Banner
targets (1) transporters (1)
for drugs
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
Salts Not Available
Brand names
Name Company
Amcha
Amikapron
Amstat
Anvitoff
Carxamin
Cyclocapron
Cyklokapron
Emorhalt
Frenolyse
Mastop
Rikavarin
Rikavarin-S
Tamcha
Tranexan
Transamin
Trasamlon
Ugurol
First Prev Next Last
Brand 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-LJGSYFOKSA-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)/t6-,7-
Plain Text
IUPAC Name
(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid
SMILES
NC[C@H]1CC[C@@H](CC1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point >300 °C PhysProp
water solubility 1.67E+005 mg/L MERCK INDEX (1996)
logP 0.3 Not Available
Predicted Properties
Property Value Source
water solubility 1.82e+01 g/l ALOGPS
logP -1.4 ALOGPS
logP -1.6 ChemAxon
logS -0.94 ALOGPS
pKa (strongest acidic) 4.56 ChemAxon
pKa (strongest basic) 10.22 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 63.32 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 41.9 ChemAxon
polarizability 17.28 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01136 Link_out
ChEBI 48669 Link_out
ChEMBL 48669 Link_out
Therapeutic Targets Database DAP000199 Link_out
PharmGKB PA164750514 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 Not Available
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
Transporters

1. Oligopeptide transporter, kidney isoform

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Dieck ST, Heuer H, Ehrchen J, Otto C, Bauer K: The peptide transporter PepT2 is expressed in rat brain and mediates the accumulation of the fluorescent dipeptide derivative beta-Ala-Lys-Nepsilon-AMCA in astrocytes. Glia. 1999 Jan;25(1):10-20. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 20, 2013 17:05