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Ximelagatran

CAT: 0024-sc-208491ASize: 5 mgDry Ice: NoHazardous: No
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CAT#:0024-sc-208491ASize:5 mg
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CAS Number
192939-46-1

Chemical Information

Ximelagatran

Ximelagatran is a member of the class of azetidines that is melagatran in which the carboxylic acid group has been converted to the corresponding ethyl ester and in which the amidine group has been converted into the corresponding amidoxime. A prodrug for melagatran, ximelagatran was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage. It has a role as an anticoagulant, a prodrug, a serine protease inhibitor and an EC 3.4.21.5 (thrombin) inhibitor. It is a secondary carboxamide, a tertiary carboxamide, an ethyl ester, a carboxamide, a member of azetidines, a secondary amino compound and an amidoxime. It is functionally related to a melagatran. It is a tautomer of a ximelagatran (hydroxylamine form).

CAS Number192939-46-1
PubChem CID9574101
IUPAC Nameethyl 2-[[(1R)-1-cyclohexyl-2-[(2S)-2-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methylcarbamoyl]azetidin-1-yl]-2-oxoethyl]amino]acetate
Molecular FormulaC24H35N5O5
Molecular Weight473.6
XLogP2.2
Topological Polar Surface Area146
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count11
Heavy Atom Count34
Formal Charge0
Complexity731
SMILES
CCOC(=O)CN[C@H](C1CCCCC1)C(=O)N2CC[C@H]2C(=O)NCC3=CC=C(C=C3)/C(=N/O)/N
InChI
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
InChIKey
ZXIBCJHYVWYIKI-PZJWPPBQSA-N
Chemical Structure
2D Structure
2D structure of Ximelagatran
CAS: 192939-46-1
CID: 9574101
Formula: C24H35N5O5
MW: 473.6
Interactive 3D Structure
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View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight473.6
XLogP32.2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count11
Exact Mass473.26381923
Monoisotopic Mass473.26381923
Topological Polar Surface Area146 Ų
Heavy Atom Count34
Formal Charge0
Complexity731
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA8363-5Ximelagatran
MBS6097709-01Ximelagatran Nitrile

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