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Merck

SML1768

Sigma-Aldrich

Ximelagatran

≥98% (HPLC)

Sinónimos:

H 376/95, N-[(1R)-1-Cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]-glycine ethyl ester

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About This Item

Fórmula empírica (notación de Hill):
C24H35N5O5
Número de CAS:
Peso molecular:
473.57
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

N/C(C1=CC=C(CNC([C@@H]2CCN2C([C@@H](C3CCCCC3)NCC(OCC)=O)=O)=O)C=C1)=N/O

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

Biochem/physiol Actions

It inhibits both clot-bound and free thrombin. It is quickly absorbed by the small intestine and converted to its active dipeptide drug form, Melagatran. Melagatran associates with the arginine side pocket in thrombin and inactivates it. Ximelagatran has a half-life of 4-5 hours. It is administered orally twice a day.
Ximelagatran is orally active, selective and potent direct thrombin inhibitor. Ximelagatran is a prodrug of thrombin inhibitor melagatran.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Stefan Russmann et al.
Hepatology (Baltimore, Md.), 52(2), 748-761 (2010-07-08)
Recent progress in research on drug-induced liver injury (DILI) has been determined by key developments in two areas. First, new technologies allow the identification of genetic risk factors with improved sensitivity, specificity, and efficiency. Second, new mechanistic concepts of DILI
Erik Sjögren et al.
Pharmaceutical research, 27(4), 597-607 (2010-02-09)
The double prodrug, ximelagatran, is bioconverted, via the intermediates ethylmelagatran and N-hydroxymelagatran, to the direct thrombin inhibitor, melagatran. The primary aim of this study was to investigate the hepatic metabolism and disposition of ximelagatran and the intermediates in pig. A
Dukes M N G.
Side Effects of Drugs Annual: A world-wide yearly survey of new data and trends in adverse drug reactions. (1977)
John J B
The Vein Book (2007)
Ximelagatran (Exanta): alternative to warfarin?
Vaughan C.
Proceedings (Baylor University. Medical Center), 18(1), 76- 80 (2005)

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