Compound Detail

CHEMBL48361

DABIGATRAN

🧪 Phase III

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🧪 Phase III

Cn1c(CNc2ccc(C(=N)N)cc2)nc2cc(C(=O)N(CCC(=O)O)c3ccccn3)ccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL48361
Name	DABIGATRAN
Phase	Phase III
Structure Type	MOL
InChI Key	YBSJFWOBGCMAKL-UHFFFAOYSA-N

Known Names

BIBR 953 ZW BIBR-953 BIBR-953-ZW Dabigatran Pradaxa (dabigatran)

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

471.5

MW (Da)

2.99

ALogP

HBA

HBD

150.2

PSA (Å²)

0.22

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

USAN Stem	-gatran
USAN Year	2008

Extended Properties

Molecular Formula	C25H25N7O3
MW	471.52
Aromatic Rings	4
Heavy Atoms	35
NP-Likeness	-1.54

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Thrombin inhibitor	INHIBITOR	Prothrombin	✓	✓

Indications

Atrial Fibrillation Hematoma Stroke Thromboembolism Venous Thromboembolism Wounds and Injuries CADASIL Hemorrhage Ischemic Stroke Renal Insufficiency Respiratory Syncytial Virus Infections

Activity Summary

IC50 22 meas. best 8.92

Ki 17 meas. best 8.35

EC50 3 meas. best 8.15

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Prothrombin CHEMBL204	IC50	8.92	8.4236	1.2	14
Prothrombin CHEMBL204	Ki	8.35	8.3071	4.5	7
Unchecked CHEMBL612545	EC50	8.15	7.845	7.0	2
Unchecked CHEMBL612545	IC50	7.86	6.885	13.8	2
Unchecked CHEMBL612545	Ki	7.3	7.3	50.0	1
Trypsin CHEMBL2095204	Ki	7.3	7.3	50.0	2
Plasma CHEMBL613424	EC50	6.52	6.52	300.0	1
Plasma CHEMBL613589	IC50	6.22	6.22	600.0	1
Serine protease hepsin CHEMBL2079849	Ki	6.08	6.08	835.0	1
Plasminogen CHEMBL1801	Ki	5.77	5.77	1695.0	1
Coagulation factor X CHEMBL244	Ki	5.42	5.42	3760.0	2
Solute carrier family 22 member 2 CHEMBL1743122	IC50	5.33	5.33	4700.0	1
Coagulation factor X CHEMBL244	IC50	5.24	5.24	5800.0	1
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	5.09	5.09	8100.0	1
Ribosyldihydronicotinamide dehydrogenase [quinone] CHEMBL3959	IC50	4.96	4.96	11000.0	1
Vitamin K-dependent protein C CHEMBL4444	Ki	4.68	4.68	20930.0	1
Multidrug and toxin extrusion protein 2 CHEMBL1743127	IC50	4.6	4.6	25300.0	1
Tissue-type plasminogen activator CHEMBL1873	Ki	4.34	4.34	45360.0	1
Ribosyldihydronicotinamide dehydrogenase [quinone] CHEMBL3959	Ki	4.22	4.22	60000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
F	6.5	%	Homo sapiens
T1/2	0.2533	hr	Homo sapiens
Tmax	0.425	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Prothrombin	IC50	=	1.2	nM	8.92	Inhibition of human thrombin pre-incubated for 10 mins before Ac-FVR-AMC substra...	27187866
Prothrombin	IC50	=	1.2	nM	8.92	Inhibition of human thrombin preincubated for 10 mins followed by Ac-FVR-AMC sub...	27951488
Prothrombin	IC50	=	1.23	nM	8.91	Inhibition of human thrombin preincubated for 10 mins followed by Ac-FVR-AMC sub...	27166573
Prothrombin	IC50	=	1.23	nM	8.91	Inhibition of human thrombin preincubated for 10 mins followed by Ac-FVR-AMC sub...	27166573
Prothrombin	IC50	=	2.2	nM	8.66	Inhibition of human thrombin using tosyl-glycyl-prolyl-arginine-4-nitranilide ac...	26537784
Prothrombin	IC50	=	2.61	nM	8.58	Inhibition of human thrombin using Ac-FVR-AMC as substrate incubated for 10 mins...	25874337
Prothrombin	IC50	=	2.63	nM	8.58	Inhibition of thrombin (unknown origin)	26690913
Prothrombin	IC50	=	2.61	nM	8.58	Inhibition of thrombin in human blood using fluorogenic Ac-FVR-AMC as substrate ...	34902735
Prothrombin	Ki	=	4.5	nM	8.35	Inhibition of human thrombin using tosyl-glycyl-prolyl-arginine-4-nitranilide ac...	29072911
Prothrombin	Ki	=	4.5	nM	8.35	Inhibition of human coagulation factor alpha-thrombin using Boc-Val-Pro-Arg-AMC ...	33089691
Prothrombin	Ki	=	4.5	nM	8.35	Inhibitory constant (Ki) was determined against human thrombin	11960487
Prothrombin	Ki	=	4.5	nM	8.35	Binding affinity to human thrombin	23043765
Prothrombin	Ki	=	4.5	nM	8.35	Inhibition of thrombin (unknown origin)	24175584
Prothrombin	IC50	=	6.0	nM	8.22	Inhibition of human thrombin assessed as reduction in release of free nitroanili...	27884512
Prothrombin	Ki	=	6.3	nM	8.2	Inhibition of thrombin using S-2238 as substrate preincubated for 15 mins prior ...	22365562
Prothrombin	Ki	=	6.3	nM	8.2	Inhibition of thrombin (unknown origin) using S-2238 as substrate incubated for ...	23644213
Prothrombin	IC50	=	6.4	nM	8.19	Inhibition of human coagulation factor alpha-thrombin using Boc-Val-Pro-Arg-AMC ...	33089691
Unchecked	EC50	=	7.0	nM	8.15	Inhibition of thrombin induced platelet activation in CD-1 mouse plasma incubate...	36462436
Prothrombin	IC50	=	9.3	nM	8.03	Inhibition of human thrombin using tosyl-glycyl-prolyl-arginine-4-nitranilide ac...	29407959
Prothrombin	IC50	=	9.3	nM	8.03	Inhibition of human thrombin by chromogenic assay	11960487

Literature References

PubMed	DOI	Target Context	# Activities
22494098	10.1021/jm3001339	Ribosyldihydronicotinamide dehydrogenase [quinone]	12
33089691	10.1021/acs.jmedchem.0c01635	Plasma	4
36462436	10.1016/j.ejmech.2022.114855	Unchecked	3
24175584	10.1021/jm4005835	Plasma	3
33089691	10.1021/acs.jmedchem.0c01635	Prothrombin	3
33089691	10.1021/acs.jmedchem.0c01635	Coagulation factor XII	3
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	2
37468498	10.1038/s41467-023-40064-9	Estrogen receptor	2
36462436	10.1016/j.ejmech.2022.114855	ADMET	2
37468498	10.1038/s41467-023-40064-9	Progesterone receptor	2
11960487	10.1021/jm0109513	Prothrombin	2
33089691	10.1021/acs.jmedchem.0c01635	Coagulation factor X	2
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	2
37468498	10.1038/s41467-023-40064-9	Gamma-aminobutyric acid receptor subunit alpha-1	2
37468498	10.1038/s41467-023-40064-9	Peroxisome proliferator-activated receptor gamma	2
33089691	10.1021/acs.jmedchem.0c01635	Unchecked	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
33089691	10.1021/acs.jmedchem.0c01635	Blood	2
27166573	10.1016/j.bmc.2016.04.038	Prothrombin	2

Data from ChEMBL 36 via Core Engine