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Identification
Name Tranexamic Acid
Accession Number DB00302 (APRD01270, EXPT00508)
Type small molecule
Groups approved
Description

Antifibrinolytic hemostatic used in severe hemorrhage. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Tranexamsaeure
  • tranexmic acid
  • Tranhexamic acid
  • Trans AMCHA
  • trans-4-aminomethylcyclohexane-1-carboxylic acid
  • trans-Amcha
  • trans-Tranexamic acid
Brand names
  • Amcha
  • Amikapron
  • Amstat
  • Anvitoff
  • Carxamin
  • Cyclocapron
  • Cyklokapron
  • Emorhalt
  • Frenolyse
  • Mastop
  • Rikavarin
  • Rikavarin-S
  • Tamcha
  • Tranexan
  • Transamin
  • Trasamlon
  • Ugurol
Brand name mixtures Not Available
Categories
  • Antifibrinolytic Agents
CAS number 1197-18-8
Weight Average: 157.2102
Monoisotopic: 157.110278729
Chemical Formula C8H15NO2
InChI Key InChIKey=GYDJEQRTZSCIOI-UHFFFAOYSA-N
InChI
InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)
Plain Text
IUPAC Name
4-(aminomethyl)cyclohexane-1-carboxylic acid
SMILES
NCC1CCC(CC1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
Pharmacology
Indication For use in patients with hemophilia for short term use (two to eight days) to reduce or prevent hemorrhage and reduce the need for replacement therapy during and following tooth extraction. It can also be used for excessive bleeding in menstruation, surgery, or trauma cases.
Pharmacodynamics Tranexamic acid is an antifibrinolytic that competitively inhibits the activation of plasminogen to plasmin. Tranexamic acid is a competitive inhibitor of plasminogen activation, and at much higher concentrations, a noncompetitive inhibitor of plasmin, i.e., actions similar to aminocaproic acid. Tranexamic acid is about 10 times more potent in vitro than aminocaproic acid. Tranexamic acid binds more strongly than aminocaproic acid to both the strong and weak receptor sites of the plasminogen molecule in a ratio corresponding to the difference in potency between the compounds. Tranexamic acid in a concentration of 1 mg per mL does not aggregate platelets in vitro. In patients with hereditary angioedema, inhibition of the formation and activity of plasmin by tranexamic acid may prevent attacks of angioedema by decreasing plasmin-induced activation of the first complement protein (C1).
Mechanism of action 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.
Absorption Absorption of tranexamic acid after oral administration in humans represents approximately 30 to 50% of the ingested dose and bioavailability is not affected by food intake.
Volume of distribution
  • 9 to 12 L
Protein binding The plasma protein binding of tranexamic acid is about 3% at therapeutic plasma levels and seems to be fully accounted for by its binding to plasminogen (does not bind serum albumin).
Metabolism

Only a small fraction of the drug is metabolized (less than 5%).
Route of elimination Urinary excretion is the main route of elimination via glomerular filtration.
Half life Biological half-life in the joint fluid is about 3 hours.
Clearance
  • 110 – 116 mL/min
Toxicity Oral LD50 in mice is >10 gm/kg. Symptoms of overdosage may be nausea, vomiting, orthostatic symptoms and/or hypotension.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00287 Tranexamic Acid Pathway SMP00287
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Ferring pharmaceuticals as
Packagers
Dosage forms
Form Route Strength
Solution Intravenous
Tablet Oral
Prices
Unit description Cost Unit
Cyklokapron 100 mg/ml ampul 8.8 USD ml
Tranexamic acid powder 1.97 USD g
Cyklokapron 500 mg Tablet 1.3 USD tablet
Patents Not Available
Properties
State solid
Melting point >300 oC
Experimental Properties
Property Value Source
water solubility 1.67E+005 mg/L PhysProp
logP 0.3 PhysProp
Predicted Properties
Property Value Source
water solubility 1.82e+01 g/l ALOGPS
logP -1.42 ALOGPS
logP -2.32 ChemAxon Molconvert
logS -0.94 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 63.32 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 41.90 ChemAxon Molconvert
polarizability 17.28 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01136 Link_out
PubChem Compound 5526 Link_out
PubChem Substance 46508089 Link_out
ChemSpider 5325 Link_out
ChEBI 48669 Link_out
ChEMBL 48669 Link_out
Therapeutic Targets Database DAP000199 Link_out
PharmGKB PA451738 Link_out
HET AMH Link_out
Drug Product Database 2064413 Link_out
RxList http://www.rxlist.com/cgi/generic3/cyclapron.htm Link_out
Drugs.com http://www.drugs.com/cdi/tranexamic-acid.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Tranexamic_acid Link_out
ATC Codes
  • B02AA02
AHFS Codes
  • 20:28.16
PDB Entries
FDA label Not Available
MSDS show (63.5 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Plasminogen

Pharmacological action: yes
Actions: inhibitor

Angiostatin is an angiogenesis inhibitor that blocks neovascularization and growth of experimental primary and metastatic tumors in vivo

Organism class: human
UniProt ID: P00747 Link_out
Gene: PLG Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:02

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.