Tranexamic acid

Last updated

Tranexamic acid
Tranexam.svg
Clinical data
Pronunciation\ˌtran-eks-ˌam-ik-\
Trade names Cyklokapron, others
AHFS/Drugs.com Monograph
MedlinePlus a612021
License data
Routes of
administration 		By mouth, intravenous, topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) [1]
  • UK: POM (Prescription only)/ P
  • US: ℞-only
  • Rx generally; OTC (including oral) in Japan [2]
Pharmacokinetic data
Bioavailability 34%
Elimination half-life 3.1 h
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard 100.013.471 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C8H15NO2
Molar mass 157.213 g·mol−1
3D model (JSmol)
  • NC[C@@H]1CC[C@H](CC1)C(O)=O
  • 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- Yes check.svgY
  • Key:GYDJEQRTZSCIOI-LJGSYFOKSA-N Yes check.svgY
   (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. [3] [4] It is also used for hereditary angioedema. [3] [5] It is taken either orally or by injection into a vein. [3]

Contents

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. [6] Tranexamic acid has roughly eight times the antifibrinolytic activity of an older analogue, ε-aminocaproic acid.[ citation needed ] Tranexamic acid also directly inhibits the activity of plasmin with weak potency (IC50 = 87 mM), [7] 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. [8]

Side effects are rare. [5] Some include changes in color vision, seizures, blood clots, and allergic reactions. [5] Greater caution is recommended in people with kidney disease. [9] Tranexamic acid appears to be safe for use during pregnancy and breastfeeding. [5] [10] Tranexamic acid is an antifibrinolytic medication. [9]

Tranexamic acid was first made in 1962 by Japanese researchers Shosuke and Utako Okamoto. [11] It is on the World Health Organization's List of Essential Medicines. [12] Tranexamic acid is available as a generic drug. [13]

Cosmetic Uses

Tranexamic acid is frequently used in skincare products as a cosmetic active to reduce the appearance of inflammation and hyperpigmentation. TXA is a zwitterion amino acid, and thus has a low permeability coefficient in the stratum corneum [14] . TXA is often combined with penetration enhancers and microneedling to overcome this limitation. [15] Cosmetic uses may also employ lipophilic derivatives of TXA (ester prodrugs) that are not zwitterionic and thus have improved skin permeability. [16] [17] [18]

Medical uses

A one-gram ampoule of tranexamic acid TXAVial2017.jpg
A one-gram ampoule of tranexamic acid

Tranexamic acid is frequently used following major trauma. [19] Tranexamic acid is used to prevent and treat blood loss in a variety of situations, such as dental procedures, heavy menstrual bleeding, and surgeries with high risk of blood loss. [20] [21]

Trauma

Tranexamic acid has been found to decrease the risk of death due to any cause in people who have significant bleeding due to trauma. [22] [23] [24] [25] It is most effective if taken within the first three hours following major trauma. [26] It also decreases the risk of death if given within the first three hours of brain injury. [27]

Menstrual bleeding

Tranexamic acid is sometimes used to treat heavy menstrual bleeding. [21] When taken by mouth it both safely and effectively treats regularly occurring heavy menstrual bleeding and improves quality of life. [6] [28] [29] Another study demonstrated that the dose does not need to be adjusted in females who are between ages 12 and 16. [6] In a 10-year study, tranexamic acid and other oral medicines (mefenamic acid) were as effective as the levonorgestrel intrauterine coil; the same proportion of women had not had surgery for heavy bleeding and had similar improvements in their quality of life. [30] [31]

Childbirth

Tranexamic acid is sometimes used (often in conjunction with oxytocin) to reduce bleeding after childbirth. [32] Death due to postpartum bleeding is reduced in women receiving tranexamic acid. [4]

Surgery

Dentistry

In the United States, tranexamic acid is FDA approved for short-term use in people with severe bleeding disorders who are about to have dental surgery. [39] Tranexamic acid is used for a short period of time before and after the surgery to prevent major blood loss and decrease the need for blood transfusions. [40]

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. [41]

In China, TXA is allowed in over-the-counter toothpastes, with six products using the drug. As of 2018, there are no limits on dosage, nor requirements for labeling the concentration. [42] 0.05% TXA in toothpaste is allowed OTC in Hong Kong. [43] <5% TXA in over-the-counter toothpaste is first patented and marketed by Lion Corporation in Japan, [44] where it is still sold. [45] Presence of unauthorized TXA has led to the Canadian recall of a Yunnan Baiyao toothpaste in 2019. [46]

Hematology

There is not enough evidence to support the routine use of tranexamic acid to prevent bleeding in people with blood cancers. [47] However, there are several trials that are currently assessing this use of tranexamic acid. [47] For people with inherited bleeding disorders (e.g. von Willebrand's disease), tranexamic acid is often given. [48] It has also been recommended for people with acquired bleeding disorders (e.g., directly acting oral anticoagulants (DOACs)) to treat serious bleeding. [49]

Nosebleeds

The use of tranexamic acid, applied directly to the area that is bleeding or taken by mouth, appears useful to treat nose bleeding compared to packing the nose with cotton pledgets alone. [50] [51] [52] It decreases the risk of rebleeding within 10 days. [53]

Other uses

Experimental uses

Tranexamic acid might alleviate neuroinflammation in some experimental settings. [62]

Tranexamic acid can be used in case of postpartum hemorrhage; it can decrease the risk of death due to bleeding by one third according to the WHO. [63]

Contraindications

Adverse effects

Side effects are rare. [5] Some reported adverse events include seizures, changes in color vision, blood clots, and allergic reactions such as anaphylaxis. [5] Whether the risk of venous thromboembolism (blood clots) is actually increased is a matter of debate. The risk is mentioned in the product literature, [6] and they were reported in post marketing experience. [6] Despite this, and the inhibitory effect of tranexamic acid on blood clot breakdown, large studies of the use of tranexamic acid have not shown an increase in the risk of venous or arterial thrombosis, [64] [65] even in people who had previously experienced thrombosis under other circumstances. [65]

Special populations

Society and culture

Tranexamic acid was first synthesized in 1962 by Japanese researchers Shosuke and Utako Okamoto. [11] It has been included in the WHO list of essential medicines. [67]

Brand names

Tranexamic acid is marketed in the U.S. and Australia in tablet form as Lysteda and in Australia, Sweden [68] and Jordan it is marketed in an IV form and tablet form as Cyklokapron, in the UK and Sweden [68] as Cyclo-F. In the UK it is also marketed as Femstrual, in Asia as Transcam, in Bangladesh as Intrax & Tracid, in India as Pause, in Pakistan as Transamin, in South America as Espercil, in Japan as Nicolda, in France, Poland, Belgium and Romania as Exacyl and in Egypt as Kapron. In the Philippines, its capsule form is marketed as Hemostan and in Israel as Hexakapron.[ citation needed ]

The U.S. Food and Drug Administration (FDA) approved tranexamic acid oral tablets (brand name Lysteda) for treatment of heavy menstrual bleeding in November 2009. [69]

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) [70] 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; [71] in parts of Europe it had then been available OTC for over a decade. [69] Regular liver function tests are recommended when using tranexamic acid over a long period of time. [72]

Related Research Articles

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<span class="mw-page-title-main">Dysmenorrhea</span> Pain during and sometimes before menstruation

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<span class="mw-page-title-main">Upper gastrointestinal bleeding</span> Medical condition

Upper gastrointestinal bleeding is gastrointestinal bleeding (hemorrhage) in the upper gastrointestinal tract, commonly defined as bleeding arising from the esophagus, stomach, or duodenum. Blood may be observed in vomit or in altered form as black stool. Depending on the amount of the blood loss, symptoms may include shock.

<span class="mw-page-title-main">Nosebleed</span> Bleeding from the nose

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The fibrinolysis system is responsible for removing blood clots. Hyperfibrinolysis describes a situation with markedly enhanced fibrinolytic activity, resulting in increased, sometimes catastrophic bleeding. Hyperfibrinolysis can be caused by acquired or congenital reasons. Among the congenital conditions for hyperfibrinolysis, deficiency of alpha-2-antiplasmin or plasminogen activator inhibitor type 1 (PAI-1) are very rare. The affected individuals show a hemophilia-like bleeding phenotype. Acquired hyperfibrinolysis is found in liver disease, in patients with severe trauma, during major surgical procedures, and other conditions. A special situation with temporarily enhanced fibrinolysis is thrombolytic therapy with drugs which activate plasminogen, e.g. for use in acute ischemic events or in patients with stroke. In patients with severe trauma, hyperfibrinolysis is associated with poor outcome. Moreover, hyperfibrinolysis may be associated with blood brain barrier impairment, a plasmin-dependent effect due to an increased generation of bradykinin.

Haleema Shakur-Still is a professor of Global Health Clinical Trials and the co-director of London School of Hygiene & Tropical Medicine's Clinical Trials Unit.

References

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  38. ↑ Pernik MN, Dosselman LJ, Aoun SG, Walker AD, Hall K, Peinado Reyes V, et al. (2020). "The effectiveness of tranexamic acid on operative and perioperative blood loss in long-segment spinal fusions: a consecutive series of 119 primary procedures". Journal of Neurosurgery. Spine. 32 (5): 768–774. doi: 10.3171/2019.11.SPINE191174 . PMID   31978874.
  39. ↑ "Cyklokapron (tranexamic acid) Product Information" (PDF). Archived from the original (PDF) on 29 February 2016. Retrieved 3 November 2015.
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