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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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cyklokaproninjection, solution100 mg/mLintravenousPharmacia and Upjohn Company1986-12-30Not AvailableUs
Lystedatablet650 mgoralFerring Pharmaceuticals Inc.2010-05-17Not AvailableUs
Lystedatablet650 mgoralFerring Pharmaceuticals Inc.2010-05-17Not AvailableUs
Tranexamic Acidtablet650 mgoralPrasco Laboratories2010-05-17Not AvailableUs
Tranexamic Acidtablet650 mgoralPrasco Laboratories2010-05-17Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Tranexamic Acidinjection, solution100 mg/mLintravenousAmerican Regent, Inc.2011-11-15Not AvailableUs
Tranexamic Acidtablet, film coated650 mgoralActavis Pharma, Inc.2013-01-03Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousNexus Pharmaceuticals Inc2012-03-15Not AvailableUs
Tranexamic Acidinjection, solution1 g/10mLintravenousHeritage Pharmaceuticals Inc.2012-02-20Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousX Gen Pharmaceuticals, Inc.2012-05-18Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousX Gen Pharmaceuticals, Inc.2012-05-18Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousACELLA PHARMACEUTICALS2014-02-11Not AvailableUs
Tranexamic Acidtablet650 1oralGolden State Medical Supply, Inc.2014-08-20Not AvailableUs
Tranexamic Acidtablet650 1oralApotex Corp.2014-01-27Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousFresenius Kabi USA, LLC2012-05-24Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousFresenius Kabi USA, LLC2012-04-20Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousMylan Institutional LLC2011-11-29Not AvailableUs
Tranexamic Acidinjection, solution100 mg/mLintravenousMylan Institutional LLC2011-11-29Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
Cyclo-FNot Available
EspercilNot Available
FemstrualNot Available
RikavarinNot Available
TransaminNot Available
TranscamNot Available
TraxylNot Available
Brand mixturesNot Available
SaltsNot 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
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
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
PropertyValueProbability
Human Intestinal Absorption+0.9538
Blood Brain Barrier+0.8672
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.7572
P-glycoprotein inhibitor INon-inhibitor0.9915
P-glycoprotein inhibitor IINon-inhibitor0.8475
Renal organic cation transporterNon-inhibitor0.7446
CYP450 2C9 substrateNon-substrate0.8862
CYP450 2D6 substrateNon-substrate0.7898
CYP450 3A4 substrateNon-substrate0.829
CYP450 1A2 substrateNon-inhibitor0.9504
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.9577
CYP450 2C19 substrateNon-inhibitor0.9452
CYP450 3A4 substrateNon-inhibitor0.9313
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9698
Ames testNon AMES toxic0.8916
CarcinogenicityNon-carcinogens0.8495
BiodegradationReady biodegradable0.6921
Rat acute toxicity1.0517 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8797
hERG inhibition (predictor II)Non-inhibitor0.9156
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Ferring pharmaceuticals as
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous1 g/10mL
Injection, solutionintravenous100 mg/mL
Tabletoral650 1
Tabletoral650 mg
Tablet, film coatedoral650 mg
Prices
Unit descriptionCostUnit
Cyklokapron 100 mg/ml ampul8.8USD ml
Tranexamic acid powder1.97USD g
Cyklokapron 500 mg Tablet1.3USD tablet
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 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
Mass Spec (NIST)Not Available
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
ATC CodesB02AA02
AHFS Codes
  • 20:28.16
PDB Entries
FDA labelNot Available
MSDSDownload (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