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ximelagatran
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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage.

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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > enzyme inhibitor [CHEBI:23924] > protease inhibitor [CHEBI:37670] > serine protease inhibitor [CHEBI:64926]
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more general categories    information about this item
03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 enzyme inhibitor [CHEBI:23924] (825) 
 thrombin inhibitor [CHEBI:65232] (4) 
 ximelagatran [CHEBI:65172] (1)
 protease inhibitor [CHEBI:37670] (37) 
 serine protease inhibitor [CHEBI:64926] (3) 
 ximelagatran [CHEBI:65172] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 hematologic agent [CHEBI:50248] (64) 
 anticoagulant [CHEBI:50249] (29) 
 ximelagatran [CHEBI:65172] (1)
 prodrug [CHEBI:50266] (88) 
 ximelagatran [CHEBI:65172] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 amidine [CHEBI:2634] (21) 
 amidoxime [CHEBI:65234] (1) 
 ximelagatran [CHEBI:65172] (1)
 amide [CHEBI:32988] (1863) 
 primary amide [CHEBI:33256] (1586) 
 carboxamide [CHEBI:37622] (1381) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 carboxamide [CHEBI:37622] (1381) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organic amino compound [CHEBI:50047] (2472) 
 secondary amino compound [CHEBI:50995] (110) 
 ximelagatran [CHEBI:65172] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 ximelagatran [CHEBI:65172] (1)
 carboxamide [CHEBI:37622] (1381) 
 ximelagatran [CHEBI:65172] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 ximelagatran [CHEBI:65172] (1)
 carboxamide [CHEBI:37622] (1381) 
 ximelagatran [CHEBI:65172] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 carboxamide [CHEBI:37622] (1381) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organic amino compound [CHEBI:50047] (2472) 
 secondary amino compound [CHEBI:50995] (110) 
 ximelagatran [CHEBI:65172] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 ximelagatran [CHEBI:65172] (1)
 carboxamide [CHEBI:37622] (1381) 
 ximelagatran [CHEBI:65172] (1)
 ester [CHEBI:35701] (3370) 
 carboxylic ester [CHEBI:33308] (1495) 
 ximelagatran [CHEBI:65172] (1)
 organic amino compound [CHEBI:50047] (2472) 
 secondary amino compound [CHEBI:50995] (110) 
 ximelagatran [CHEBI:65172] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 ximelagatran [CHEBI:65172] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 monocyclic compound [CHEBI:33661] (2007) 
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 heteromonocyclic compound [CHEBI:33670] (2004) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organic heteromonocyclic compound [CHEBI:25693] (2004) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 azetidines [CHEBI:38777] (21) 
 ximelagatran [CHEBI:65172] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic ester [CHEBI:33308] (1495) 
 ximelagatran [CHEBI:65172] (1)
ChEBI Compound Accession Identifier:   [CHEBI:65172]
ChEBI Compound Description:   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.
ChEBI Compound Identification Number:   65172
ChEBI InChI Value:   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
ChEBI InChIKey Value:   ZXIBCJHYVWYIKI-PZJWPPBQSA-N
ChEBI Compound Name:   ximelagatran
ChEBI SMILES Value:   [H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO
ChEBI Substance ID:   160645186
ChEBI URL:   ChEBI:65172
ChemSpider ID:   7848559
Ontomatica Chemical Accession Key (OnChAKey):   ZXIBCJHYVWYIKI_PZJWPPBQSA_N_000_000000
PubChem Compound ID:   9574101