U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of TRANEXAMIC ACID

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-

HIDE SMILES / InChI

Description
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

CNS Penetrant
2588
Curator's Comment: Tranexamic acid crosses the blood brain barrier.

Originator

Approval Year

1986
107
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 60.0 µM [IC50]
Inhibitor
8504
 3.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
LYSTEDA

Approved Use

LYSTEDA (tranexamic acid) Tablets is an antifibrinolytic indicated for the treatment of cyclic heavy menstrual bleeding.

Launch Date

1986
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.83 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
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

AUC

ValueDoseCo-administeredAnalytePopulation
80.19 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
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

T1/2

ValueDoseCo-administeredAnalytePopulation
11.08 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
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

Funbound

ValueDoseCo-administeredAnalytePopulation
97%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022430s004lbl.pdf
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2A6
879

CYP2C19
2057

CYP2E1
1060

OATP1B1
1079

OATP1B3
961
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [IC50 >10 uM]
CYP2A6
911
 no [IC50 >10 uM]
CYP2C19
2141
 no [IC50 >10 uM]
CYP2C9
2497
 no [IC50 >10 uM]
CYP2D6
2546
 no [IC50 >10 uM]
CYP2E1
1146
 no [IC50 >10 uM]
CYP3A4
2633
 no [IC50 >10 uM]
OATP1B1
1095
 yes
OATP1B3
970
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:48669
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48669
ChemicalBook
CB1117189
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1117189
ChemicalBook
CB2948513
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2948513
ChemicalBook
CB54848494
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB54848494
eMolecules
476513
https://www.emolecules.com/cgi-bin/more?vid=476513
MolPort
MolPort-002-512-008
https://www.molport.com/shop/molecule-link/MolPort-002-512-008
Selleck Chemicals
tranexamic-acid-transamin
http://www.selleckchem.com/products/tranexamic-acid-transamin.html
ZINC
ZINC000100071256
http://zinc15.docking.org/substances/ZINC000100071256
PubMed

PubMed

TitleDatePubMed
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

Patents

05367072
1
05488055
2
05534498
1
05707966
1
05714580
1
05721214
1
06211241
1
06559168
2
06894041
2
07592369
1
07737161
1
JP2000256163A
1
JP2002145759A
5
JP2004217655A
1
JP2005068076A
1
JP2005075771A
1
JP2006076938A
1
JP2006104141A
2
JP2006312603A
1
JP2007145758A
1
JP2007169201A
6
JP2009051795A
1
JP2009143965A
1
JP2009242360A
1
JP2009509661A
3
JP2010100564A
1
JP2010189301A
1
JP2011016786A
1
JP2011225529A
1
JPH00343082A
1
JPH01186811A
8
JPH0193519A
1
JPH03197423A
1
JPH03279313A
1
JPH04139117A
2
JPH04300815A
1
JPH0441468A
1
JPH0672846A
1
JPH0672847A
1
JPH0672975A
1
JPH08295689A
1
JPH0840821A
1
JPH0912432A
1
JPH09281103A
1
JPH09510696A
1
JPH0995429A
1
JPS55151539A
1
JPS5646816A
1
JPS5753440A
1
JPS6259289A
1
JPS63313761A
1

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
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%.
Name Type Language
TRANEXAMIC ACID
EP   INCI   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   INCI   USAN  
Official Name English
RIKAVARIN
Preferred Name English
TRANEXAMIC ACID [USP MONOGRAPH]
Common Name English
TRANEXAMIC ACID [USP-RS]
Common Name English
TRANS-4-(AMINOMETHYL)CYCLOHEXANECARBOXYLIC ACID
Systematic Name English
CYCLOHEXANECARBOXYLIC ACID, 4-(AMINOMETHYL)-, TRANS-
Systematic Name English
CYCLO-F
Brand Name English
tranexamic acid [INN]
Common Name English
RP-18429
Code English
AMCHA
Common Name English
TRANEXAMIC ACID [USAN]
Common Name English
TRANSAMIN
Brand Name English
LYSTEDA
Brand Name English
NSC-291305
Code English
TRANEXAMIC ACID [USP IMPURITY]
Common Name English
TRANEXAMIC ACID [ORANGE BOOK]
Common Name English
HAEMATRIX
Brand Name English
CYCLOCAPRON
Common Name English
CL65336
Code English
TRANEXAMIC ACID [MART.]
Common Name English
CL-65336
Code English
CYKLOKAPRON
Brand Name English
TRANS-AMCHA
Code English
ESPERCIL
Brand Name English
TRANEXAMIC ACID [VANDF]
Common Name English
TRANEXAMIC ACID [EP MONOGRAPH]
Common Name English
TRANEXAMIC ACID [JAN]
Common Name English
LB1148
Code English
CYCLOKAPRON
Common Name English
Tranexamic acid [WHO-DD]
Common Name English
TRANEXAMIC ACID [MI]
Common Name English
FEMSTRUAL
Brand Name English
TRANS AMCHA
Code English
Classification Tree Code System Code
LIVERTOX 988
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
WHO-ATC B02AA02
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
WHO-VATC QB02AA02
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
NDF-RT N0000175632
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
NDF-RT N0000175634
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 10.2
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
NDF-RT N0000175632
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
FDA ORPHAN DRUG 8885
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
NCI_THESAURUS C78311
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2713
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
NCI_THESAURUS
C47765
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
RXCUI
10691
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY RxNorm
EVMPD
SUB11214MIG
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
IUPHAR
6573
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
ChEMBL
CHEMBL877
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
MERCK INDEX
m11000
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY Merck Index
LACTMED
Tranexamic Acid
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
WIKIPEDIA
TRANEXAMIC ACID
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
ECHA (EC/EINECS)
214-818-2
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
NSC
291305
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
EPA CompTox
DTXSID3045350
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
DRUG BANK
DB00302
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
RS_ITEM_NUM
1672745
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
DAILYMED
6T84R30KC1
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
MESH
D014148
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
CAS
1197-18-8
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
INN
2060
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
CHEBI
48669
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
FDA UNII
6T84R30KC1
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
SMS_ID
100000091040
Created by admin on Wed Apr 02 08:34:29 GMT 2025 , Edited by admin on Wed Apr 02 08:34:29 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of TRANEXAMIC ACID
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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