tranexamic acid

Also known as CL-65336, Cyclo-F®, Cyklokapron®, Femstrual®, trans AMCHA, trans-Tranexamic acid, trans-Amcha, Tranhexamic acid

chemical compound used to treat or prevent blood loss

Key facts

Pronunciation: \ˌtran-eks-ˌam-ik-\
Trade names: Cyklokapron, others
Other names: TXA
Ahfs drugs com: Monograph
Medlineplus: a612021
License data: United States"}]]}'>US DailyMed : Tranexamic acid
Pregnancy category: Australia"}]]}'>AU : B1
Routes of administration: By mouth , intravenous , topical
Atc code: B02AA02 ( WHO )
Legal status: Australia"}]]}'>AU : S4 (Prescription only) United Kingdom"}]]}'>UK : POM (Prescription only) / P United States"}]]}'>US : ℞-only Rx generally; OTC (including oral) in Japan
Bioavailability: 34%
Elimination half life: 3.1 h
Cas number: 1197-18-8
Drugbank: DB00302
Unii: 6T84R30KC1
Kegg: D01136
Chebi: CHEBI:48669
Chembl: ChEMBL877

via Wikipedia infobox

Chemical data

Formula: C8H15NO2
Molecular weight: 157.21 g/mol
IUPAC name: 4-(aminomethyl)cyclohexane-1-carboxylic acid
SMILES: C1CC(CCC1CN)C(=O)O
InChIKey: GYDJEQRTZSCIOI-UHFFFAOYSA-N
XLogP: -2
Polar surface area: 63.3 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

9,481 papers

THE USE OF TRANEXAMIC ACID IN DERMATOLOGY.Acta clinica Croatica · 2023
Tranexamic acid: a clinical review.Anaesthesiology intensive therapy · 2015
Efficacy and Safety of Tranexamic Acid in Melasma: A Meta-analysis and Systematic Review.Acta dermato-venereologica · 2017
Tranexamic acid in sinus and nasal surgery: an up-to-date meta-analysis.The Journal of laryngology and otology · 2022
Intra-operative tranexamic acid: A standard of care?Best practice & research. Clinical anaesthesiology · 2023

via PubMed

Wikidata facts

Mass: 157.1103

Show 5 more facts

chemical formula: C₈H₁₅NO₂
World Health Organisation international non-proprietary name: tranexamic acid
isomeric SMILES: C1[C@@H](CC[C@H](C1)C(=O)O)CN
canonical SMILES: C1C(CCC(C1)C(=O)O)CN
Commons category: Tranexamic acid

Sources (3)

via Wikidata · CC0

~10 min read

Article

Tranexamic acid is a medication used to treat or prevent excessive blood loss from major trauma, postpartum bleeding, surgery, tooth removal, nosebleeds, and heavy menstruation. It is also used for hereditary angioedema. It is taken either by mouth, injection into a vein, or by intramuscular injection.

Tranexamic acid is a synthetic analog of the amino acid lysine. It serves as an antifibrinolytic by reversibly binding four to five lysine receptor sites on plasminogen. This decreases the conversion of plasminogen to plasmin, preventing fibrin degradation and preserving the framework of fibrin's matrix structure. Tranexamic acid has roughly eight times the antifibrinolytic activity of an older analogue, ε-aminocaproic acid. Tranexamic acid also directly inhibits the activity of plasmin with weak potency (IC50 = 87 mM), and it can block the active-site of urokinase plasminogen activator (uPA) with high specificity (Ki = 2 mM), one of the highest among all the serine proteases.