Preferred Name |
ximelagatran |
|
Synonyms |
ximelagatran (oxime form) ximelagatranum H 376-95 Exanta H 376/95 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate Exarta ximelagatran H 37695 ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate |
|
Definitions |
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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage. |
|
ID |
http://purl.obolibrary.org/obo/CHEBI_65172 |
|
charge |
0 |
|
database_cross_reference |
PMID:17319469 PMID:16084146 DrugBank:DB04898 PMID:28338626 PMID:16106594 PMID:17636192 PMID:19028773 PMID:16123912 PMID:16511607 CAS:192939-46-1 KEGG:D01981 PMID:15487959 Reaxys:14559655 Drug_Central:2852 PMID:16767816 PMID:20020269 Wikipedia:Ximelagatran PMID:12846595 |
|
definition |
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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage. |
|
formula |
C24H35N5O5 |
|
has functional parent | ||
has role |
http://purl.obolibrary.org/obo/CHEBI_50249 http://purl.obolibrary.org/obo/CHEBI_65232 |
|
has_exact_synonym |
ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate |
|
has_obo_namespace |
chebi_ontology |
|
has_related_synonym |
ximelagatran (oxime form) ximelagatranum H 376-95 Exanta H 376/95 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate Exarta ximelagatran H 37695 |
|
id |
CHEBI:65172 |
|
in_subset | ||
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 |
|
is tautomer of | ||
label |
ximelagatran |
|
mass |
473.56520 |
|
monoisotopicmass |
473.26382 |
|
notation |
CHEBI:65172 |
|
prefLabel |
ximelagatran |
|
smiles |
[H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO |
|
treeView |
http://purl.obolibrary.org/obo/CHEBI_65234 http://purl.obolibrary.org/obo/CHEBI_50995 http://purl.obolibrary.org/obo/CHEBI_140326 http://purl.obolibrary.org/obo/CHEBI_140325 http://purl.obolibrary.org/obo/CHEBI_23990 |
|
subClassOf |
http://purl.obolibrary.org/obo/CHEBI_65234 http://purl.obolibrary.org/obo/CHEBI_50995 http://purl.obolibrary.org/obo/CHEBI_140326 http://purl.obolibrary.org/obo/CHEBI_140325 http://purl.obolibrary.org/obo/CHEBI_23990 |