Melagatran

Summary

Melagatran (CHEMBL266349) is an approved small-molecule anticoagulant (ATC B01AE04) targeting F2; indicated across 1 condition including thrombotic disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AE04
• Targets: 1 (F2)
• Indications: 1 condition
• Chemistry: 429.5 Da · C22H31N5O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL266349
Name	Melagatran
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	183797
ChEBI	CHEBI:43966
ATC	B01AE04
Molecular formula	C22H31N5O4
Molecular weight	429.5
InChIKey	DKWNMCUOEDMMIN-PKOBYXMFSA-N

SMILES: C1CCC(CC1)[C@H](C(=O)N2CC[C@H]2C(=O)NCC3=CC=C(C=C3)C(=N)N)NCC(=O)O

IUPAC name: 2-[[(1R)-2-[(2S)-2-[(4-carbamimidoylphenyl)methylcarbamoyl]azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino]acetic acid

ChEBI definition: A member of the class of azetidines that is (2S)-azetidine 2-carboxylic acid in which the carboxylic acid has been converted to the amide corresponding to formal condensation with 4-(aminomethyl)benzenecarboximidamide and in which the hydrogen attached to the azetidine nitrogen is replaced by a (2R)-2-cyclohexyl-2-[(carboxymethyl)amino]acetyl group.

Pharmacological roles (ChEBI): anticoagulant, EC 3.4.21.5 (thrombin) inhibitor, serine protease inhibitor.

Also known as: Melagatran, melagatran, MELAGATRAN

Patent coverage: 1,272 distinct patent families (5,421 SureChEMBL compound mentions), from 1 matched compound structure(s). 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	Inhibition	8.7	1.4%	P00734

Broader ChEMBL bioactivity targets: 10 (assay-derived). Sample: Plasminogen, Tissue-type plasminogen activator, Prothrombin, Trypsin, Coagulation factor X, Coagulation factor XI, Urokinase-type plasminogen activator, Serine protease 1, Coagulation factor VII, Vitamin K-dependent protein C.

Bioactivity

ChEMBL activities: 26 potent at pChembl ≥ 5 of 30 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
F2	8.92	Ki	1.2	nM	CHEMBL_ACT_1232095
F2	8.89	Ki	1.3	nM	CHEMBL_ACT_13414447
F2	8.88	Kd	1.31	nM	CHEMBL_ACT_13414420
F2	8.7	Ki	2	nM	CHEMBL_ACT_19054656
F2	8.7	Ki	2	nM	CHEMBL_ACT_384483
F2	8.4	IC50	4	nM	CHEMBL_ACT_13914456
PRSS1	8.37	Ki	4.3	nM	CHEMBL_ACT_13414441
P00760	7.95	IC50	11.2	nM	CHEMBL_ACT_718206
PRSS1	7.92	IC50	11.9	nM	CHEMBL_ACT_1716720
F2	7.16	IC50	69.2	nM	CHEMBL_ACT_1716692
F2	7.16	IC50	69.2	nM	CHEMBL_ACT_1717480
F2	7.16	IC50	69.2	nM	CHEMBL_ACT_718205
F2	7.13	IC50	74	nM	CHEMBL_ACT_13414414
F2	7.07	IC50	85.2	nM	CHEMBL_ACT_13414411
F2	7.05	IC50	90	nM	CHEMBL_ACT_25587779
F2	6.96	IC50	110	nM	CHEMBL_ACT_13414417
PLG	6.16	Ki	700	nM	CHEMBL_ACT_19054715
PLAT	6.05	Ki	900	nM	CHEMBL_ACT_19054716
PROC	5.89	IC50	1300	nM	CHEMBL_ACT_13915067
PLAT	5.82	Ki	1510	nM	CHEMBL_ACT_13414437
PLG	5.75	Ki	1800	nM	CHEMBL_ACT_13414439
PLG	5.51	IC50	3060	nM	CHEMBL_ACT_1716732
F7	5.48	IC50	3300	nM	CHEMBL_ACT_13914411
F10	5.43	Ki	3680	nM	CHEMBL_ACT_13414446
F2	5.33	IC50	4700	nM	CHEMBL_ACT_70187
PLAU	5.2	Ki	6300	nM	CHEMBL_ACT_19054717

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

1 indication (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

Clinical trials

Total trials: 0.

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
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
XIMELAGATRAN	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