loading...| Preferred Name |
ximelagatran |
| Synonyms |
ximelagatran H 376/95 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate H 376-95 ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate ximelagatranum Exarta H 37695 Exanta ximelagatran (oxime form) |
| 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.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 |
DrugBank:DB04898 PMID:16084146 PMID:12846595 PMID:28338626 PMID:16106594 CAS:192939-46-1 Reaxys:14559655 PMID:17319469 Wikipedia:Ximelagatran PMID:15487959 PMID:19028773 Drug_Central:2852 PMID:20020269 PMID:16123912 KEGG:D01981 PMID:16767816 PMID:17636192 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.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 functional parent | |
| has role |
http://purl.obolibrary.org/obo/CHEBI_50266 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 H 376/95 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate H 376-95 ximelagatranum Exarta H 37695 Exanta ximelagatran (oxime form) |
| 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_23990 http://purl.obolibrary.org/obo/CHEBI_140326 http://purl.obolibrary.org/obo/CHEBI_50995 http://purl.obolibrary.org/obo/CHEBI_37622 http://purl.obolibrary.org/obo/CHEBI_38777 |
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_23990 http://purl.obolibrary.org/obo/CHEBI_140326 http://purl.obolibrary.org/obo/CHEBI_50995 http://purl.obolibrary.org/obo/CHEBI_37622 http://purl.obolibrary.org/obo/CHEBI_38777 |