ximelagatran

Small moleculeexperimental

Ximelagatran is an anticoagulant that has been investigated extensively as a replacement for warfarin that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, its manufacturer AstraZeneca announced that it would withdraw pending applications for marketing approval after reports of hepatotoxicity during trials, and discontinue its distribution in countries where the drug had been approved. — Wikipedia

Clinical trial activity

2 trials · 1 clinical orgs · 0 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Aug 1, 1999 (NCT00206063)

Timeline

1990s

Jan 1, 1999
Earliest Phase 2 Sponsor(trial)

2000s

Jan 1, 2005
Earliest Phase 3 Sponsor(trial)

Indications

Studied for

Mechanism of action

ThrombinINHIBITOR
F2 inhibitor
Ximelagatran is a prodrug that undergoes rapid enzymatic conversion to the active compound melagatran. Melagatran is a potent, competitive, and reversible direct inhibitor binding to the active site of soluble and clot-bound ¿-thrombin. It inhibits coagulation.
Melagatran, the active molecule, binds to the arginine side pocket of thrombin.
- Prothrombin (F2) ↗

Chemistry & pharmacology

Loading structure…

SMILES

N=C(N)c1ccc(CNC(=O)[C@@H]2CCN2C(=O)[C@H](NCC(=O)O)C2CCCCC2)cc1

Mol. weight: 429.52 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Single Stereoisomer
Inorganic: No
Polymer: No
Delivery: Parenteral

Oral

Parenteral

Yes

Topical

Sources

Also known as

ethyl 2-[[(1r)-1-cyclohexyl-2- [(2s)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate
ethyl 2-[[(1r)-1-cyclohexyl-2- [(2s)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate
exanta
exanta
exanta
exanta
exanta (proposed)
exarta
exarta
glycine, n-((1)1-cyclohexyl-2-((2)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl ester
glycine, n-((1r)1-cyclohexyl-2-((2s)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl ester
h 37695
h 37695
h 376 95
h 376-95
h 376-95
h 376-95
h 376/95
h 376/95
h 376/95
h-376/95
h-376/95
h-376/95
h-376/95
h-376/95
ximelagatran
ximelagatran
ximelagatran
ximelagatran
ximelagatran
ximelagatran
ximelagatran
ximelagatran
xi-melagatran
ximelagatranum
ximelagatranum

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT00206089	Phase 3	Sep 1, 2005	AstraZeneca
NCT00206063	Phase 2	Aug 1, 1999	AstraZeneca

Showing 2 of 2 trials

Page 1 / 1

Organizations

Research & Development (1)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
AstraZeneca	For profit	2	2	2	1999

1 organizations

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