Tranexamic acid

Tranexamic acid

Systematic (IUPAC) name
trans-4-(aminomethyl)cyclohexanecarboxylic acid
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pregnancy cat.	B
Legal status	P (UK)
Routes	Injection and oral
Pharmacokinetic data
Bioavailability	34%
Half-life	3.1 h
Identifiers
CAS number	1197-18-8 Y
ATC code	B02AA02
PubChem	CID 5526
DrugBank	APRD01270
ChemSpider	10482000 Y
UNII	6T84R30KC1 Y
KEGG	D01136 Y
ChEBI	CHEBI:48669 Y
ChEMBL	CHEMBL877 Y
Chemical data
Formula	C8H15NO2
Mol. mass	157.21 g/mol
SMILES	eMolecules & PubChem
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- Y Key:GYDJEQRTZSCIOI-LJGSYFOKSA-N Y
N (what is this?)  (verify)

Tranexamic acid (commonly marketed in tablet form as Lysteda and in IV form as Cyklokapron in the U.S. and Australia and as Transamin,Transcam in Asia, and Espercil in South America. Also marketed as Cyclo-F and Femstrual in UK.) is a synthetic derivative of the amino acid lysine. It is used to treat or prevent excessive blood loss during surgery and in various other medical conditions. It is an antifibrinolytic that competitively inhibits the activation of plasminogen to plasmin, by binding to specific sites of both plasminogen and plasmin, a molecule responsible for the degradation of fibrin. Fibrin is a protein that forms the framework of blood clots. It has roughly 8 times the antifibrinolytic activity of an older analogue, ε-aminocaproic acid.

Medical uses

Tranexamic acid is frequently used in surgeries with high risk of blood loss such as cardiac, liver, vascular and large orthopedic procedures. Its oral form is now being evaluated for use in outpatient conditions involving heavy bleeding.

Trauma

Tranexamic acid has been found to decrease the risk of death in people who have significant bleeding due to trauma.

Heart surgery

Tranexamic acid is commonly used in cardiac surgery, both with and without cardiopulmonary bypass. It replaces aprotinin.

Orthopedic surgery

Tranexamic acid is used in orthopedic surgery to reduce bloodloss. It is of proven value in clearing the field of surgery and reducing pre- and postoperative blood loss. Drain and number of transfusions are reduced. However, the hidden blood loss is not reduced. Still, it is becoming an important tool in the anaesthetist's arsenal. It is commonly used in joint replacement surgery.

Menstrual bleeding

Tranexamic acid is a synthetic derivative of the amino acid lysine. It exerts its antifibrinolytic effect through the reversible blockade of lysine-binding sites on plasminogen molecules. It inhibits endometrial (or endothelial^{[citation needed]}) plasminogen activator and thus prevents fibrinolysis and the breakdown of blood clots. Side effects are uncommon. While prolonged treatment may heighten the risk of an increased thrombotic tendency, such as deep vein thrombosis, large scale studies reveal the incidence of thrombosis in women treated by tranexamic acid is no different from the spontaneous incidence of thrombosis in untreated women. Tranexamic acid is used as firstline nonhormonal treatment of dysfunctional uterine bleeding, and heavy bleeding associated with uterine fibroids. A recent study showed patients treated with tranexamic acid are more likely to develop thrombosis and necrosis in their fibroids, and may result in pain and fever. Moreover, the histological appearance of the necrosis in women treated by tranexamic acid is no different from the spontaneous incidence of thrombosis. The U.S. Food and Drug Administration (FDA) approved tranexamic acid oral tablets (brand name Lysteda) for treatment of heavy menstrual bleeding on 13 November 2009.

In March 2011 the status of Tranexamic acid for treatment of heavy menstrual bleeding was changed in the UK, from PoM (Prescription only Medicines) to P (Pharmacy Medicines) and became available over the counter in UK pharmacies under the brand names of Cyclo-F and Femstrual, initially exclusively for Boots pharmacy, which has sparked some discussion about availability. (In parts of Europe - like for example Sweden - it had then been available OTC for over a decade.)

Dentistry

Tranexamic acid is used in dentistry in the form of a 5% mouth rinse after extractions or surgery in patients with prolonged bleeding time, e.g. from acquired or inherited disorders.

Other uses

• In obstetrics, tranexamic acid is used after delivery to reduce bleeding, often with syntocinon/oxytocin and fundal massage. A major trial is in progress worldwide to establish the efficacy of the drug to arrest postpartum haemorrhage (PPH). Since the drug can be administered orally, it has great potential to reduce maternal mortality rates in developing countries where primary healthcare is often unavailable.
• In cardiac surgery, e.g. coronary artery bypass surgery, it is used to prevent excessive blood loss.
• In hemophilia - Tranexamic acid is also useful in the treatment of bleeding as a second line treatment after factor VIII in patients (e.g. tooth extraction).
• In hereditary angioedema

Society and culture

TXA has been included in the WHO list of essential medicines. TXA is inexpensive and treatment would be considered highly cost effective in high, middle and low income countries.

External links

• [1] (PoM to P in the UK)
• [2] (Exclusivity controversy)
• [3] (Final results from the Crash2 study)
• Patient Experience with Tranexamic Acid (Patient Experience)
• Tranexamic acid (Dr. P.L.F. Giangrande, Oxford Haemophilia Centre)
• Tranexamic acid (UK patient information leaflet)
• Effects of tranexamic acid on death, vascular occlusive events, and blood transfusion in trauma patients with significant haemorrhage (CRASH-2): a randomised, placebo-controlled trial (The Lancet)
• Drug will save lives of accident victims, says study (BBC News article)
• Types of Angioedema and treatments (Hereditary Angioedema Association)