trans-Tranexamic acid
[CAS# 1197-18-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: trans-Tranexamic acid
• Synonyms: trans-4-Aminomethylcyclohexane-1-carboxylate; trans-4-(Aminomethyl)cyclohexanecarboxylic acid; Amstat
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.21
• CAS Registry Number: 1197-18-8
• EC Number: 214-818-2
• SMILES: C1[C@@H](CC[C@H](C1)C(=O)O)CN

Properties

• Solubility: Soluble (42 g/L) (25 °C), Calc.^*
• Density: 1.095±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: > 300 °C ^**
• Boiling point: 300.2±15.0 °C (760 Torr), Calc.^*
• Flash point: 135.4±20.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

^** )Misra, Arvind

Safety Data

• Hazard Symbols: Xi
• Risk Statements: R36/37/38
• Safety Statements: S26;S37/39

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Carcinogenicity	Carc.	2	H351
Reproductive toxicity	Lact.	-	H362

Discovery and Applications

Trans-tranexamic acid, commonly known as tranexamic acid (TXA), is a synthetic derivative of the amino acid lysine. It was first discovered in the 1950s by Japanese researchers who were studying the role of amino acids in blood clotting. Tranexamic acid was originally developed as an antifibrinolytic agent because of its ability to inhibit the breakdown of blood clots. Its molecular structure consists of the trans-4-aminomethylcyclohexanecarboxylic acid moiety.

One of the main applications of tranexamic acid is to control bleeding. It acts by competitively inhibiting the activation of plasminogen to plasmin, an enzyme responsible for fibrinolysis and thrombolysis. By preventing the breakdown of fibrin clots, tranexamic acid promotes hemostasis and helps control bleeding in a variety of clinical settings. Tranexamic acid is widely used in surgical and trauma settings to reduce blood loss and the need for transfusions. It is administered intravenously or topically during surgical procedures, particularly in orthopedic, cardiovascular, and trauma procedures, to minimize intraoperative and postoperative bleeding. Tranexamic acid is also used to treat menstrual disorders characterized by heavy menstrual bleeding, such as menorrhagia and dysfunctional uterine bleeding. Oral tranexamic acid taken during menstruation helps reduce menstrual flow by inhibiting endometrial fibrinolysis and stabilizing thrombi in the uterine cavity. Tranexamic acid is used in dentistry and oral surgery for its hemostatic properties. It is used as a mouthwash or topical hemostatic agent to control bleeding after tooth extractions, periodontal surgery, and oral mucosal surgery. In addition to preventing and controlling surgical bleeding, tranexamic acid is used to treat a variety of bleeding disorders, including hemophilia, von Willebrand's disease, and thrombocytopenia. It may be used as an adjunct to conventional treatments, such as factor replacement therapy and platelet transfusion, to promote thrombostabilization and reduce the severity and duration of bleeding events in patients with bleeding disorders. Tranexamic acid is popular in cosmetic dermatology for its skin lightening and depigmentation effects. It inhibits melanin synthesis and reduces hyperpigmentation by interfering with melanogenesis pathways and inhibiting melanocyte activity. Topical preparations containing tranexamic acid are used to treat a variety of pigmentary disorders, including melasma, post-inflammatory hyperpigmentation, and solar freckles.

References

1987. Tranexamic Acid in Gastric and Duodenal Bleeding. Scandinavian Journal of Gastroenterology. Supplement.
DOI: 10.3109/00365528709089767

2000. Tranexamic Acid Reduces Blood Loss in Total Hip Replacement Surgery. Anesthesia and Analgesia.
DOI: 10.1097/00000539-200011000-00014

2024. Topische Tranexamsäure hilft bei Nasenbluten. CME.
DOI: 10.1007/s11298-024-4113-3