Tranexamic acid
Identification
- Name
- Tranexamic acid
- Accession Number
- DB00302
- Description
Antifibrinolytic hemostatic used in severe hemorrhage.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Tranexamic acid (DB00302)
- 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.
Learn More- 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.
Target Actions Organism APlasminogen inhibitorHumans - 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.
Learn More- 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 Category Tranexamic Acid Action Pathway Drug 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.
Drug Interaction Unlock Additional DataAlbutrepenonacog alfa Tranexamic acid may increase the thrombogenic activities of Albutrepenonacog alfa. Alpha-1-proteinase inhibitor Alpha-1-proteinase inhibitor may increase the thrombogenic activities of Tranexamic acid. Aminocaproic acid Tranexamic acid may increase the thrombogenic activities of Aminocaproic acid. Andexanet alfa Tranexamic acid may increase the thrombogenic activities of Andexanet alfa. Anti-inhibitor coagulant complex Tranexamic acid may increase the thrombogenic activities of Anti-inhibitor coagulant complex. Antihemophilic Factor (Recombinant), PEGylated Tranexamic acid may increase the thrombogenic activities of Antihemophilic Factor (Recombinant), PEGylated. Antihemophilic factor human Tranexamic acid may increase the thrombogenic activities of Antihemophilic factor human. Antihemophilic factor, human recombinant Tranexamic acid may increase the thrombogenic activities of Antihemophilic factor, human recombinant. Aprotinin Tranexamic acid may increase the thrombogenic activities of Aprotinin. Beroctocog alfa Tranexamic acid may increase the thrombogenic activities of Beroctocog alfa. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with or without food.
Products
- Product Images
- International/Other Brands
- Cyclo-F / Espercil / Femstrual / Rikavarin / Transamin / Transcam / Traxyl
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCyklokapron Injection, solution 100 mg/1mL Intravenous Pharmacia and Upjohn Company LLC 1986-12-30 Not applicable US 
Cyklokapron Tablet 500 mg/1 Oral Pharmacia and Upjohn Company 2006-01-04 2006-01-04 US Cyklokapron 100 mg/ml Solution Intravenous Pfizer Canada Ulc 1995-12-31 Not applicable Canada 
Cyklokapron 500 mg Tablet Oral Pfizer Canada Ulc 1995-12-31 Not applicable Canada Erfa-tranexamic Solution Intravenous Erfa Canada 2012 Inc 2017-07-31 Not applicable Canada Lysteda Tablet 650 mg/1 Oral Xanodyne Pharmaceuticals 2010-05-17 2010-05-17 US Lysteda Tablet 650 mg/1 Oral Ferring Pharmaceuticals Inc. 2010-05-17 Not applicable US Lysteda Tablet 650.0 mg Oral Ferring Pharmaceuticals Not applicable Not applicable Canada Lysteda Tablet 650 mg/1 Oral Ferring Pharmaceuticals 2010-05-17 2015-12-31 US Tranexamic Acid In Sodium Chloride Injection, solution 10 mg/1mL Intravenous Exela Pharma Sciences, LLC 2019-06-01 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataGd-tranexamic Acid Solution Intravenous Genmed A Division Of Pfizer Canada Ulc Not applicable Not applicable Canada Gd-tranexamic Acid Tablet Oral Genmed A Division Of Pfizer Canada Ulc 2014-03-07 Not applicable Canada Mar-tranexamic Acid Tablet Oral Marcan Pharmaceuticals Inc 2020-06-04 Not applicable Canada Tranexamic Acid Injection, solution 100 mg/1mL Intravenous AMERICAN REGENT, INC. 2011-11-15 Not applicable US Tranexamic Acid Injection, solution 100 mg/1mL Intravenous Methapharm, Inc. 2019-03-11 Not applicable US Tranexamic Acid Tablet 650 mg/1 Oral Prasco Laboratories 2010-05-17 2019-04-30 US Tranexamic Acid Injection 100 mg/1mL Intravenous Micro Labs Limited 2017-08-01 Not applicable US Tranexamic Acid Injection, solution 100 mg/1mL Intravenous Akorn 2016-06-09 Not applicable US Tranexamic Acid Injection, solution 100 mg/1mL Intravenous XGen Pharmaceuticals DJB, Inc. 2012-05-18 Not applicable US Tranexamic Acid Tablet 650 mg/1 Oral Amring Pharmaceuticals, Inc. 2016-03-01 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataPure Whitenol Serum Cream 0.05 mg/50mL Topical Skin M.D. Korea 2015-02-01 Not applicable US Skinmd Laboratories Pure Whitenol Serum Cream 0.05 g/50mL Topical Reviresco Co., Ltd. 2017-12-01 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Skinmd Laboratories Pure Whitenol Intensive Tranexamic acid (0.02 g/10mL) + Adenosine (0.004 g/10mL) Cream Topical Reviresco Co., Ltd. 2017-12-01 Not applicable US SKINMD LABORATORIES ReviTox blue Tranexamic acid (0.001 g/10mL) + Adenosine (0.004 g/10mL) Liquid Topical Reviresco Co., Ltd. 2017-12-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Pure Whitenol Serum Tranexamic acid (0.05 mg/50mL) Cream Topical Skin M.D. Korea 2015-02-01 Not applicable US Skinmd Laboratories Pure Whitenol Intensive Tranexamic acid (0.02 g/10mL) + Adenosine (0.004 g/10mL) Cream Topical Reviresco Co., Ltd. 2017-12-01 Not applicable US Skinmd Laboratories Pure Whitenol Serum Tranexamic acid (0.05 g/50mL) Cream Topical Reviresco Co., Ltd. 2017-12-01 Not applicable US SKINMD LABORATORIES ReviTox blue Tranexamic acid (0.001 g/10mL) + Adenosine (0.004 g/10mL) Liquid Topical Reviresco Co., Ltd. 2017-12-01 Not applicable US
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
- NC[[email protected]]1CC[[email protected]@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
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014447
- KEGG Drug
- D01136
- PubChem Compound
- 5526
- PubChem Substance
- 46508089
- ChemSpider
- 10482000
- BindingDB
- 50428067
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Anterior Cruciate Ligament Rupture 1 4 Active Not Recruiting Treatment Blood Loss,Surgical 1 4 Active Not Recruiting Treatment Fracture of Femur 1 4 Active Not Recruiting Treatment Heavy Menstrual Bleeding / Hypermenorrhea / Uterine Leiomyomas 1 4 Completed Not Available Hypermenorrhea 1 4 Completed Other Complication of Extracorporeal Circulation / Pediatric Cardiac Surgery 1 4 Completed Other Revision Total Hip Arthroplasty (RTHA) 1 4 Completed Prevention Adenoidectomy / Tonsillectomy / Tranexamic Acid 1 4 Completed Prevention Biliary Tract Surgical Procedures / Colectomy / Gastric Resection / Oesophagectomy / Pancreatoduodenectomy 1 4 Completed Prevention Bleeding 1
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
Form Route Strength Tablet Oral 500 mg Injection, solution Parenteral 100 MG/ML Solution Intravenous 500 mg Tablet Oral 500 mg/1 Solution Intravenous Tablet Oral Tablet, film coated Oral 500 mg Tablet, coated Oral 500 mg Injection, solution Intravenous 250 mg/2.5ml Capsule Tablet Oral 650 mg/1 Tablet Oral 650.0 mg Tablet Cream Topical 0.05 mg/50mL Cream Topical Cream Topical 0.05 g/50mL Liquid Topical Capsule 500 mg Capsule Oral 250 MG Capsule Oral 500 MG Injection, solution 500 MG/5ML Injection Intravenous 100 mg/1mL Injection, solution Intravenous 1 g/10mL Injection, solution Intravenous 100 mg/1mL Tablet Oral 650 1/1 Tablet, film coated Oral Tablet, film coated Oral 650 mg/1 Injection, solution Intravenous 10 mg/1mL Injection, solution Intravenous 250 mg/5ml Capsule 250 mg Injection, solution 250 mg/5mL Capsule Oral Injection, solution Intravenous 100 mg/mL Injection, solution Intravenous 50 mg/mL Tablet, film coated 500 mg Injection Injection, solution Oral 500 MG/5ML Tablet Oral 250 MG Cream 5 g/100g Solution Intravenous 100 mg/mL Solution Intravenous 100 mg - Prices
Unit description Cost Unit Cyklokapron 100 mg/ml ampul 8.8USD ml Tranexamic acid powder 1.97USD g Cyklokapron 500 mg Tablet 1.3USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS8022106 No 2011-09-20 2025-03-04 US US8273795 No 2012-09-25 2025-03-04 US US8487005 No 2013-07-16 2025-03-04 US US8791160 No 2014-07-29 2025-03-04 US US8809394 No 2014-08-19 2025-03-04 US US8957113 No 2015-02-17 2025-03-04 US US9060939 No 2015-06-23 2025-03-04 US US7947739 No 2011-05-24 2025-03-04 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >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 18.2 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 41.9 m3·mol-1 ChemAxon Polarizability 17.28 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9577 CYP450 2C19 inhibitor Non-inhibitor 0.9452 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- 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 October 21, 2020 01:55
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