A prodrug of melagatran, a thrombin inhibitor
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Active Metabolite(s)
9002300Melagatran
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Ximelagatran

Item No. 16862

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1R)-1-cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]-glycine, ethyl ester
CAS Number
192939-46-1
Synonyms
  • Exanta
  • H 376/95
Molecular Formula
C24H35N5O5
Formula Weight
473.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 5 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 1 mg/ml
λmax
265 nm
SMILES
N=C(NO)C1=CC=C(CNC([C@@H]2CCN2C([C@@H](C3CCCCC3)NCC(OCC)=O)=O)=O)C=C1
InChi Code
InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1
InChi Key
ZXIBCJHYVWYIKI-PZJWPPBQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    Product Description

    Ximelagatran is an ester prodrug of melagatran, a potent, direct, and reversible thrombin inhibitor (Ki = 1.2 nM).1,2 While melagatran has poor oral bioavailability, ximelagatran displays good bioavailability resulting, in part, from rapid absorption at the gastrointestinal tract, as well as rapid onset of action.2 Ximelagatran is converted to melagatran by reduction and hydrolysis at the liver and other tissues.1,2 It is used as an anticoagulant in a variety of situations, including thromboembolic disorders, stroke prevention in atrial fibrillation, and therapy in vein thrombosis.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Clement, B., and Lopian, K. Characterization of in vitro biotransformation of new, orally active, direct thrombin inhibitor ximelagatran, an amidoxime and ester prodrug. Drug Metab. Dispos. 31(5), 645-651 (2003).

    2. Ho, S.J., and Brighton, T.A. Ximelagatran: Direct thrombin inhibitor. Vasc. Health Risk Manag. 2(1), 49-58 (2006).

    3. Ufer, M. Comparative pharmacokinetics of vitamin K antagonists warfarin, phenprocoumon and acenocoumarol. Clin. Pharmacokinet. 44(12), 1227-1246 (2005).