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Compound Detail

CHEMBL266349

MELAGATRAN
💊 Approved Drug
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💊 Approved Drug
N=C(N)c1ccc(CNC(=O)[C@@H]2CCN2C(=O)[C@H](NCC(=O)O)C2CCCCC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL266349
Name MELAGATRAN
Phase Approved
Structure Type MOL
InChI Key DKWNMCUOEDMMIN-PKOBYXMFSA-N

Known Names

Melagatran
12
Targets
35
Activities
4
Assay Types
12
PK Parameters
20
Publications
1
Known Names
1
Indications

Molecular Properties

429.5
MW (Da)
0.81
ALogP
5
HBA
5
HBD
148.6
PSA (Ų)
0.29
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Parenteral
USAN Stem -gatran

Extended Properties

Molecular Formula C22H31N5O4
MW 429.52
Aromatic Rings 1
Heavy Atoms 31
NP-Likeness -0.45

Indications

Thrombosis

ATC Classification

B01AE04
melagatran
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

IC50 21 meas. best 8.4
Ki 12 meas. best 8.92
EC50 1 meas. best 6.4
Kd 1 meas. best 8.88

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prothrombin
CHEMBL204
 Ki 8.92 8.8025 1.2 4
Prothrombin
CHEMBL204
 Kd 8.88 8.88 1.3 1
Unchecked
CHEMBL612545
 Ki 8.7 8.7 2.0 1
Prothrombin
CHEMBL204
 IC50 8.4 7.0467 4.0 9
Trypsin
CHEMBL2095204
 Ki 8.37 8.37 4.3 1
Unchecked
CHEMBL612545
 IC50 8.1 7.7 8.0 2
Serine protease 1
CHEMBL3769
 IC50 7.95 7.95 11.2 1
Trypsin
CHEMBL2095204
 IC50 7.92 7.92 11.9 1
Plasma
CHEMBL613424
 EC50 6.4 6.4 400.0 1
Plasminogen
CHEMBL1801
 Ki 6.16 5.955 700.0 2
Tissue-type plasminogen activator
CHEMBL1873
 Ki 6.05 5.935 900.0 2
Vitamin K-dependent protein C
CHEMBL4444
 IC50 5.89 5.89 1300.0 1
Plasminogen
CHEMBL1801
 IC50 5.51 5.51 3060.0 1
Coagulation factor VII
CHEMBL3991
 IC50 5.48 5.48 3300.0 1
Coagulation factor X
CHEMBL244
 Ki 5.43 5.43 3680.0 1
Urokinase-type plasminogen activator
CHEMBL3286
 Ki 5.2 5.2 6300.0 1
Coagulation factor X
CHEMBL244
 IC50 4.82 4.7533 15200.0 3
Coagulation factor XI
CHEMBL2820
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 74.6 s Canis lupus familiaris
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 1.9 mL.min-1.kg-1 Homo sapiens
F 5.2 % Eutheria
F 24.0 % Canis lupus familiaris
F 3.0 % Homo sapiens
Fu 0.93 - Homo sapiens
Fu 0.93 - Homo sapiens
MRT 2.0 hr Homo sapiens
T1/2 1.6 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prothrombin Ki = 1.2 nM 8.92 Binding affinity against human thrombin 11909707
Prothrombin Ki = 1.3 nM 8.89 Inhibition of human thrombin 23899618
Prothrombin Kd = 1.31 nM 8.88 Binding affinity to thrombin (unknown origin) by surface plasmon resonance analy... 23899618
Prothrombin Ki = 2.0 nM 8.7 Inhibitory activity against thrombin. 12238922
Unchecked Ki = 2.0 nM 8.7 Binding affinity against Thrombin. 10669559
Prothrombin Ki = 2.0 nM 8.7 Inhibition of thrombin (unknown origin) 31658420
Prothrombin IC50 = 4.0 nM 8.4 Inhibition of human thrombin using S-2366 as substrate preincubated for 300 seco... 24418773
Trypsin Ki = 4.3 nM 8.37 Inhibition of human trypsin 23899618
Unchecked IC50 = 8.0 nM 8.1 Inhibition of human alpha thrombin by surface plasmon resonance assay 19371038
Serine protease 1 IC50 = 11.2 nM 7.95 In vitro inhibitory activity against trypsin 12781189
Trypsin IC50 = 11.9 nM 7.92 Inhibition of trypsin 16517159
Unchecked IC50 = 50.0 nM 7.3 Inhibition of bovine trypsin using S-2765 as chromogenic substrate preincubated ... 36462436
Prothrombin IC50 = 69.2 nM 7.16 Inhibition of thrombin 16517159
Prothrombin IC50 = 69.2 nM 7.16 Inhibition of thrombin by chromogenic assay 16460939
Prothrombin IC50 = 69.2 nM 7.16 In vitro inhibitory activity against thrombin 12781189
Prothrombin IC50 = 74.0 nM 7.13 Inhibition of free thrombin (unknown origin) using S2238 as substrate 23899618
Prothrombin IC50 = 85.2 nM 7.07 Inhibition of plasma clot-bound thrombin (unknown origin) using S2238 as substra... 23899618
Prothrombin IC50 = 90.0 nM 7.05 Inhibition of human thrombin using S-2238 as chromogenic substrate preincubated ... 36462436
Prothrombin IC50 = 110.0 nM 6.96 Inhibition of thrombin (unknown origin) assessed as fibrin clot formation 23899618
Plasma EC50 = 400.0 nM 6.4 Anticoagulant activity in human platelet-poor plasma assessed as endogenous thro... 36462436

Literature References

PubMed DOI Target Context # Activities
23899618 10.1016/j.bmcl.2013.07.008 Rattus norvegicus 23
20070106 10.1021/jm901371v Homo sapiens 8
23899618 10.1016/j.bmcl.2013.07.008 Prothrombin 6
18426954 10.1124/dmd.108.020479 ADMET 4
23899618 10.1016/j.bmcl.2013.07.008 Unchecked 4
19445515 10.1021/jm900403j Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
16460939 10.1016/j.bmcl.2006.01.046 Canis familiaris 2
36462436 10.1016/j.ejmech.2022.114855 Plasma 2
16517159 10.1016/j.bmcl.2006.02.040 Rattus norvegicus 2
23899618 10.1016/j.bmcl.2013.07.008 Plasma 2
16460939 10.1016/j.bmcl.2006.01.046 Rattus norvegicus 2
16517159 10.1016/j.bmcl.2006.02.040 Trypsin 1
16517159 10.1016/j.bmcl.2006.02.040 Coagulation factor X 1
16517159 10.1016/j.bmcl.2006.02.040 Plasminogen 1
16517159 10.1016/j.bmcl.2006.02.040 Tissue-type plasminogen activator 1
12781189 10.1016/s0960-894x(03)00347-0 Serine protease 1 1
12781189 10.1016/s0960-894x(03)00347-0 Prothrombin 1
10669559 10.1021/jm990412m Unchecked 1
12238922 10.1021/jm011110z ADMET 1

Data from ChEMBL 36 via Core Engine