CHEBI:65172 - ximelagatran

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ChEBI Name ximelagatran
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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Rebecca Foulger
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Formula C24H35N5O5
Net Charge 0
Average Mass 473.56520
Monoisotopic Mass 473.26382
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
SMILES [H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): serine protease inhibitor
Any protease inhibitor that restricts the action of a serine protease.
EC (thrombin) inhibitor
An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of thrombin (EC
Application(s): anticoagulant
An agent that prevents blood clotting.
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing ximelagatran (CHEBI:65172) has functional parent melagatran (CHEBI:43966)
ximelagatran (CHEBI:65172) has role anticoagulant (CHEBI:50249)
ximelagatran (CHEBI:65172) has role EC (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 ximelagatran (hydroxylamine form) (CHEBI:136702) is tautomer of ximelagatran (CHEBI:65172)
ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate
INNs Sources
ximelagatran WHO MedNet
ximélagatran WHO MedNet
ximelagatrán WHO MedNet
ximelagatranum WHO MedNet
Synonyms Sources
ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate ChEBI
H 376-95 ChemIDplus
H 376/95 ChemIDplus
H 37695 ChemIDplus
ximelagatran (oxime form) ChEBI
Manual Xrefs Databases
2852 DrugCentral
DB04898 DrugBank
Ximelagatran Wikipedia
View more database links
Registry Numbers Types Sources
14559655 Reaxys Registry Number Reaxys
192939-46-1 CAS Registry Number ChemIDplus
192939-46-1 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
12846595 PubMed citation Europe PMC
15487959 PubMed citation Europe PMC
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16767816 PubMed citation Europe PMC
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Last Modified
07 March 2018