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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:ximelagatran
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Accession:CHEBI:65172 term browser browse the term
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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.
Synonyms:exact_synonym: ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate
 related_synonym: Exanta;   Exarta;   Formula=C24H35N5O5;   H 376-95;   H 37695;   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;   SMILES=[H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO;   ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate;   ximelagatran (oxime form);   ximelagatranum
 xref: CAS:192939-46-1;   DrugBank:DB04898;   Drug_Central:2852;   KEGG:D01981
 xref_mesh: MESH:C426686
 xref: PMID:12846595;   PMID:15487959;   PMID:16084146;   PMID:16106594;   PMID:16123912;   PMID:16511607;   PMID:16767816;   PMID:17319469;   PMID:17636192;   PMID:19028773;   PMID:20020269;   PMID:28338626;   Reaxys:14559655;   Wikipedia:Ximelagatran
 cyclic_relationship: is_tautomer_of CHEBI:136702


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ximelagatran term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G F2 coagulation factor II decreases cleavage
multiple interactions
ISO ximelagatran results in decreased cleavage of F2 protein
ximelagatran binds to and results in decreased activity of F2 protein
CTD PMID:15155122 PMID:16084352 PMID:16194202 PMID:17314111 NCBI chr 3:77,596,196...77,609,486
Ensembl chr 3:77,596,198...77,609,486
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Path 1
Term Annotations click to browse term
  CHEBI ontology 19821
    role 19769
      application 19481
        pro-agent 10099
          prodrug 9902
            ximelagatran 1
Path 2
Term Annotations click to browse term
  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic group 18737
                              organic divalent group 18728
                                organodiyl group 18728
                                  carbonyl group 18675
                                    carbonyl compound 18675
                                      carboxylic acid 18373
                                        carboacyl group 17485
                                          univalent carboacyl group 17485
                                            carbamoyl group 17299
                                              carboxamide 17299
                                                dicarboxylic acid amide 3133
                                                  dicarboxylic acid monoamide 676
                                                    melagatran 1
                                                      ximelagatran 1
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