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Identification
NameTranexamic Acid
Accession NumberDB00302  (APRD01270, EXPT00508)
Typesmall molecule
Groupsapproved
Description

Antifibrinolytic hemostatic used in severe hemorrhage. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
Acide tranexamiqueNot AvailableNot Available
Acido tranexamicoNot AvailableNot Available
Acidum tranexamicumNot AvailableNot Available
CyklokapronNot AvailableNot Available
TranexamsaeureGermanNot Available
Tranexmic acidNot AvailableNot Available
Tranhexamic acidNot AvailableNot Available
Trans AMCHANot AvailableNot Available
trans-4-(Aminomethyl)cyclohexanecarboxylic acidNot AvailableNot Available
trans-4-aminomethylcyclohexane-1-carboxylic acidNot AvailableNot Available
trans-AmchaNot AvailableNot Available
trans-Tranexamic acidNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Cyclo-FNot Available
CyklokapronNot Available
EspercilNot Available
FemstrualNot Available
LystedaNot Available
RikavarinNot Available
TransaminNot Available
TranscamNot Available
TraxylNot Available
Brand mixturesNot Available
Categories
CAS number1197-18-8
WeightAverage: 157.2102
Monoisotopic: 157.110278729
Chemical FormulaC8H15NO2
InChI KeyGYDJEQRTZSCIOI-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-
IUPAC Name
(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid
SMILES
NC[C@H]1CC[C@@H](CC1)C(O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsCarboxylic Acids; Enolates; Monoalkylamines
Substituentsprimary aliphatic amine; primary amine
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
Pharmacology
IndicationFor 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.
PharmacodynamicsTranexamic 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 actionTranexamic 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.
AbsorptionAbsorption 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 bindingThe 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 eliminationUrinary excretion is the main route of elimination via glomerular filtration.
Half lifeBiological half-life in the joint fluid is about 3 hours.
Clearance
  • 110 – 116 mL/min
ToxicityOral 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
PathwayCategorySMPDB ID
Tranexamic Acid Action PathwayDrug actionSMP00287
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9538
Blood Brain Barrier + 0.8672
Caco-2 permeable - 0.8957
P-glycoprotein substrate Non-substrate 0.7572
P-glycoprotein inhibitor I Non-inhibitor 0.9915
P-glycoprotein inhibitor II Non-inhibitor 0.8475
Renal organic cation transporter Non-inhibitor 0.7446
CYP450 2C9 substrate Non-substrate 0.8862
CYP450 2D6 substrate Non-substrate 0.7898
CYP450 3A4 substrate Non-substrate 0.829
CYP450 1A2 substrate Non-inhibitor 0.9504
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9577
CYP450 2C19 substrate Non-inhibitor 0.9452
CYP450 3A4 substrate Non-inhibitor 0.9313
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9698
Ames test Non AMES toxic 0.8916
Carcinogenicity Non-carcinogens 0.8495
Biodegradation Ready biodegradable 0.6921
Rat acute toxicity 1.0517 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8797
hERG inhibition (predictor II) Non-inhibitor 0.9156
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Ferring pharmaceuticals as
Packagers
Dosage forms
FormRouteStrength
SolutionIntravenous
TabletOral
Prices
Unit descriptionCostUnit
Cyklokapron 100 mg/ml ampul8.8USDml
Tranexamic acid powder1.97USDg
Cyklokapron 500 mg Tablet1.3USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point>300 °CPhysProp
water solubility1.67E+005 mg/LMERCK INDEX (1996)
logP0.3Not Available
Predicted Properties
PropertyValueSource
water solubility1.82e+01 g/lALOGPS
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 area63.32ChemAxon
rotatable bond count2ChemAxon
refractivity41.9ChemAxon
polarizability17.28ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Noa Zerangue, Bernd Jandeleit, Yunxiao Li, “Acyloxyalkyl carbamate prodrugs of tranexamic acid, methods of synthesis and use.” U.S. Patent US20070027210, issued February 01, 2007.

US20070027210
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01136
ChEBI48669
ChEMBLCHEMBL877
Therapeutic Targets DatabaseDAP000199
PharmGKBPA164750514
HETAMH
Drug Product Database2064413
RxListhttp://www.rxlist.com/cgi/generic3/cyclapron.htm
Drugs.comhttp://www.drugs.com/cdi/tranexamic-acid.html
WikipediaTranexamic_acid
ATC CodesB02AA02
AHFS Codes
  • 20:28.16
PDB Entries
FDA labelNot Available
MSDSshow(63.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Plasminogen

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Plasminogen P00747 Details

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. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Solute carrier family 15 member 2 Q16348 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09