Identification

Name
Tranexamic acid
Accession Number
DB00302
Description

Antifibrinolytic hemostatic used in severe hemorrhage.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 157.2102
Monoisotopic: 157.110278729
Chemical Formula
C8H15NO2
Synonyms
  • Acide tranéxamique
  • ácido tranexámico
  • Acidum tranexamicum
  • Tranexamic acid
  • Tranexamsaeure
  • Tranexmic acid
  • Tranhexamic acid
  • Trans AMCHA
  • trans-4-(Aminomethyl)cyclohexanecarboxylic acid
  • trans-4-aminomethylcyclohexane-1-carboxylic acid
  • trans-Amcha
  • trans-Tranexamic acid
External IDs
  • CL 65336
  • CL-65336
  • RP-18429

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.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

TargetActionsOrganism
APlasminogen
inhibitor
Humans
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
Adverse Effects
Learn about our commercial Adverse Effects data.
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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
PathwayCategory
Tranexamic Acid Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Albutrepenonacog alfaTranexamic acid may increase the thrombogenic activities of Albutrepenonacog alfa.
Alpha-1-proteinase inhibitorAlpha-1-proteinase inhibitor may increase the thrombogenic activities of Tranexamic acid.
Aminocaproic acidTranexamic acid may increase the thrombogenic activities of Aminocaproic acid.
Andexanet alfaTranexamic acid may increase the thrombogenic activities of Andexanet alfa.
Anti-inhibitor coagulant complexTranexamic acid may increase the thrombogenic activities of Anti-inhibitor coagulant complex.
Antihemophilic Factor (Recombinant), PEGylatedTranexamic acid may increase the thrombogenic activities of Antihemophilic Factor (Recombinant), PEGylated.
Antihemophilic factor humanTranexamic acid may increase the thrombogenic activities of Antihemophilic factor human.
Antihemophilic factor, human recombinantTranexamic acid may increase the thrombogenic activities of Antihemophilic factor, human recombinant.
AprotininTranexamic acid may increase the thrombogenic activities of Aprotinin.
Beroctocog alfaTranexamic acid may increase the thrombogenic activities of Beroctocog alfa.
Additional Data Available
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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
  • Take with or without food.

Products

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Product Images
International/Other Brands
Cyclo-F / Espercil / Femstrual / Rikavarin / Transamin / Transcam / Traxyl
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CyklokapronInjection, solution100 mg/1mLIntravenousPharmacia and Upjohn Company LLC1986-12-30Not applicableUS flag
CyklokapronTablet500 mg/1OralPharmacia and Upjohn Company2006-01-042006-01-04US flag
Cyklokapron 100 mg/mlSolutionIntravenousPfizer Canada Ulc1995-12-31Not applicableCanada flag
Cyklokapron 500 mgTabletOralPfizer Canada Ulc1995-12-31Not applicableCanada flag
Erfa-tranexamicSolutionIntravenousErfa Canada 2012 Inc2017-07-31Not applicableCanada flag
LystedaTablet650 mg/1OralFerring Pharmaceuticals2010-05-172015-12-31US flag
LystedaTablet650.0 mgOralFerring PharmaceuticalsNot applicableNot applicableCanada flag
LystedaTablet650 mg/1OralXanodyne Pharmaceuticals2010-05-172010-05-17US flag
LystedaTablet650 mg/1OralFerring Pharmaceuticals Inc.2010-05-17Not applicableUS flag
Tranexamic Acid In Sodium ChlorideInjection, solution10 mg/1mLIntravenousExela Pharma Sciences, LLC2019-06-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gd-tranexamic AcidTabletOralGenmed A Division Of Pfizer Canada Ulc2014-03-07Not applicableCanada flag
Gd-tranexamic AcidSolutionIntravenousGenmed A Division Of Pfizer Canada UlcNot applicableNot applicableCanada flag
Mar-tranexamic AcidTabletOralMarcan Pharmaceuticals Inc2020-06-04Not applicableCanada flag
Tranexamic AcidInjection, solution1 g/10mLIntravenousHeritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc.2014-08-13Not applicableUS flag
Tranexamic AcidInjection, solution100 mg/1mLIntravenousFresenius Kabi USA, LLC2012-05-24Not applicableUS flag
Tranexamic AcidTablet650 1/1OralApotex Corp.2014-01-272022-03-31US flag60505 363820180907 15195 1y6dn2v
Tranexamic AcidInjection, solution100 mg/1mLIntravenousAkorn, Inc.2015-03-09Not applicableUS flag
Tranexamic AcidInjection100 mg/1mLIntravenousCadila Healthcare Limited2017-10-04Not applicableUS flag
Tranexamic AcidInjection, solution100 mg/1mLIntravenousAthenex Pharmaceutical Division, Llc.2017-03-27Not applicableUS flag
Tranexamic AcidInjection, solution100 mg/1mLIntravenousXGen Pharmaceuticals DJB, Inc.2012-05-18Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

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  • Product Code
    Product Code
    Available for Purchase

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Pure Whitenol SerumCream0.05 mg/50mLTopicalSkin M.D. Korea2015-02-01Not applicableUS flag
Skinmd Laboratories Pure Whitenol SerumCream0.05 g/50mLTopicalReviresco Co., Ltd.2017-12-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Skinmd Laboratories Pure Whitenol IntensiveTranexamic acid (0.02 g/10mL) + Adenosine (0.004 g/10mL)CreamTopicalReviresco Co., Ltd.2017-12-01Not applicableUS flag
SKINMD LABORATORIES ReviTox blueTranexamic acid (0.001 g/10mL) + Adenosine (0.004 g/10mL)LiquidTopicalReviresco Co., Ltd.2017-12-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Pure Whitenol SerumTranexamic acid (0.05 mg/50mL)CreamTopicalSkin M.D. Korea2015-02-01Not applicableUS flag
Skinmd Laboratories Pure Whitenol IntensiveTranexamic acid (0.02 g/10mL) + Adenosine (0.004 g/10mL)CreamTopicalReviresco Co., Ltd.2017-12-01Not applicableUS flag
Skinmd Laboratories Pure Whitenol SerumTranexamic acid (0.05 g/50mL)CreamTopicalReviresco Co., Ltd.2017-12-01Not applicableUS flag
SKINMD LABORATORIES ReviTox blueTranexamic acid (0.001 g/10mL) + Adenosine (0.004 g/10mL)LiquidTopicalReviresco Co., Ltd.2017-12-01Not applicableUS flag

Categories

ATC Codes
B02AA02 — Tranexamic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Amino acids
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic homomonocyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:48669)

Chemical Identifiers

UNII
6T84R30KC1
CAS number
1197-18-8
InChI Key
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-
IUPAC Name
(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid
SMILES

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 References
Not Available
Human Metabolome Database
HMDB0014447
KEGG Drug
D01136
PubChem Compound
5526
PubChem Substance
46508089
ChemSpider
10482000
BindingDB
50428067
RxNav
10691
ChEBI
48669
ChEMBL
CHEMBL877
ZINC
ZINC000100071256
Therapeutic Targets Database
DAP000199
PharmGKB
PA164750514
PDBe Ligand
AMH
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tranexamic_acid
AHFS Codes
  • 20:28.16 — Hemostatics
PDB Entries
1b2i / 1ceb / 5v3c / 6nmb
MSDS
Download (63.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAnterior Cruciate Ligament Rupture1
4Active Not RecruitingTreatmentBlood Loss,Surgical1
4Active Not RecruitingTreatmentFracture of Femur1
4Active Not RecruitingTreatmentHeavy Menstrual Bleeding / Hypermenorrhea / Uterine Leiomyomas1
4CompletedNot AvailableHypermenorrhea1
4CompletedOtherComplication of Extracorporeal Circulation / Pediatric Cardiac Surgery1
4CompletedOtherRevision Total Hip Arthroplasty (RTHA)1
4CompletedPreventionAdenoidectomy / Tonsillectomy / Tranexamic Acid1
4CompletedPreventionBiliary Tract Surgical Procedures / Colectomy / Gastric Resection / Oesophagectomy / Pancreatoduodenectomy1
4CompletedPreventionBleeding1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
  • Ferring pharmaceuticals as
Packagers
  • Gallipot
  • Pfizer Inc.
  • Pharmacia Inc.
  • Professional Compounding Centers America LLC
  • Xanodyne Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
TabletOral500 mg
Injection, solutionParenteral100 MG/ML
SolutionIntravenous500 mg
TabletOral500 mg/1
SolutionIntravenous
TabletOral
Tablet, coatedOral500 mg
Injection, solutionIntravenous250 mg/2.5ml
TabletOral650 mg/1
TabletOral650.0 mg
InjectionIntravenous100 MG/ML
CreamTopical0.05 mg/50mL
CreamTopical
CreamTopical0.05 g/50mL
LiquidTopical
CapsuleOral250 MG
CapsuleOral500 MG
Injection, solution500 MG/5ML
InjectionIntravenous100 mg/1mL
InjectionIntravenous50 MG/ML
Injection, solutionIntravenous1 g/10mL
Injection, solutionIntravenous100 mg/1mL
TabletOral650 1/1
Tablet, film coatedOral
Tablet, film coatedOral650 mg/1
Injection, solutionIntravenous500 mg/5mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous500 mg
Injection, solutionIntravenous250 mg/5ml
Injection, solution250 mg/5mL
InjectionIntravenous50 MG
InjectionIntravenous100 MG
Injection, solutionIntravenous10 %
Injection, solutionIntravenous100 mg/mL
Injection, solutionIntravenous50 mg/mL
Tablet, film coatedOral500 mg
Injection, solutionOral500 MG/5ML
TabletOral250 MG
CreamTopical5 g/100g
SolutionIntravenous100 mg/mL
SolutionIntravenous100 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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8022106No2011-09-202025-03-04US flag
US8273795No2012-09-252025-03-04US flag
US8487005No2013-07-162025-03-04US flag
US8791160No2014-07-292025-03-04US flag
US8809394No2014-08-192025-03-04US flag
US8957113No2015-02-172025-03-04US flag
US9060939No2015-06-232025-03-04US flag
US7947739No2011-05-242025-03-04US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9577
CYP450 2C19 inhibitorNon-inhibitor0.9452
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Details
1. Plasminogen
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type peptidase activity
Specific Function
Plasmin dissolves the fibrin of blood clots and acts as a proteolytic factor in a variety of other processes including embryonic development, tissue remodeling, tumor invasion, and inflammation. In...
Gene Name
PLG
Uniprot ID
P00747
Uniprot Name
Plasminogen
Molecular Weight
90568.415 Da
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: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12115473]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
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:9888294]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2020 00:54

Cs molecular health 1