loading...| Preferred Name |
ximelagatran |
|
| Synonyms |
ximelagatran ximelagatranum ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate ximelagatran (oxime form) Exanta Exarta H 376-95 H 376/95 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.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 |
|
| alternative term |
ximelagatran ximelagatranum ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate ximelagatran (oxime form) Exanta Exarta H 376-95 H 376/95 H 37695 ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate |
|
| bearer of |
http://purl.obolibrary.org/obo/CHEBI_50249 http://purl.obolibrary.org/obo/CHEBI_65232 |
|
| charge |
0 |
|
| database_cross_reference |
KEGG:D01981 Reaxys:14559655 PMID:20020269 PMID:15487959 Drug_Central:2852 PMID:16084146 PMID:12846595 PMID:17636192 PMID:16106594 PMID:19028773 Wikipedia:Ximelagatran PMID:16767816 CAS:192939-46-1 PMID:16123912 PMID:28338626 DrugBank:DB04898 PMID:17319469 PMID:16511607 |
|
| 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.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_exact_synonym |
ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate |
|
| has_functional_parent | ||
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
ximelagatran ximelagatranum ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate ximelagatran (oxime form) Exanta Exarta H 376-95 H 376/95 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 |
|
| RO_0000087 |
http://purl.obolibrary.org/obo/CHEBI_50249 http://purl.obolibrary.org/obo/CHEBI_65232 |
|
| smiles |
[H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO |
|
| 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 |