For research use only. Not for therapeutic Use.
Ximelagatran (Exanta or Exarta, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin[1] that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, this drug was discontinued due to hepatotoxicity (liver damage). Ximelagatran, a direct thrombin inhibitor,[3] was the first member of this class that can be taken orally. It acts solely by inhibiting the actions of thrombin. It is taken orally twice daily, and rapidly absorbed by the small intestine. Ximelagatran is a prodrug, being converted in vivo to the active agent melagatran.
| Catalog Number | R008237 |
| CAS Number | 192939-46-1 |
| Synonyms | N-[(1R)-1-Cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]glycine Ethyl Ester; Exanta; H 376/95; |
| Molecular Formula | C24H35N5O5 |
| Purity | ≥95% |
| Target | Thrombin |
| Solubility | Soluble in DMSO |
| Storage | Store at -20°C |
| InChI | InChI=1S/C24H35N5O5/c1-2-34-21(30)16-25-22(19-6-4-3-5-7-19)24(32)29-13-12-20(29)23(31)26-14-17-8-10-18(11-9-17)15-27-28-33/h8-11,15,19-20,22,25,28,33H,2-7,12-14,16H2,1H3,(H,26,31)/b27-15+/t20-,22+/m0/s1 |
| InChIKey | ZXIBCJHYVWYIKI-PZJWPPBQSA-N |
| SMILES | N=C(NO)C1=CC=C(CNC([C@@H]2CCN2C([C@@H](C3CCCCC3)NCC(OCC)=O)=O)=O)C=C1 |
| Reference | </br>1:In Silico and In Vitro Analysis of Interaction between Ximelagatran and Human Leukocyte Antigen (HLA)-DRB1*07:01. Hirasawa M, Hagihara K, Abe K, Ando O, Hirayama N.Int J Mol Sci. 2017 Mar 24;18(4). pii: E694. doi: 10.3390/ijms18040694. PMID: 28338626 Free PMC Article</br>2:Expression and Function of mARC: Roles in Lipogenesis and Metabolic Activation of Ximelagatran. Neve EP, Köfeler H, Hendriks DF, Nordling Å, Gogvadze V, Mkrtchian S, Näslund E, Ingelman-Sundberg M.PLoS One. 2015 Sep 17;10(9):e0138487. doi: 10.1371/journal.pone.0138487. eCollection 2015. PMID: 26378779 Free PMC Article</br>3:Predicting potential liver toxicity from phase 2 data: a case study with ximelagatran. Southworth H.Stat Med. 2014 Jul 30;33(17):2914-23. doi: 10.1002/sim.6142. Epub 2014 Mar 12. PMID: 24623062 </br>4:Synthesis of ximelagatran, melagatran, hydroxymelagatran, and ethylmelagatran in H-3 labeled form. Simonsson R, Stenhagen G, Ericsson C, Elmore CS.J Labelled Comp Radiopharm. 2013 May 30;56(6):334-7. doi: 10.1002/jlcr.3028. Epub 2013 Feb 16. PMID: 24285415 </br>5:Two-year carcinogenicity studies with the oral direct thrombin inhibitor ximelagatran in the rat and the mouse. Stong DB, Carlsson SC, Bjurström S, Fransson-Steen R, Healing G, Skånberg I.Int J Toxicol. 2012 Jul-Aug;31(4):348-57. doi: 10.1177/1091581812448881. Epub 2012 Jun 12. PMID: 22692977 </br>6:Effect on perfusion chamber thrombus size in patients with atrial fibrillation during anticoagulant treatment with oral direct thrombin inhibitors, AZD0837 or ximelagatran, or with vitamin K antagonists. Wolzt M, Eriksson UG, Gouya G, Leuchten N, Kapiotis S, Elg M, Schützer KM, Zetterstrand S, Holmberg M, Wåhlander K.Thromb Res. 2012 Apr;129(4):e83-91. doi: 10.1016/j.thromres.2011.08.018. Epub 2011 Sep 16. PMID: 21925716 </br>7:Comparison of a direct Factor Xa inhibitor, edoxaban, with dalteparin and ximelagatran: a randomised controlled trial in healthy elderly adults. Samama MM, Kunitada S, Oursin A, Depasse F, Heptinstall S.Thromb Res. 2010 Oct;126(4):e286-93. doi: 10.1016/j.thromres.2010.07.015. PMID: 20807664 </br>8:Differential effects of TAK-442, a novel orally active direct factor Xa inhibitor, and ximelagatran, a thrombin inhibitor, on factor V-mediated feedback on coagulation cascade and bleeding. Konishi N, Hiroe K, Kawamura M.Thromb Haemost. 2010 Sep;104(3):504-13. doi: 10.1160/TH09-12-0817. Epub 2010 Jul 20. PMID: 20664909 </br>9:Biliary excretion of ximelagatran and its metabolites and the influence of erythromycin following intraintestinal administration to healthy volunteers. Matsson EM, Eriksson UG, Knutson L, Hoffmann KJ, Logren U, Fridblom P, Petri N, Lennernäs H.J Clin Pharmacol. 2011 May;51(5):770-83. doi: 10.1177/0091270010370975. Epub 2010 Jul 27. PMID: 20663994 </br>10:Hepatic disposition of ximelagatran and its metabolites in pig; prediction of the impact of membrane transporters through a simple disposition model. Sjögren E, Bredberg U, Allard E, Arvidsson B, Bergquist J, Andersson TB, Lennernäs H.Pharm Res. 2010 Apr;27(4):597-607. doi: 10.1007/s11095-009-0016-y. Epub 2010 Feb 6. PMID: 20140637 |
