Tranexamic acid

Tranexamic acid
Clinical data
Pronunciation	\ˌtran-eks-ˌam-ik-\
Trade names	Cyklokapron, others
AHFS/Drugs.com	Monograph
MedlinePlus	a612021
License data	US DailyMed: Tranexamic acid;
Routes of; administration	By mouth, intravenous, topical
ATC code	B02AA02 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only) / P; US: ℞-only; Rx generally; OTC (including oral) in Japan;
Pharmacokinetic data
Bioavailability	34%
Elimination half-life	3.1 h
Identifiers
	IUPAC name trans-4-(aminomethyl)cyclohexanecarboxylic acid;
CAS Number	1197-18-8 ;
PubChem CID	5526;
IUPHAR/BPS	6573;
DrugBank	DB00302 ;
ChemSpider	10482000 ;
UNII	6T84R30KC1;
KEGG	D01136 ;
ChEBI	CHEBI:48669 ;
ChEMBL	ChEMBL877 ;
PDB ligand	AMH (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3045350 ;
ECHA InfoCard	100.013.471
Chemical and physical data
Formula	C8H15NO2
Molar mass	157.213 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES NC[C@@H]1CC[C@H](CC1)C(O)=O;
	InChI 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- ; Key:GYDJEQRTZSCIOI-LJGSYFOKSA-N ;
	(verify)

Tranexamic acid (TXA) 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 orally or by injection into a vein.

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.

Side effects are rare. Some include changes in color vision, seizures, blood clots, and allergic reactions. Greater caution is recommended in people with kidney disease. Tranexamic acid appears to be safe for use during pregnancy and breastfeeding. Tranexamic acid is an antifibrinolytic medication.

Tranexamic acid was first made in 1962 by Japanese researchers Shosuke and Utako Okamoto. It is on the World Health Organization's List of Essential Medicines. Tranexamic acid is available as a generic drug.

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