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CHEBI:65172 - ximelagatran

ChEBI IDCHEBI:65172
ChEBI Nameximelagatran
Stars
DefinitionA 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.
Last Modified7 March 2018
SubmitterRebecca Foulger
DownloadsMolfile
FormulaC24H35N5O5
Net Charge0
Average Mass473.574
Monoisotopic Mass473.26382
SMILES[H][C@@]1(C(=O)NCc2ccc(C(N)=NO)cc2)CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1
InChIInChI=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
InChIKeyZXIBCJHYVWYIKI-PZJWPPBQSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
serine protease inhibitor  Any protease inhibitor that restricts the action of a serine protease.
EC 3.4.21.5 (thrombin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of thrombin (EC 3.4.21.5).
Applications:
anticoagulant  An agent that prevents blood clotting.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
ximelagatran (CHEBI:65172) has functional parent melagatran (CHEBI:43966)
ximelagatran (CHEBI:65172) has role anticoagulant (CHEBI:50249)
ximelagatran (CHEBI:65172) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
ximelagatran (CHEBI:65172) has role prodrug (CHEBI:50266)
ximelagatran (CHEBI:65172) has role serine protease inhibitor (CHEBI:64926)
ximelagatran (CHEBI:65172) is a amidoxime (CHEBI:65234)
ximelagatran (CHEBI:65172) is a azetidines (CHEBI:38777)
ximelagatran (CHEBI:65172) is a carboxamide (CHEBI:37622)
ximelagatran (CHEBI:65172) is a ethyl ester (CHEBI:23990)
ximelagatran (CHEBI:65172) is a secondary amino compound (CHEBI:50995)
ximelagatran (CHEBI:65172) is a secondary carboxamide (CHEBI:140325)
ximelagatran (CHEBI:65172) is a tertiary carboxamide (CHEBI:140326)
ximelagatran (CHEBI:65172) is tautomer of ximelagatran (hydroxylamine form) (CHEBI:136702)
Incoming Relation(s)
ximelagatran (hydroxylamine form) (CHEBI:136702) is tautomer of ximelagatran (CHEBI:65172)
IUPAC Name 
ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate
INNs  Source
ximélagatranWHO MedNet
ximelagatránWHO MedNet
ximelagatranWHO MedNet
ximelagatranumWHO MedNet
Synonyms  Source
ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetateChEBI
ExantaSUBMITTER
ExartaSUBMITTER
H 376-95ChemIDplus
H 376/95ChemIDplus
H 37695ChemIDplus
Manual XrefsDatabases
D01981KEGG DRUG
DB04898DrugBank
XimelagatranWikipedia
2852DrugCentral
Registry NumbersSources
Reaxys:14559655Reaxys
CAS:192939-46-1ChemIDplus
CAS:192939-46-1KEGG DRUG
Citations