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The Drug-Drug Interactions Ontology
Last uploaded:
February 11, 2016
| Id | http://purl.obolibrary.org/obo/CHEBI_65172
http://purl.obolibrary.org/obo/CHEBI_65172
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|---|---|
| Preferred Name | ximelagatran |
| Synonyms |
ximelagatranum
C24H35N5O5
H 376-95
Exanta
ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate
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
ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate
H 37695
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| Type | http://www.w3.org/2002/07/owl#Class |
All Properties
| prefLabel | ximelagatran
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|---|---|
| label | ximelagatran
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| DBSynonym | h 376/95
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| ATCCode | B01AE05
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| 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 to 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.
Ximelagatran (Exanta? or Exarta?, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, its manufacturer AstraZeneca announced that it would not attempt to market ximelagatran after reports of hepatotoxicity (liver damage) during trials, and to discontinue its distribution in countries where the drug had been approved.
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| has pharmacological target | |
| inhibits | |
| type | |
| has role | |
| InChIKey | InChIKey=ZXIBCJHYVWYIKI-PZJWPPBQSA-N
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| is metabolised by | |
| Synonym | ximelagatranum
C24H35N5O5
H 376-95
Exanta
ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate
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
ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate
H 37695
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| xref |
SUBMITTER:D01981
CiteXplore:12846595
CASRN:192939-46-1
CiteXplore:16084146
CiteXplore:19028773
PubChem Substance:46509040
ChemSpider:7848559
CiteXplore:16511607
CiteXplore:17636192
CiteXplore:20020269
CiteXplore:17319469
Reaxys:14559655
CiteXplore:16123912
PharmGKB:PA161748474
SUBMITTER:DB04898
Wikipedia:http://en.wikipedia.org/wiki/Ximelagatran
CiteXplore:16106594
PubChem Compound:9574101
CiteXplore:15487959
Wikipedia:Ximelagatran
ChEMBL:578003
CiteXplore:16767816
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| CASRN | 192939-46-1
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| prefixIRI | obo2:CHEBI_65172
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| SMILES |
[H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO
CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1
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| 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
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| DBBrand |
exarta
exanta
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| subClassOf |
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