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Compound Detail

CHEMBL1166

ARGATROBAN
💊 Approved Drug
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💊 Approved Drug
CC1CNc2c(cccc2S(=O)(=O)N[C@@H](CCCNC(=N)N)C(=O)N2CC[C@@H](C)C[C@@H]2C(=O)O)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1166
Name ARGATROBAN
Phase Approved
Structure Type MOL
InChI Key KXNPVXPOPUZYGB-IOVMHBDKSA-N
Therapeutic ✓ Yes

Known Names

Acova Argatroban Argatroban anhydrous Argatroban hydrate Argatroban in dextrose Argatroban in sodium chloride Argatroban monohydrate Argipidine DK-7419 GN-1600 GN1600 MCI-9038 +2 more
9
Targets
45
Activities
4
Assay Types
7
PK Parameters
20
Publications
14
Known Names
7
Indications
1
Mechanisms

Molecular Properties

508.6
MW (Da)
0.91
ALogP
6
HBA
6
HBD
177.7
PSA (Ų)
0.16
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2000
Availability Prescription
Chirality Racemic

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -troban
USAN Year 1997

Extended Properties

Molecular Formula C23H36N6O5S
MW 508.65
Aromatic Rings 1
Heavy Atoms 35
NP-Likeness -0.02

Mechanism of Action

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

Indications

Thrombocytopenia Thrombosis Thrombosis Ischemic Stroke Angina, Unstable Coronary Disease Hemorrhagic Disorders

ATC Classification

B01AE03
argatroban
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

IC50 24 meas. best 8.41
Ki 19 meas. best 9.0
EC50 1 meas. best 6.22
Kd 1 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.0 9.0 1.0 1
Prothrombin
CHEMBL204
 Kd 8.62 8.62 2.4 1
Prothrombin
CHEMBL204
 IC50 8.41 7.3293 3.9 15
Prothrombin
CHEMBL204
 Ki 8.4 7.8556 4.0 9
Unchecked
CHEMBL612545
 IC50 8.05 8.05 9.0 1
Prothrombin
CHEMBL4471
 Ki 8.02 7.5 9.6 4
ADMET
CHEMBL612558
 IC50 7.21 6.59 62.0 3
Plasma
CHEMBL613424
 EC50 6.22 6.22 600.0 1
Plasma
CHEMBL613424
 IC50 5.72 5.67 1900.0 2
Trypsin
CHEMBL2095204
 Ki 5.7 5.7 1990.0 1
Serine protease 1
CHEMBL3769
 Ki 5.54 5.54 2900.0 1
Serine protease 1
CHEMBL3769
 IC50 5.3 5.3 5000.0 1
Coagulation factor X
CHEMBL244
 Ki 4.28 4.28 53000.0 1
Tissue-type plasminogen activator
CHEMBL1873
 Ki 4.06 4.06 87800.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 5.0 mL.min-1.kg-1 Homo sapiens
F 27.0 % Eutheria
Fu - - Rattus norvegicus
Fu - - Homo sapiens
MRT 0.57 hr Homo sapiens
T1/2 40.0 hr Homo sapiens
T1/2 0.4 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 1.0 nM 9.0 Inhibitory activity against thrombin 15857136
Prothrombin Kd = 2.42 nM 8.62 Binding affinity to thrombin (unknown origin) by surface plasmon resonance analy... 23899618
Prothrombin IC50 = 3.88 nM 8.41 Inhibition of human thrombin using tosyl-glycyl-prolyl-arginine-4-nitranilide ac... 26537784
Prothrombin Ki = 4.0 nM 8.4 In vitro inhibition constant (Ki) against human thrombin 12904065
Prothrombin Ki = 4.5 nM 8.35 Inhibition of human thrombin 23899618
Prothrombin IC50 = 5.4 nM 8.27 Inhibition of human thrombin 17883259
Unchecked IC50 = 9.0 nM 8.05 Concentration required for 50% inhibition of thrombin induced platelet aggregati... 11454464
Prothrombin IC50 = 9.46 nM 8.02 Inhibition of human thrombin using Ac-FVR-AMC as substrate incubated for 10 mins... 25874337
Prothrombin IC50 = 9.46 nM 8.02 Inhibition of thrombin in human blood using fluorogenic Ac-FVR-AMC as substrate ... 34902735
Prothrombin Ki = 9.6 nM 8.02 Inhibitory activity against thrombin. 9301673
Prothrombin Ki = 10.0 nM 8.0 Inhibition of human alpha-thrombin. 8759623
Prothrombin Ki = 9.9 nM 8.0 Binding affinity determined against human alpha thrombin 15771442
Prothrombin IC50 = 10.6 nM 7.97 Inhibition of free thrombin (unknown origin) using S2238 as substrate 23899618
Prothrombin IC50 = 11.7 nM 7.93 Inhibition of human thrombin assessed as reduction in release of free nitroanili... 27884512
Prothrombin Ki = 19.0 nM 7.72 Inhibitory activity against thrombin. 12238922
Prothrombin Ki = 19.0 nM 7.72 Inhibitory activity against human thrombin (using Chromozym TH as the substrate) 10794696
Prothrombin Ki = 20.0 nM 7.7 Inhibition of bovine plasma thrombin using chromogenix AB as substrate after 30 ... 28850227
Prothrombin Ki = 20.0 nM 7.7 In vitro binding affinity by measuring the inhibition of human thrombin 7966150
Prothrombin IC50 = 38.0 nM 7.42 In vitro inhibitory activity against hydrolysis of human alpha thrombin 11738570
Prothrombin IC50 = 38.0 nM 7.42 In vitro inhibition of thrombin catalytic activity using s-2238 substrate at 10 ... 11738569

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
23899618 10.1016/j.bmcl.2013.07.008 Prothrombin 6
8759623 10.1021/jm9603274 Unchecked 5
30406661 10.1021/acs.jnatprod.8b00574 Mus musculus 4
12904065 10.1021/jm030025j Rattus norvegicus 4
23899618 10.1016/j.bmcl.2013.07.008 Unchecked 4
18426954 10.1124/dmd.108.020479 ADMET 4
25268757 10.1021/jm5010754 Plasma 3
15771442 10.1021/jm0303857 Unchecked 3
9171866 10.1021/jm970140s ADMET 3
9301673 10.1021/jm960668h ADMET 3
10579821 10.1021/jm9811209 Prothrombin 2
28850227 10.1021/acs.jmedchem.7b00315 Prothrombin 2
- 10.1016/S0960-894X(97)00057-7 Rattus norvegicus 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
9703466 10.1021/jm9801713 NON-PROTEIN TARGET 2
20102150 10.1021/jm901802n Rattus norvegicus 2
15771442 10.1021/jm0303857 Prothrombin 2
11738569 10.1016/s0960-894x(01)00664-3 Mus musculus 2
9171866 10.1021/jm970140s NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine