation, signaling and aggregation	1	F2
Platelet Aggregation (Plug Formation)	1	F2
R-HSA-9651496	1	F2
Defective factor XII causes hereditary angioedema	1	F2
Defective factor VIII causes hemophilia A	1	F2

Dominant GO biological processes

GO term	Targets
proteolysis	1
acute-phase response	1
cell surface receptor signaling pathway	1
blood coagulation	1
positive regulation of cell population proliferation	1
regulation of cell shape	1
response to wounding	1
negative regulation of platelet activation	1
platelet activation	1
regulation of blood coagulation	1
positive regulation of blood coagulation	1
negative regulation of blood coagulation	1
positive regulation of cell growth	1
positive regulation of insulin secretion	1
positive regulation of collagen biosynthetic process	1

Indications & clinical

Indications

7 indications (3 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
thrombotic disease	4	MONDO:0000831	HP:0004419
thrombocytopenia	4	MONDO:0002049	HP:0001873
intermediate coronary syndrome	2	MONDO:0006805	EFO:1000985
hemorrhagic disease	2	MONDO:0002243	MONDO:0002243
coronary artery disorder	2	MONDO:0005010	EFO:0001645

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

Clinical trials

Total trials: 24.

Phase distribution

Phase	Trials
PHASE4	10
PHASE3	4
PHASE2	4
Not specified	3
PHASE2/PHASE3	1
PHASE1/PHASE2	1
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00035178	PHASE4	COMPLETED	Pharmacokinetics/Pharmacodynamics of Argatroban Injection in End-Stage Renal Disease Patients Undergoing Hemodialysis
NCT00039858	PHASE4	COMPLETED	Evaluation of Argatroban Injection in Pediatric Patients Requiring Anticoagulant Alternatives to Heparin
NCT00798525	PHASE4	TERMINATED	Argatroban Versus Lepirudin in Critically Ill Patients
NCT01163604	PHASE4	COMPLETED	Argatroban for Preventing Occlusion and Restenosis After Intracranial and Extracranial Artery Stenting
NCT01246011	PHASE4	TERMINATED	Significance of Antibodies to Heparin/Platelet Factor 4 Complex in Vein Graft Patency and Potential Role of Argatroban for Prevention of Vein Graft Occlusion
NCT01980316	PHASE4	COMPLETED	Argatroban for Preventing Occlusion and Restenosis After Extracranial Vertebral Artery Stenting
NCT03740958	PHASE4	COMPLETED	Argatroban Plus R-tPA for Acute Ischemic Stroke
NCT04275180	PHASE4	COMPLETED	Efficacy Argatroban in Ischemic Stroke With Early Deterioration (EASE)
NCT04406389	PHASE4	TERMINATED	Anticoagulation in Critically Ill Patients With COVID-19 (The IMPACT Trial)
NCT05740371	PHASE4	COMPLETED	Safety of Argatroban Infusion in Conduction Disturbances
NCT00198588	PHASE3	COMPLETED	Efficacy and Safety Study of Argatroban to Treat Heparin-Induced Thrombocytopenia
NCT02935530	PHASE3	COMPLETED	Thromboprophylaxis After Surgery for Gynecologic Malignancy in China
NCT03735979	PHASE3	COMPLETED	Multi-arm Optimization of Stroke Thrombolysis
NCT03809481	PHASE3	TERMINATED	Open-Label, Randomised, Active Controlled, Multi-Centre Phase 3 Study Safety and Efficacy of Danaparoid vs Argatroban
NCT05226442	PHASE2/PHASE3	COMPLETED	Safety and Feasibility of Argatroban As Anticoagulant in Adults with ECMO
NCT00268762	PHASE1/PHASE2	COMPLETED	Argatroban Stroke Treatment - A Pilot Safety Study
NCT00508924	PHASE2	COMPLETED	Study on Safety and Effectiveness of Three Doses of Argatroban as Anticoagulant in Percutaneous Coronary Intervention (PCI)
NCT00861692	PHASE2	COMPLETED	Clinical Management of Argatroban in Patients With Heparin Induced Thrombocytopenia Type II
NCT01734252	PHASE2	COMPLETED	Argatroban in Critically Ill Patients With Heparin Resistance
NCT02448069	PHASE2	COMPLETED	Safety and Feasibility of Argatroban, Tissue Plasminogen Activator and Intra-arterial Therapy in Stroke
NCT05325346	PHASE1	COMPLETED	A Phase I Study of the Co-administration of VLX-1005 and Argatroban in Healthy Human Subjects
NCT01304238	Not specified	COMPLETED	Retrospective Registry of Patients With Acute Heparin-induced Thrombocytopenia Type II
NCT04925167	Not specified	COMPLETED	Safety and Efficacy of Argatroban Applicated in Anticoagulation of V-V ECMO
NCT06038682	Not specified	COMPLETED	Monitoring Anticoagulation in Patients on ECMO for Severe Lung Failure

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

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.

50 molecules share ≥1 primary target. Top 50 by shared-target count:

Molecule	Source	Status	Shared targets
APIXABAN	ChEMBL + PubChem	Phase 4 (approved)	F2
EDOXABAN	ChEMBL + PubChem	Phase 4 (approved)	F2
BENZOYL PEROXIDE	ChEMBL	Phase 4 (approved)	F2
BETRIXABAN	ChEMBL	Phase 4 (approved)	F2
BIVALIRUDIN	ChEMBL	Phase 4 (approved)	F2
BORTEZOMIB	ChEMBL	Phase 4 (approved)	F2
CAPTOPRIL	ChEMBL	Phase 4 (approved)	F2
CIANIDANOL	ChEMBL	Phase 4 (approved)	F2
DABIGATRAN ETEXILATE	ChEMBL	Phase 4 (approved)	F2
DEQUALINIUM	ChEMBL	Phase 4 (approved)	F2
GENTIAN VIOLET	ChEMBL	Phase 4 (approved)	F2
HEXAMIDINE	ChEMBL	Phase 4 (approved)	F2
INDIGOTINDISULFONATE	ChEMBL	Phase 4 (approved)	F2
LIOTHYRONINE	ChEMBL	Phase 4 (approved)	F2
LUSUTROMBOPAG	ChEMBL	Phase 4 (approved)	F2
MELAGATRAN	ChEMBL	Phase 4 (approved)	F2
METHYLPREDNISOLONE	ChEMBL	Phase 4 (approved)	F2
PENTAMIDINE	ChEMBL	Phase 4 (approved)	F2
RIVAROXABAN	ChEMBL	Phase 4 (approved)	F2
SUCCIMER	ChEMBL	Phase 4 (approved)	F2
SULFAGUANIDINE	ChEMBL	Phase 4 (approved)	F2
TELOTRISTAT	ChEMBL	Phase 4 (approved)	F2
XIMELAGATRAN	ChEMBL	Phase 4 (approved)	F2
CAMOSTAT	ChEMBL	Phase 3	F2
CAMOSTAT MESILATE	ChEMBL	Phase 3	F2
DABIGATRAN	ChEMBL	Phase 3	F2
GABEXATE	ChEMBL	Phase 3	F2
MILVEXIAN	ChEMBL	Phase 3	F2
NAFAMOSTAT	ChEMBL	Phase 3	F2
QUERCETIN	ChEMBL	Phase 3	F2
SILIBININ	ChEMBL	Phase 3	F2
BMS-986141	ChEMBL	Phase 2	F2
CETRAXATE	ChEMBL	Phase 2	F2
DIBROMPROPAMIDINE	ChEMBL	Phase 2	F2
EFEGATRAN	ChEMBL	Phase 2	F2
FIDEXABAN	ChEMBL	Phase 2	F2
GW813893	ChEMBL	Phase 2	F2
INOGATRAN	ChEMBL	Phase 2	F2
LETAXABAN	ChEMBL	Phase 2	F2
NAPSAGATRAN	ChEMBL	Phase 2	F2
PROFLAVINE	ChEMBL	Phase 2	F2
RAZAXABAN	ChEMBL	Phase 2	F2
SEGATROXABAN	ChEMBL	Phase 2	F2
TANOGITRAN	ChEMBL	Phase 2	F2
Echothiophate	PubChem	Approved	F2
Pimavanserin	PubChem	Approved	F2
Propylene Glycol	PubChem	Approved	F2
Pyrazinamide	PubChem	Approved	F2
Pyridoxine	PubChem	Approved	F2
Vorapaxar	PubChem	Approved	F2