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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

Molecular Formula C8H15NO2
Molecular Weight 157.2102
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
60.0 µM [IC50]
3.1 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LYSTEDA

Cmax

ValueDoseCo-administeredAnalytePopulation
13.83 μg/mL
1300 mg single, oral
TRANEXAMIC ACID plasma
Homo sapiens
16.41 μg/mL
1300 mg 3 times / day multiple, oral
TRANEXAMIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
80.19 μg × h/mL
1300 mg single, oral
TRANEXAMIC ACID plasma
Homo sapiens
77.67 μg × h/mL
1300 mg 3 times / day multiple, oral
TRANEXAMIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.08 h
1300 mg single, oral
TRANEXAMIC ACID plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
97%
1300 mg single, oral
TRANEXAMIC ACID plasma
Homo sapiens

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
0.03 mg/mL Tranexamic acid reduced the fibrinogen fall induced by t-PA 20 nM from 43% to 14%.
Substance Class Chemical
Record UNII
6T84R30KC1
Record Status Validated (UNII)
Record Version