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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:34 UTC
HMDB IDHMDB14447
Secondary Accession NumbersNone
Metabolite Identification
Common NameTranexamic Acid
DescriptionTranexamic Acid is only found in individuals that have used or taken this drug. It is an antifibrinolytic hemostatic used in severe hemorrhage. [PubChem]Tranexamic acid competitively inhibits activation of plasminogen (via binding to the kringle domain), thereby reducing conversion of plasminogen to plasmin (fibrinolysin), an enzyme that degrades fibrin clots, fibrinogen, and other plasma proteins, including the procoagulant factors V and VIII. Tranexamic acid also directly inhibits plasmin activity, but higher doses are required than are needed to reduce plasmin formation.
Structure
Thumb
Synonyms
ValueSource
Acide tranexamiqueChEBI
acido TranexamicoChEBI
Acidum tranexamicumChEBI
CyklokapronChEBI
TranexamsaeureChEBI
Tranexmic acidChEBI
Tranhexamic acidChEBI
trans AMCHAChEBI
trans-4-(Aminomethyl)cyclohexanecarboxylic acidChEBI
trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylIC ACIDChEBI
trans-AmchaChEBI
trans-Tranexamic acidChEBI
TranexamateGenerator
TranexmateGenerator
TranhexamateGenerator
trans-4-(Aminomethyl)cyclohexanecarboxylateGenerator
trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylateGenerator
trans-TranexamateGenerator
Chemical FormulaC8H15NO2
Average Molecular Weight157.2102
Monoisotopic Molecular Weight157.110278729
IUPAC Name(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid
Traditional Nametranexamic acid
CAS Registry Number1197-18-8
SMILES
NC[C@H]1CC[C@@H](CC1)C(O)=O
InChI Identifier
InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7-
InChI KeyInChIKey=GYDJEQRTZSCIOI-LJGSYFOKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Drug
Biofunction
  • Antifibrinolytic Agents
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.82e+01 g/LNot Available
LogP0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility18.2 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.6ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.9 m3·mol-1ChemAxon
Polarizability17.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tranexamic Acid PathwaySMP00287Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
UrineDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableUlcerative colitis details
UrineDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedUlcerative colitis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00302
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10482000
KEGG Compound IDC12535
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTranexamic_acid
NuGOwiki LinkHMDB14447
Metagene LinkHMDB14447
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDAMH
ChEBI ID48669
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in serine-type endopeptidase activity
Specific function:
Angiostatin is an angiogenesis inhibitor that blocks neovascularization and growth of experimental primary and metastatic tumors in vivo
Gene Name:
PLG
Uniprot ID:
P00747
Molecular weight:
90568.4
References
  1. Dunn CJ, Goa KL: Tranexamic acid: a review of its use in surgery and other indications. Drugs. 1999 Jun;57(6):1005-32. [10400410 ]
  2. Marti DN, Schaller J, Llinas M: Solution structure and dynamics of the plasminogen kringle 2-AMCHA complex: 3(1)-helix in homologous domains. Biochemistry. 1999 Nov 30;38(48):15741-55. [10625440 ]
  3. Jansen AJ, Andreica S, Claeys M, D'Haese J, Camu F, Jochmans K: Use of tranexamic acid for an effective blood conservation strategy after total knee arthroplasty. Br J Anaesth. 1999 Oct;83(4):596-601. [10673876 ]
  4. Bangert K, Thorsen S: Assay of functional plasminogen in rat plasma applicable to experimental studies of thrombolysis. Thromb Haemost. 2000 Aug;84(2):299-306. [10959704 ]
  5. Hanson AJ, Quinn MT: Effect of fibrin sealant composition on human neutrophil chemotaxis. J Biomed Mater Res. 2002 Sep 5;61(3):474-81. [12115473 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]