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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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.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 3:80,529,468...80,542,993
Ensembl chr 3:80,529,428...80,543,031
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Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19785
    role 19732
      application 19391
        pro-agent 8829
          prodrug 8609
            ximelagatran 1
Path 2
Term Annotations click to browse term
  CHEBI ontology 19785
    subatomic particle 19782
      composite particle 19782
        hadron 19782
          baryon 19782
            nucleon 19782
              atomic nucleus 19782
                atom 19782
                  main group element atom 19670
                    p-block element atom 19670
                      carbon group element atom 19572
                        carbon atom 19561
                          organic molecular entity 19561
                            organic group 18493
                              organic divalent group 18486
                                organodiyl group 18486
                                  carbonyl group 18389
                                    carbonyl compound 18389
                                      carboxylic acid 18060
                                        carboacyl group 17346
                                          univalent carboacyl group 17346
                                            carbamoyl group 17132
                                              carboxamide 17132
                                                dicarboxylic acid amide 3107
                                                  dicarboxylic acid monoamide 673
                                                    melagatran 1
                                                      ximelagatran 1
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