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-
| Molecular Formula | C8H15NO2 |
| Molecular Weight | 157.2102 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0042730 |
60.0 µM [IC50] | ||
| 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 Date1986 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
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 |
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 |
|---|---|---|
| Rendu-Osler-Weber disease: experience with 56 patients. | 2002-10-31 |
|
| [Familial study of factor XI deficiency. Presurgical prophylactic treatment with desmopressin plus antifibrinolytics]. | 2002-10 |
|
| Impact of hematocrit value after coronary artery surgery on perioperative myocardial infarction rate. | 2002-10 |
|
| Successful treatment of acute promyelocytic leukaemia during pregnancy. | 2002-10 |
|
| Safety and efficacy of methods for reducing perioperative allogeneic transfusion: a critical review of the literature. | 2002-09-19 |
|
| A comparison of clinical assessment with ultrasound in the management of secondary postpartum haemorrhage. | 2002-09-10 |
|
| Effect of fibrin sealant composition on human neutrophil chemotaxis. | 2002-09-05 |
|
| Mast cell-derived VEGF enhances the passage of IgE FE-3 through the rat aortic endothelial cell monolayer. | 2002-09 |
|
| Tranexamic acid reduces bleeding and the need for blood transfusion in primary myocardial revascularization. | 2002-09 |
|
| Is the kaolin or celite activated clotting time affected by tranexamic acid? | 2002-08 |
|
| Differential effects of aprotinin and tranexamic acid on endotoxin desensitization of blood cells induced by circulation through an isolated extracorporeal circuit. | 2002-08 |
|
| Pharmacokinetics of tranexamic acid during cardiopulmonary bypass. | 2002-08 |
|
| [Contribution of Japanese researchers to progress in the field of hematology in the last 100 years: Congenital deficiency of alpha2-plasmin inhibitor]. | 2002-07-10 |
|
| [Pulmonary embolism (PE) associated with urological surgery and angiography]. | 2002-07 |
|
| Acquired factor VIII inhibitors as a cause of primary post-partum haemorrhage. | 2002-06-10 |
|
| Menorrhagia. | 2002-06 |
|
| Clinical management of hereditary angio-oedema in children. | 2002-06 |
|
| Hemostatic effects of tranexamic acid in elective thoracic aortic surgery: a prospective, randomized, double-blind, placebo-controlled study. | 2002-06 |
|
| 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. | 2002-06 |
|
| Primary intestinal and thoracic lymphangiectasia: a response to antiplasmin therapy. | 2002-06 |
|
| Acute myocardial infarction after oral tranexamic acid treatment initiation. | 2002-06 |
|
| Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group. | 2002-05-20 |
|
| Pulmonary embolism associated with tranexamic acid in severe acquired haemophilia. | 2002-05 |
|
| Tranexamic acid in patients with hemoptysis. | 2002-04 |
|
| Desmopressin in the treatment of menorrhagia in women with no common coagulation factor deficiency but with prolonged bleeding time. | 2002-04 |
|
| Tranexamic acid, a widely used antifibrinolytic agent, causes convulsions by a gamma-aminobutyric acid(A) receptor antagonistic effect. | 2002-04 |
|
| Development of novel topical tranexamic acid liposome formulations. | 2002-03-20 |
|
| The two-domain NK1 fragment of plasminogen: folding, ligand binding, and thermal stability profile. | 2002-03-12 |
|
| [Continuous infusion of recombinant activated factor VII during and after elbow arthroplasty in a hemophilia A patient with inhibitors]. | 2002-03 |
|
| von Willebrand's disease: an important cause of dysfunctional uterine bleeding. | 2002-03 |
|
| Does tranexamic acid reduce desmopressin-induced hyperfibrinolysis? | 2002-03 |
|
| Tranexamic acid in hereditary hemorrhagic telangiectasia. | 2002-02-07 |
|
| Differences between neonates and adults in carbohydrate sequences and reaction kinetics of plasmin and alpha(2)-antiplasmin. | 2002-02-01 |
|
| Oral surgery in patients undergoing oral anticoagulant therapy. | 2002-01-15 |
|
| [Tranexamic acid reduces blood loss and the need of blood transfusion after knee arthroplasty]. | 2002-01-14 |
|
| Purification and characterization of a novel esterase promising for the production of useful compounds from Microbacterium sp. 7-1W. | 2002-01-10 |
|
| Epileptic seizures following cortical application of fibrin sealants containing tranexamic acid in rats. | 2002-01 |
|
| 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 |
|
| Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding. | 2002 |
|
| The effect of tranexamic acid on the quality of life of women with heavy menstrual bleeding. | 2001-12-01 |
|
| Systematic elucidation of effects of tranexamic acid on fibrinolysis and bleeding during and after cardiopulmonary bypass surgery. | 2001-12-01 |
|
| Therapies for the treatment of abnormal uterine bleeding. | 2001-12 |
|
| Dental extractions in patients maintained on oral anticoagulant therapy: comparison of INR value with occurrence of postoperative bleeding. | 2001-12 |
|
| Possible role of plasminogen activator in the occurrence of profuse watery rhinorrhea after topical application of epinephrine to the nasal mucosa. | 2001-12 |
|
| Isolation, quantitation, and characterization of a stable complex formed by Lp[a] binding to triglyceride-rich lipoproteins. | 2001-12 |
|
| Influence of Helicobacter pylori infection and cetraxate on gastric mucosal blood flow during healing of endoscopic mucosal resection-induced ulcers. | 2001-11 |
|
| The use of technologies to decrease peri-operative allogenic blood transfusion: results of practice variation in Israel. | 2001-11 |
|
| Blood conservation with tranexamic acid in total hip arthroplasty: a randomized, double-blind study in 40 primary operations. | 2001-10 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 08:34:29 GMT 2025
by
admin
on
Wed Apr 02 08:34:29 GMT 2025
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| Record UNII |
6T84R30KC1
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| Record Status |
Validated (UNII)
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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
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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
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NCI_THESAURUS |
C78311
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2713
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C47765
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10691
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SUB11214MIG
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6573
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CHEMBL877
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m11000
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Tranexamic Acid
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TRANEXAMIC ACID
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214-818-2
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291305
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DTXSID3045350
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DB00302
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1672745
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6T84R30KC1
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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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100000091040
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
|
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
||
|
TARGET -> INHIBITOR |
Inhibits fibrinolysis by blocking the binding site of lysine on plasminogen.
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE -> PARENT |
One percent percent of an oral dose are excreted as a dicarboxylic acid
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
|
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|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
UNSPECIFIED
EP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |