Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H15NO2 |
Molecular Weight | 157.2102 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC[C@H]1CC[C@@H](CC1)C(O)=O
InChI
InChIKey=GYDJEQRTZSCIOI-LJGSYFOKSA-N
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-
DescriptionSources: http://www.drugbank.ca/drugs/DB00302Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00302
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
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). Tranexamic acid is used 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.
CNS Activity
Sources: http://www.medicines.org.uk/emc/medicine/24325
Curator's Comment: Tranexamic acid crosses the blood brain barrier.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0042730 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8731512 |
60.0 µM [IC50] | ||
Target ID: CHEMBL1801 |
3.1 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LYSTEDA Approved UseLYSTEDA (tranexamic acid) Tablets is an antifibrinolytic indicated for the treatment of cyclic heavy menstrual bleeding. Launch Date5.36198414E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.41 μg/mL |
1300 mg 3 times / day multiple, oral dose: 1300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TRANEXAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
13.83 μg/mL |
1300 mg single, oral dose: 1300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRANEXAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
77.67 μg × h/mL |
1300 mg 3 times / day multiple, oral dose: 1300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TRANEXAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
80.19 μg × h/mL |
1300 mg single, oral dose: 1300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRANEXAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.08 h |
1300 mg single, oral dose: 1300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRANEXAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
97% |
1300 mg single, oral dose: 1300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRANEXAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Other AEs: Headache, Nasal disorder NOS... Other AEs: Headache (50.4%) Sources: Nasal disorder NOS (25.4%) Back pain (20.7%) Abdominal pain (19.8%) Musculoskeletal pain (11.2%) Arthralgia (6.9%) Muscle cramps (6.5%) Migraine (6%) Anemia (5.6%) Fatigue (5.2%) |
1 g 4 times / day steady, oral Overdose Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Sources: |
unhealthy, 45 years n = 1 Health Status: unhealthy Condition: chronic kidney disease Age Group: 45 years Sex: F Population Size: 1 Sources: |
Disc. AE: Convulsions generalized... AEs leading to discontinuation/dose reduction: Convulsions generalized (1 patient) Sources: |
2000 mg 1 times / day steady, intravenous Recommended Dose: 2000 mg, 1 times / day Route: intravenous Route: steady Dose: 2000 mg, 1 times / day Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: emergency operation for a bleeding ulcer of the stomach and duodenum Age Group: 56 years Sex: M Population Size: 1 Sources: |
Disc. AE: Blindness... AEs leading to discontinuation/dose reduction: Blindness (1 patient) Sources: |
250 mg 2 times / day steady, oral Recommended Dose: 250 mg, 2 times / day Route: oral Route: steady Dose: 250 mg, 2 times / day Sources: |
unhealthy, mean 40.7 years n = 561 Health Status: unhealthy Condition: Melasma Age Group: mean 40.7 years Sex: M+F Population Size: 561 Sources: |
Disc. AE: Deep vein thrombosis leg... AEs leading to discontinuation/dose reduction: Deep vein thrombosis leg (1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Musculoskeletal pain | 11.2% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Abdominal pain | 19.8% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Back pain | 20.7% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Nasal disorder NOS | 25.4% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Fatigue | 5.2% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Anemia | 5.6% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Headache | 50.4% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Migraine | 6% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Muscle cramps | 6.5% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Arthralgia | 6.9% | 1300 mg 3 times / day steady, oral Recommended Dose: 1300 mg, 3 times / day Route: oral Route: steady Dose: 1300 mg, 3 times / day Sources: |
healthy, 18 - 49 years n = 232 Health Status: healthy Condition: cyclic heavy menstrual bleeding Age Group: 18 - 49 years Sex: F Population Size: 232 Sources: |
Convulsions generalized | 1 patient Disc. AE |
1 g 4 times / day steady, oral Overdose Dose: 1 g, 4 times / day Route: oral Route: steady Dose: 1 g, 4 times / day Sources: |
unhealthy, 45 years n = 1 Health Status: unhealthy Condition: chronic kidney disease Age Group: 45 years Sex: F Population Size: 1 Sources: |
Blindness | 1 patient Disc. AE |
2000 mg 1 times / day steady, intravenous Recommended Dose: 2000 mg, 1 times / day Route: intravenous Route: steady Dose: 2000 mg, 1 times / day Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: emergency operation for a bleeding ulcer of the stomach and duodenum Age Group: 56 years Sex: M Population Size: 1 Sources: |
Deep vein thrombosis leg | 1 patient Disc. AE |
250 mg 2 times / day steady, oral Recommended Dose: 250 mg, 2 times / day Route: oral Route: steady Dose: 250 mg, 2 times / day Sources: |
unhealthy, mean 40.7 years n = 561 Health Status: unhealthy Condition: Melasma Age Group: mean 40.7 years Sex: M+F Population Size: 561 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
The epileptogenic effect of tranexamic acid. | 1999 Sep |
|
Convulsive seizures following subdural application of fibrin sealant containing tranexamic acid in a rat model. | 2000 Dec |
|
The emerging periplasm-localized subclass of AroQ chorismate mutases, exemplified by those from Salmonella typhimurium and Pseudomonas aeruginosa. | 2001 |
|
A new vascular sealant (Sealgel) to achieve rapid hemostasis after percutaneous angioplasty in anticoagulated patients: clinical feasibility and preliminary results. | 2001 |
|
Retrospective review of the management of elective surgery with desmopressin and clotting factor concentrates in patients with von Willebrand disease. | 2001 Apr |
|
Therapies for the treatment of abnormal uterine bleeding. | 2001 Dec |
|
Dental extractions in patients maintained on oral anticoagulant therapy: comparison of INR value with occurrence of postoperative bleeding. | 2001 Dec |
|
Prevention of the adverse effects of aprotinin in autologous fibrin glue. | 2001 Jan |
|
Congenital alpha(2)-plasmin inhibitor deficiencies: a review. | 2001 Jul |
|
Tranexamic acid in aortic valve replacement. | 2001 Jun |
|
Re: Webster K, Wilde J. Management of anticoagulation in patients with prosthetic heart valves undergoing oral and maxillofacial operations. Br J Oral Maxillofac Surg 2000; 38: 124-126. | 2001 Jun |
|
Plasminogen binding is increased with adipocyte differentiation. | 2001 Jun 8 |
|
Binding diversity of a noncovalent-type low-molecular-weight serine protease inhibitor and function of a catalytic water molecule: X-ray crystal structure of PKSI-527--inhibited trypsin. | 2001 Mar |
|
Intranasal tranexamic acid treatment for severe epistaxis in hereditary hemorrhagic telangiectasia. | 2001 Mar 12 |
|
Successful arthroscopic treatment of pigmented villonodular synovitis of the knee in a patient with congenital deficiency of plasminogen activator inhibitor-1 and recurrent haemarthrosis. | 2001 Mar-Apr |
|
Enhanced thrombolysis induced by argatroban or activated protein C in the presence or absence of staphylokinase, measured in an in vivo animal model using mesenteric arterioles. | 2001 Mar-Apr |
|
Phosphatidylinositol-specific-phospholipase C cleaves urokinase plasminogen activator receptor from the cell surface and leads to inhibition of pemphigus-IgG-induced acantholysis in DJM-1 cells, a squamous cell carcinoma line. | 2001 May |
|
Antifibrinolytic agents and desmopressin as hemostatic agents in cardiac surgery. | 2001 Sep |
|
Drug treatments in upper gastrointestinal bleeding: value of endoscopic findings as surrogate end points. | 2001 Sep |
|
Efficacy of unusually high doses of tranexamic acid for the treatment of epistaxis in hereditary hemorrhagic telangiectasia. | 2001 Sep 20 |
|
Pharmacological strategies to decrease transfusion requirements in patients undergoing surgery. | 2002 |
|
Bleeding from endometrial and vaginal malignant tumors treated with activated recombinant factor VII. | 2002 |
|
Danazol for heavy menstrual bleeding. | 2002 |
|
Desmopressin in the treatment of menorrhagia in women with no common coagulation factor deficiency but with prolonged bleeding time. | 2002 Apr |
|
Pharmacokinetics of tranexamic acid during cardiopulmonary bypass. | 2002 Aug |
|
Epileptic seizures following cortical application of fibrin sealants containing tranexamic acid in rats. | 2002 Jan |
|
Purification and characterization of a novel esterase promising for the production of useful compounds from Microbacterium sp. 7-1W. | 2002 Jan 10 |
|
Oral surgery in patients undergoing oral anticoagulant therapy. | 2002 Jan-Feb |
|
[Pulmonary embolism (PE) associated with urological surgery and angiography]. | 2002 Jul |
|
[Contribution of Japanese researchers to progress in the field of hematology in the last 100 years: Congenital deficiency of alpha2-plasmin inhibitor]. | 2002 Jul 10 |
|
Rendu-Osler-Weber disease: experience with 56 patients. | 2002 Jul-Sep |
|
Menorrhagia. | 2002 Jun |
|
Clinical management of hereditary angio-oedema in children. | 2002 Jun |
|
Hemostatic effects of tranexamic acid in elective thoracic aortic surgery: a prospective, randomized, double-blind, placebo-controlled study. | 2002 Jun |
|
Re: Webster K, Wilde J. Management of anticoagulation in patients with prosthetic heart valves undergoing oral and maxillofacial operations. Br J Oral Maxillofac Surg 2000; 38: 124-126. | 2002 Jun |
|
Acute myocardial infarction after oral tranexamic acid treatment initiation. | 2002 Jun |
|
Acquired factor VIII inhibitors as a cause of primary post-partum haemorrhage. | 2002 Jun 10 |
|
[Continuous infusion of recombinant activated factor VII during and after elbow arthroplasty in a hemophilia A patient with inhibitors]. | 2002 Mar |
|
Development of novel topical tranexamic acid liposome formulations. | 2002 Mar 20 |
|
Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group. | 2002 May 20 |
|
[Familial study of factor XI deficiency. Presurgical prophylactic treatment with desmopressin plus antifibrinolytics]. | 2002 Oct |
|
Impact of hematocrit value after coronary artery surgery on perioperative myocardial infarction rate. | 2002 Oct |
|
Mast cell-derived VEGF enhances the passage of IgE FE-3 through the rat aortic endothelial cell monolayer. | 2002 Sep |
|
A comparison of clinical assessment with ultrasound in the management of secondary postpartum haemorrhage. | 2002 Sep 10 |
|
Effect of fibrin sealant composition on human neutrophil chemotaxis. | 2002 Sep 5 |
|
Safety and efficacy of methods for reducing perioperative allogeneic transfusion: a critical review of the literature. | 2002 Sep-Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: can also be injected http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=TRANEXAMIC%20ACID
1,300 mg (two 650 mg tablets) three times a day (3,900 mg/day) for a
maximum of 5 days during monthly menstruation
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27445340
Curator's Comment: Whole human blood was used
0.03 mg/mL Tranexamic acid reduced the fibrinogen fall induced by t-PA 20 nM from 43% to 14%.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
988
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WHO-ATC |
B02AA02
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WHO-VATC |
QB02AA02
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NDF-RT |
N0000175632
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NDF-RT |
N0000175634
Created by
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WHO-ESSENTIAL MEDICINES LIST |
10.2
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NDF-RT |
N0000175632
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FDA ORPHAN DRUG |
8885
Created by
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NCI_THESAURUS |
C78311
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2713
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PRIMARY | |||
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C47765
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PRIMARY | |||
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10691
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PRIMARY | RxNorm | ||
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SUB11214MIG
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PRIMARY | |||
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6573
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PRIMARY | |||
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CHEMBL877
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PRIMARY | |||
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M11000
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PRIMARY | Merck Index | ||
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Tranexamic Acid
Created by
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PRIMARY | |||
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TRANEXAMIC ACID
Created by
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214-818-2
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291305
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DTXSID3045350
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PRIMARY | |||
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DB00302
Created by
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PRIMARY | |||
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1672745
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6T84R30KC1
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PRIMARY | |||
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D014148
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1197-18-8
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2060
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48669
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6T84R30KC1
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)