Tranexamic acid

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Tranexamic acid
Tranexamic acid Structural Formulae.png
Tranexamic acid ball-and-stick.png
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 YesY
ATC code B02AA02
PubChem CID 5526
DrugBank DB00302
ChemSpider 10482000 YesY
UNII 6T84R30KC1 YesY
KEGG D01136 YesY
ChEBI CHEBI:48669 YesY
ChEMBL CHEMBL877 YesY
Chemical data
Formula C8H15NO2 
Mol. mass 157.21 g/mol
 YesY (what is this?)  (verify)

Tranexamic acid (\ˌtran-eks-ˌam-ik-\) is a synthetic analog of the amino acid lysine. It is used to treat or prevent excessive blood loss during surgery and in various medical conditions or disorders (helping hemostasis). 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, a protein that forms the framework of blood clots. Tranexamic acid has roughly eight times the antifibrinolytic activity of an older analogue, ε-aminocaproic acid.

Medical uses[edit]

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[edit]

Tranexamic acid has been found to decrease the risk of death in people who have significant bleeding due to trauma.[1][2] However, it may actually increase the risk of death due to bleeding if administered more than 3 hours after the injury.[3]

Heart surgery[edit]

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

Orthopedic surgery[edit]

Tranexamic acid is used in orthopedic surgery to reduce blood loss. 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.

Craniofacial surgery[edit]

Use of tranexamic acid in surgical corrections of craniosynostosis in children reduces the need for blood transfusions.[4]

Menstrual bleeding[edit]

Used as firstline nonhormonal treatment of dysfunctional uterine bleeding, and heavy bleeding associated with uterine fibroids. An August 2007 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.[5] 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 (menorrhagia) was changed in the UK, from PoM (Prescription only Medicines) to P (Pharmacy Medicines)[6] and became available over the counter in UK pharmacies under the brand names of Cyklo-F and Femstrual, initially exclusively for Boots pharmacy, which has sparked some discussion about availability.[7] (In parts of Europe - like Sweden - it had then been available OTC for over a decade.) Regular liver function tests are recommended when using tranexamic acid over a long period of time.[8]

Dentistry[edit]

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[edit]

  • 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[9]
  • In melasma - Tranexamic acid has shown to provide rapid and sustained lightening in melasma by decreasing melanogenesis in epidermal melanocytes.[10]
  • In hyphema - Tranexamic acid has been shown to be effective in reducing risk of secondary hemorrhage outcomes in patients with traumatic hyphema.[11]

Adverse effects[edit]

Rare in general, including gastrointestinal effects, dizziness, fatigue, headache, and hypersensitivity reactions. Use of tranexamic acid has a potential risk of thrombosis.[4]

Society and culture[edit]

TXA has been included in the WHO list of essential medicines.[12] TXA is inexpensive and treatment would be considered highly cost effective in high, middle and low income countries.[13]

Brand names[edit]

Tranexamic acid is marketed in the U.S. and Australia in tablet form as Lysteda and in IV form as Cyklokapron and Transamin, in the UK as Cyclo-F and Femstrual, in Asia as Transcam, in Bangladesh as Traxyl, in South America as Espercil, in Japan as Nicolda, in France and Romania as Exacyl and in Egypt as Kapron.

Synthesis[edit]

Tranexamic acid synthesis:[14] CUATRECASAS LABOR M ES 358367  (1970).

References[edit]

  1. ^ http://www.upmc.com/media/NewsReleases/2014/Pages/pitt-trauma-experts-aim-reduce-deaths-providing-blood-clotting-agent-medical-helicopters.aspx
  2. ^ Cherkas, David (Nov 2011). "Traumatic Hemorrhagic Shock: Advances In Fluid Management". Emergency Medicine Practice 13 (11). 
  3. ^ The CRASH-2 Collaborators (2011). "The importance of early treatment with tranexamic acid in bleeding trauma patients: an exploratory analysis of the CRASH-2 randomised controlled trial". Lancet 377 (9771): 1096–1101, e1–e2. doi:10.1016/S0140-6736(11)60278-X. 
  4. ^ a b RCPCH. "Evidence Statement Major trauma and the use of tranexamic acid in children Nov 2012". Retrieved 17 December 2012. 
  5. ^ Tranexamic acid-associated necrosis and intralesional thrombosis of uterine leiomyomas: a clinicopathologic study of 147 cases emphasizing the importance of drug-induced necrosis and early infarcts in leiomyomas.
  6. ^ Tranexamic Acid to be available OtC
  7. ^ In defence of multiple pharmacies
  8. ^ Tranexamic acid for bleeding from Patient UK. Author: Helen Allen. Last Checked: 13/06/2012
  9. ^ Rod Flower; Humphrey P. Rang; Maureen M. Dale; Ritter, James M. (2007). Rang & Dale's pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5. 
  10. ^ Karn D, KC S, Amatya A, Razouria EA, Timalsina M (October 2010). "Oral Tranexamic Acid for the Treatment of Melasma". Kathmandu University Medical Journal 10 (40): 40–43. 
  11. ^ Gharaibeh A, Savage HI, Scherer RW, Goldberg MF, Lindsley K (2011). "Medical interventions for traumatic hyphema". Cochrane Database Syst Rev 1 (1): CD005431. doi:10.1002/14651858.CD005431.pub2. PMC 3437611. PMID 21249670. 
  12. ^ WHO. Summary of the report of the 18th meeting of the WHO Expert Committee on the Selection and Use of Essential Medicines. 
  13. ^ Guerriero C; Cairns, John; Perel, Pablo; Shakur, Haleema; Roberts, Ian (2011). "Cost-effectiveness analysis of administering tranexamic acid to bleeding trauma patients using evidence from the CRASH-2 trial". In Eltzschig, Holger K. PLoS ONE 6 (5): 18987. Bibcode:2011PLoSO...618987G. doi:10.1371/journal.pone.0018987. 
  14. ^ Levine, M (1959). "Notes. Preparation of p- and m-Aminomethylcyclohexylcarboxylic Acid". The Journal of Organic Chemistry 24 (1): 115–116. doi:10.1021/jo01083a608.  edit

External links[edit]