Tranexamic acid

Identification

Summary

Tranexamic acid is an antifibrinolytic used to reduce or prevent hemorrhagic episodes, especially in the context of hyperfibrinolytic disorders.

Brand Names
Cyklokapron, Lysteda
Generic Name
Tranexamic acid
DrugBank Accession Number
DB00302
Background

Tranexamic acid is a synthetic derivative of lysine used as an antifibrinolytic in the treatment and prevention of major bleeding. It possesses a similar mechanism of action to aminocaproic acid but is approximately 10-fold more potent.6

It was first patented in 19572 and received its initial US approval in 1986.5

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

Taken orally, tranexamic acid is indicated for the treatment of hereditary angioedema,6 cyclic heavy menstrual bleeding in premenopausal females,5 and other instances of significant bleeding in the context of hyperfibrinolysis.6 Given intravenously, tranexamic acid is indicated for short-term use (2-8 days) in patients with hemophilia to prevent or reduce bleeding following tooth extraction.4

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Tranexamic acid is an antifibrinolytic that competitively inhibits the activation of plasminogen to plasmin.5 At much higher concentrations it behaves as a noncompetitive inhibitor of plasmin similar to aminocaproic acid, a similar antifibrinolytic which is 10-fold less potent.6 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. 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).3

Off-target antagonism of GABA(A) receptors may be associated with the development of convulsions and hyperexcitability following tranexamic acid administration1 - the risk appears higher with improper administration or administration during cardiovascular surgery.6 Consider EEG monitoring of patients with a history of seizure.

Mechanism of action

Tranexamic acid competitively and reversibly inhibits the activation of plasminogen via binding at several distinct sites, including four or five low-affinity sites and one high-affinity site, the latter of which is involved in its binding to fibrin. The binding of plasminogen to fibrin induces fibrinolysis - by occupying the necessary binding sites tranexamic acid prevents this dissolution of fibrin, thereby stabilizing the clot and preventing hemorrhage.5

TargetActionsOrganism
APlasminogen
inhibitor
Humans
Absorption

The bioavailability of tranexamic acid after oral administration in humans is approximately 30 to 50% of the ingested dose and is not affected by food intake.5 The Cmax and Tmax following multiple oral doses (1300 mg three times daily x 5 days) were 16.41 mcg/mL and 2.5 h, respectively.5

Volume of distribution

The initial volume of distribution of tranexamic acid is 0.18 L/kg and its steady-state volume of distribution is 0.39 L/kg.5 Tranexamic acid distributes into cerebrospinal fluid and the aqueous humor of the eye at concentrations approximately 1/10th of typical plasma concentrations. Tranexamic acid is also able to cross the placenta, found in cord blood at concentrations equivalent to maternal plasma concentrations.5

Protein binding

Tranexamic acid is approximately 3% protein-bound in plasma at therapeutic concentrations. As it does not bind to serum albumin, it is likely that this protein binding is accounted for by tranexamic acid's binding to serum plasminogen.5

Metabolism

Tranexamic acid metabolism is poorly characterized but does not appear to be a significant means of drug elimination. According to prescribing information, approximately 1% and 0.5% of an orally administered dose are excreted as a dicarboxylic acid and acetylated metabolite, respectively.5

Route of elimination

Urinary excretion is the primary means of tranexamic acid elimination, with >95% of an administered dose excreted in the urine as unchanged parent drug.5 The rate of excretion is dependent on the route of administration - approximately 90% of an intravenously administered dose is excreted within 24 hours whereas only 39% of an orally administered dose is excreted within the same time frame.6

Half-life

Following intravenous administration, the apparent elimination half-life is approximately 2 hours and the mean terminal half-life is approximately 11 hours.5

Clearance

The plasma clearance of tranexamic acid is 110-116 mL/min.5

Adverse Effects
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Toxicity

Reported symptoms of tranexamic acid overdose include severe gastrointestinal symptoms, hypotension, thromboembolism, visual impairment, convulsions, mental status changes, and rash.4,5

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.
AlteplaseThe therapeutic efficacy of Tranexamic acid can be decreased when used in combination with Alteplase.
Aminocaproic acidTranexamic acid may increase the thrombogenic activities of Aminocaproic acid.
Andexanet alfaTranexamic acid may increase the thrombogenic activities of Andexanet alfa.
AnistreplaseThe therapeutic efficacy of Tranexamic acid can be decreased when used in combination with Anistreplase.
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.
Interactions
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Food Interactions
  • Take with or without food. The co-administration of food does not significantly affect tranexamic acid disposition.

Products

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/1mLIntravenousPfizer Laboratories Div Pfizer Inc1986-12-30Not 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 mg/1OralAmring Pharmaceuticals Inc.2010-05-17Not applicableUS flag
LystedaTablet650 mg/1OralXanodyne Pharmaceuticals2010-05-172010-05-17US flag
LystedaTablet650.0 mgOralFerring PharmaceuticalsNot applicableNot applicableCanada flag
LystedaTablet650 mg/1OralFerring Pharmaceuticals Inc.2010-05-172022-12-31US flag
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 AcidInjection100 mg/1mLIntravenousZydus Pharmaceuticals (USA) Inc.2017-10-04Not applicableUS flag
Tranexamic AcidInjection, solution100 mg/1mLIntravenousMylan Institutional LLC2012-12-122012-04-30US flag
Tranexamic AcidTablet650 mg/1OralPrasco Laboratories2010-05-172019-04-30US flag
Tranexamic AcidInjection, solution100 mg/1mLIntravenousApollo Pharmaceuticals Inc.2019-09-30Not applicableUS flag
Tranexamic AcidInjection, solution1 g/10mLIntravenousHeritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc.2014-08-13Not applicableUS flag
Tranexamic AcidInjection, solution100 mg/1mLIntravenousAkorn, Inc.2017-09-28Not applicableUS flag
Tranexamic AcidInjection100 mg/1mLIntravenousMicro Labs Limited2017-08-01Not applicableUS flag
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
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)
Affected organisms
  • Humans and other mammals

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
NC[C@H]1CC[C@@H](CC1)C(O)=O

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
  1. Furtmuller R, Schlag MG, Berger M, Hopf R, Huck S, Sieghart W, Redl H: Tranexamic acid, a widely used antifibrinolytic agent, causes convulsions by a gamma-aminobutyric acid(A) receptor antagonistic effect. J Pharmacol Exp Ther. 2002 Apr;301(1):168-73. doi: 10.1124/jpet.301.1.168. [Article]
  2. Ng W, Jerath A, Wasowicz M: Tranexamic acid: a clinical review. Anaesthesiol Intensive Ther. 2015;47(4):339-50. doi: 10.5603/AIT.a2015.0011. Epub 2015 Mar 23. [Article]
  3. Gompels MM, Lock RJ, Abinun M, Bethune CA, Davies G, Grattan C, Fay AC, Longhurst HJ, Morrison L, Price A, Price M, Watters D: C1 inhibitor deficiency: consensus document. Clin Exp Immunol. 2005 Mar;139(3):379-94. doi: 10.1111/j.1365-2249.2005.02726.x. [Article]
  4. FDA Approved Drug Products: Cyklokapron (tranexamic acid) for intravenous injection [Link]
  5. FDA Approved Drug Products: Lysteda (tranexamic acid) tablets for oral use [Link]
  6. Health Canada Product Monograph: Cyklokapron (tranexamic acid) tablets for oral use [Link]
  7. CaymanChem: Tranexamic acid MSDS [Link]
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 / 6yzc
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
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
4CompletedPreventionBleeding / Prostatectomy1

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
SolutionIntravenous
SolutionOral
SolutionIntravenous500 mg
TabletOral500 mg/1
Injection, solutionParenteral
Tablet, film coatedOral
TabletOral
CapsuleOral
TabletOral650 mg/1
TabletOral650.0 mg
InjectionIntravenous
CreamTopical0.05 mg/50mL
CreamTopical
CreamTopical0.05 g/50mL
LiquidTopical
CapsuleOral250 mg
InjectionIntravenous100 mg/1mL
Injection, solutionIntravenous1 g/10mL
Injection, solutionIntravenous100 mg/1mL
TabletOral650 1/1
Tablet, film coatedOral650 mg/1
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous
Injection, solutionOral
Injection, solution
Tablet, coatedOral
Tablet, film coatedOral500 mg
TabletOral250 mg
CapsuleOral500 mg
Solution
TabletOral500 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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>300 °Chttps://www.caymanchem.com/msdss/19193m.pdf
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

Drugtargets
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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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. FDA Approved Drug Products: Lysteda (tranexamic acid) tablets for oral use [Link]

Drug created on June 13, 2005 13:24 / Updated on May 11, 2021 01:04