Ximelagatran

Summary

Ximelagatran (CHEMBL522038) is an approved small molecule (ATC B01AE05) targeting F2; indicated across 3 conditions including thrombotic disease and atrial fibrillation.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AE05
• Targets: 1 (F2)
• Indications: 3 conditions
• Clinical trials: 2
• Chemistry: 473.6 Da · C24H35N5O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL522038
Name	Ximelagatran
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	5478933
ChEBI	CHEBI:136702
ATC	B01AE05
Molecular formula	C24H35N5O5
Molecular weight	473.6
InChIKey	ZXIBCJHYVWYIKI-PZJWPPBQSA-N

SMILES: CCOC(=O)CN[C@H](C1CCCCC1)C(=O)N2CC[C@H]2C(=O)NCC3=CC=C(C=C3)/C(=N\O)/N

IUPAC name: ethyl 2-[[(1R)-1-cyclohexyl-2-[(2S)-2-[[4-[(E)-N’-hydroxycarbamimidoyl]phenyl]methylcarbamoyl]azetidin-1-yl]-2-oxoethyl]amino]acetate

ChEBI definition: A member of the class of azetidines that is melagatran in which the carboxylic acid group has been converted into the corresponding ethyl ester and in which the amidine group has been converted to the corresponding hydroxylamine. Tautomeric with the oxime form of ximelagatran.

Also known as: Exanta, H 376/95, H-376/95, Ximelagatran, ximelagatran, XIMELAGATRAN, SID144207182

Patent coverage: 1,647 distinct patent families (7,429 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 7,374 (99%) 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			1.4%	P00734

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Prothrombin.

Bioactivity

ChEMBL activities: 2 potent at pChembl ≥ 5 of 2 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
F2	8.7	Ki	2.01	nM	CHEMBL_ACT_18916473
F2	6.5	AC50	320	nM	CHEMBL_ACT_25197154

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

3 indications (1 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
atrial fibrillation	2	MONDO:0004981	EFO:0000275

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

Clinical trials

Total trials: 2.

Phase distribution

Phase	Trials
PHASE3	1
PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00206089	PHASE3	TERMINATED	Melagatran/Ximelagatran Versus Enoxaparin for the Prevention of Venous Thromboembolic Events
NCT00206063	PHASE2	TERMINATED	Long Term Open Follow-up With H376/95 vs. Warfarin

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
ARGATROBAN	ChEMBL	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
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