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SML1768

Sigma-Aldrich

Ximelagatran

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C24H35N5O5
CAS Number:
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
Ximelagatran (Exanta): alternative to warfarin?
Vaughan C.
Proceedings (Baylor University. Medical Center), 18(1), 76- 80 (2005)

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