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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015603
Secondary Accession Numbers
  • HMDB15603
Metabolite Identification
Common NameXimelagatran
DescriptionXimelagatran, also known as exanta or H 376-95, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. There was also a numerically higher mortality against warfarin. Ximelagatran is a drug which is used for the treatment of acute deep vein thrombosis. Ximelagatran was expected to replace warfarin and sometimes aspirin and heparin in many therapeutic settings, including deep venous thrombosis, prevention of secondary venous thromboembolism and complications of atrial fibrillation such as stroke. Ximelagatran is a very strong basic compound (based on its pKa). In humans, ximelagatran is involved in ximelagatran action pathway. Subsequent analysis of Phase 2 clinical study data using extreme value modelling (see Extreme value theory) showed that the elevated liver enzyme levels observed in Phase 3 clinical studies could have been predicted; if this had been known at the time, it might have affected decisions on future development of the compound. The efficacy of ximelagatran for these indications had been well documented, except for non valvular atrial fibrillation. A disadvantage recognised early was the absence of an antidote in case acute bleeding develops, while warfarin can be antagonised by prothrombin complex concentrate and/or vitamin K and heparin by protamine sulfate. Ximelagatran, a direct thrombin inhibitor, was the first member of this class that can be taken orally. It is taken orally twice daily, and rapidly absorbed by the small intestine.
Structure
Data?1582753315
Synonyms
ValueSource
Ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetateChEBI
ExantaChEBI
ExartaChEBI
H 376-95ChEBI
H 376/95ChEBI
H 37695ChEBI
Ximelagatran (oxime form)ChEBI
XimelagatranumChEBI
Ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetic acidGenerator
XI-melagatranHMDB
Glycine, N-((1R)1-cyclohexyl-2-((2S)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl esterHMDB
Glycine, N-((1)1-cyclohexyl-2-((2)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl esterHMDB
Chemical FormulaC24H35N5O5
Average Molecular Weight473.5652
Monoisotopic Molecular Weight473.263819255
IUPAC Nameethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate
Traditional Nameximelagatran
CAS Registry Number192939-46-1
SMILES
CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1
InChI Identifier
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
InChI KeyZXIBCJHYVWYIKI-PZJWPPBQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid ester
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Amidoxime
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Amidine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.084 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP1.35ALOGPS
logP0.87ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.35 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity126.57 m³·mol⁻¹ChemAxon
Polarizability52.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+210.17531661259
DarkChem[M-H]-206.49931661259
DeepCCS[M+H]+217.01730932474
DeepCCS[M-H]-214.62230932474
DeepCCS[M-2H]-247.68330932474
DeepCCS[M+Na]+222.9330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XimelagatranCCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC13902.3Standard polar33892256
XimelagatranCCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC13718.1Standard non polar33892256
XimelagatranCCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC14162.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ximelagatran,1TMS,isomer #1CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC14145.6Semi standard non polar33892256
Ximelagatran,1TMS,isomer #1CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC13708.9Standard non polar33892256
Ximelagatran,1TMS,isomer #1CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC16234.4Standard polar33892256
Ximelagatran,1TMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C4030.1Semi standard non polar33892256
Ximelagatran,1TMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C3567.9Standard non polar33892256
Ximelagatran,1TMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C6625.6Standard polar33892256
Ximelagatran,1TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC13971.1Semi standard non polar33892256
Ximelagatran,1TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC13587.0Standard non polar33892256
Ximelagatran,1TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC16521.3Standard polar33892256
Ximelagatran,2TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C4043.1Semi standard non polar33892256
Ximelagatran,2TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C3632.1Standard non polar33892256
Ximelagatran,2TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C5875.9Standard polar33892256
Ximelagatran,2TMS,isomer #2CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC14006.0Semi standard non polar33892256
Ximelagatran,2TMS,isomer #2CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC13673.9Standard non polar33892256
Ximelagatran,2TMS,isomer #2CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC15737.4Standard polar33892256
Ximelagatran,2TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC14072.8Semi standard non polar33892256
Ximelagatran,2TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC13777.5Standard non polar33892256
Ximelagatran,2TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC15736.6Standard polar33892256
Ximelagatran,2TMS,isomer #4CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C3917.8Semi standard non polar33892256
Ximelagatran,2TMS,isomer #4CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C3544.6Standard non polar33892256
Ximelagatran,2TMS,isomer #4CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C6289.1Standard polar33892256
Ximelagatran,3TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C3958.9Semi standard non polar33892256
Ximelagatran,3TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C3627.3Standard non polar33892256
Ximelagatran,3TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C5356.6Standard polar33892256
Ximelagatran,3TMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C4006.9Semi standard non polar33892256
Ximelagatran,3TMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C3705.1Standard non polar33892256
Ximelagatran,3TMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C5361.4Standard polar33892256
Ximelagatran,3TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC13952.7Semi standard non polar33892256
Ximelagatran,3TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC13751.7Standard non polar33892256
Ximelagatran,3TMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC15236.8Standard polar33892256
Ximelagatran,4TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C3936.5Semi standard non polar33892256
Ximelagatran,4TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C3694.9Standard non polar33892256
Ximelagatran,4TMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C4910.1Standard polar33892256
Ximelagatran,1TBDMS,isomer #1CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC14343.6Semi standard non polar33892256
Ximelagatran,1TBDMS,isomer #1CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC13879.4Standard non polar33892256
Ximelagatran,1TBDMS,isomer #1CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC16112.3Standard polar33892256
Ximelagatran,1TBDMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C4288.7Semi standard non polar33892256
Ximelagatran,1TBDMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C3743.7Standard non polar33892256
Ximelagatran,1TBDMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C6578.7Standard polar33892256
Ximelagatran,1TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC14217.2Semi standard non polar33892256
Ximelagatran,1TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC13760.7Standard non polar33892256
Ximelagatran,1TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC16495.0Standard polar33892256
Ximelagatran,2TBDMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C4481.2Semi standard non polar33892256
Ximelagatran,2TBDMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C3969.5Standard non polar33892256
Ximelagatran,2TBDMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C5739.3Standard polar33892256
Ximelagatran,2TBDMS,isomer #2CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC14416.5Semi standard non polar33892256
Ximelagatran,2TBDMS,isomer #2CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC14010.7Standard non polar33892256
Ximelagatran,2TBDMS,isomer #2CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC15620.4Standard polar33892256
Ximelagatran,2TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC14500.3Semi standard non polar33892256
Ximelagatran,2TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC14085.8Standard non polar33892256
Ximelagatran,2TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC15590.7Standard polar33892256
Ximelagatran,2TBDMS,isomer #4CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C4387.0Semi standard non polar33892256
Ximelagatran,2TBDMS,isomer #4CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C3879.3Standard non polar33892256
Ximelagatran,2TBDMS,isomer #4CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C6218.6Standard polar33892256
Ximelagatran,3TBDMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C4565.0Semi standard non polar33892256
Ximelagatran,3TBDMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C4093.3Standard non polar33892256
Ximelagatran,3TBDMS,isomer #1CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C5342.5Standard polar33892256
Ximelagatran,3TBDMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C4628.3Semi standard non polar33892256
Ximelagatran,3TBDMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C4150.1Standard non polar33892256
Ximelagatran,3TBDMS,isomer #2CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C5286.1Standard polar33892256
Ximelagatran,3TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC14522.3Semi standard non polar33892256
Ximelagatran,3TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC14197.4Standard non polar33892256
Ximelagatran,3TBDMS,isomer #3CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC15192.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ximelagatran GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-4982400000-32fe628a565ad95d34f72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ximelagatran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 10V, Positive-QTOFsplash10-03ka-0910600000-44563426df349abe783a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 20V, Positive-QTOFsplash10-01ot-1900000000-993c6a2f4f07b4664b532016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 40V, Positive-QTOFsplash10-0002-2900000000-7463f581ac8e0bfad3632016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 10V, Negative-QTOFsplash10-010r-1091600000-caf9b25e0e59704abc3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 20V, Negative-QTOFsplash10-0i6r-1390100000-fa8587138131e92bfa4b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 40V, Negative-QTOFsplash10-0f6t-9780000000-e48b26348d984d96c2ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 10V, Positive-QTOFsplash10-00di-0011900000-d107c431444eff177ff32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 20V, Positive-QTOFsplash10-00dj-0242900000-d014519f397e125b9c122021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 40V, Positive-QTOFsplash10-07cs-2910000000-1bde1af9d5c933ea620b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 10V, Negative-QTOFsplash10-00di-0000900000-23339a41ce7aee4805942021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 20V, Negative-QTOFsplash10-00di-0209400000-b804ae6102407413420b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ximelagatran 40V, Negative-QTOFsplash10-0a4i-2691100000-8ca0829e1959417b49c42021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04898 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04898 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04898
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7848559
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXimelagatran
METLIN IDNot Available
PubChem Compound656635
PDB IDNot Available
ChEBI ID65172
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Eriksson H, Wahlander K, Gustafsson D, Welin LT, Frison L, Schulman S: A randomized, controlled, dose-guiding study of the oral direct thrombin inhibitor ximelagatran compared with standard therapy for the treatment of acute deep vein thrombosis: THRIVE I. J Thromb Haemost. 2003 Jan;1(1):41-7. [PubMed:12871538 ]
  2. Francis CW, Berkowitz SD, Comp PC, Lieberman JR, Ginsberg JS, Paiement G, Peters GR, Roth AW, McElhattan J, Colwell CW Jr: Comparison of ximelagatran with warfarin for the prevention of venous thromboembolism after total knee replacement. N Engl J Med. 2003 Oct 30;349(18):1703-12. [PubMed:14585938 ]
  3. Weitz JI: New anticoagulants for treatment of venous thromboembolism. Circulation. 2004 Aug 31;110(9 Suppl 1):I19-26. [PubMed:15339877 ]
  4. Bergqvist D, Solhaug JH, Holmdahl L, Eriksson UG, Andersson M, Boberg B, Ogren M: Pharmacokinetics, preliminary efficacy and safety of subcutaneous melagatran and oral ximelagatran : a multicentre study of thromboprophylaxis in elective abdominal surgery. Clin Drug Investig. 2004;24(3):127-36. [PubMed:17516699 ]
  5. Koscielny J, Kiesewetter H, Jorg I, Harenberg J: Ximelagatran for treatment and prophylaxis of recurrent events in deep vein thrombosis. Clin Appl Thromb Hemost. 2007 Jul;13(3):299-307. [PubMed:17636192 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]