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Compound Detail

CHEMBL522038

XIMELAGATRAN
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(/C(N)=N\O)cc1)C1CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL522038
Name XIMELAGATRAN
Phase Approved
Structure Type MOL
InChI Key ZXIBCJHYVWYIKI-PZJWPPBQSA-N
Active Moiety CHEMBL266349

Known Names

Exanta H 376/95 H-376/95 Ximelagatran
1
Targets
1
Activities
1
Assay Types
8
PK Parameters
20
Publications
4
Known Names
3
Indications
1
Mechanisms

Molecular Properties

473.6
MW (Da)
1.10
ALogP
7
HBA
4
HBD
146.3
PSA (Ų)
0.13
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product Prodrug
USAN Stem -gatran
USAN Year 2002

Extended Properties

Molecular Formula C24H35N5O5
MW 473.57
Aromatic Rings 1
Heavy Atoms 34
NP-Likeness -0.82

Mechanism of Action

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

Indications

Thrombosis Thromboembolism Atrial Fibrillation

ATC Classification

B01AE05
ximelagatran
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Drug Warnings

Withdrawn
hepatotoxicity
severe liver injury during longer-term (more than 11 days) treatment
Country: Worldwide   Year: 2006
Withdrawn
hepatotoxicity
severe liver injury during longer-term (more than 11 days) treatment
Country: Worldwide   Year: 2006
Withdrawn
hepatotoxicity
serious liver injury
Country: Worldwide   Year: 2006
Withdrawn
hepatotoxicity
serious liver injury
Country: Worldwide   Year: 2006

Activity Summary

Ki 1 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prothrombin
CHEMBL204
 Ki 8.7 8.7 2.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 1000.0 nM Rattus norvegicus
Cmax 1100.0 nM Rattus norvegicus
F 19.0 % Homo sapiens
F 10.0 % Canis lupus familiaris
F 5.0 % Rattus norvegicus
F 20.0 % Homo sapiens
F 18.0 % Homo sapiens
F 20.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prothrombin Ki = 2.01 nM 8.7 Inhibition of thrombin (unknown origin) 31188592

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
19250826 10.1016/j.bmcl.2009.02.047 Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
23899618 10.1016/j.bmcl.2013.07.008 No relevant target 2
23899618 10.1016/j.bmcl.2013.07.008 Rattus norvegicus 1
23899618 10.1016/j.bmcl.2013.07.008 Canis familiaris 1
- 10.1039/C5MD00479A Homo sapiens 1
23899618 10.1016/j.bmcl.2013.07.008 Homo sapiens 1
29072911 10.1021/acs.jmedchem.7b00772 ADMET 1
29072911 10.1021/acs.jmedchem.7b00772 Homo sapiens 1
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 1
27347787 10.1021/acs.jmedchem.5b01871 ADMET 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
21624500 10.1016/j.drudis.2011.05.007 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine