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Tranexamic acid information


Tranexamic acid
Clinical data
Pronunciation\ˌtran-eks-ˌam-ik-\
Trade namesCyklokapron, others
Other namesTXA
AHFS/Drugs.comMonograph
MedlinePlusa612021
License data
  • US DailyMed: Tranexamic acid
Routes of
administration
By mouth, intravenous, topical
ATC code
  • B02AA02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[1]
  • UK: POM (Prescription only) / P[2][3]
  • US: ℞-only[4]
  • Rx generally; OTC (including oral) in Japan[5]
Pharmacokinetic data
Bioavailability34%
Elimination half-life3.1 h
Identifiers
IUPAC name
  • trans-4-(aminomethyl)cyclohexanecarboxylic acid
CAS Number
  • 1197-18-8 checkY
PubChem CID
  • 5526
IUPHAR/BPS
  • 6573
DrugBank
  • DB00302 checkY
ChemSpider
  • 10482000 checkY
UNII
  • 6T84R30KC1
KEGG
  • D01136 checkY
ChEBI
  • CHEBI:48669 checkY
ChEMBL
  • ChEMBL877 checkY
PDB ligand
  • AMH (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID3045350 Edit this at Wikidata
ECHA InfoCard100.013.471 Edit this at Wikidata
Chemical and physical data
FormulaC8H15NO2
Molar mass157.213 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- checkY
  • Key:GYDJEQRTZSCIOI-LJGSYFOKSA-N checkY
  (verify)

Tranexamic acid is a medication used to treat or prevent excessive blood loss from major trauma, postpartum bleeding, surgery, tooth removal, nosebleeds, and heavy menstruation.[6][7] It is also used for hereditary angioedema.[6][2] It is taken either by mouth]] or by injection into a vein.[6]

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.[4] 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),[8] 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.[9]

Side effects are rare.[2] Some include changes in color vision, seizures, blood clots, and allergic reactions.[2] Tranexamic acid appears to be safe for use during pregnancy and breastfeeding.[2][10] Tranexamic acid is an antifibrinolytic medication.[11]

Tranexamic acid was first made in 1962 by Japanese researchers Shosuke and Utako Okamoto.[12] It is on the World Health Organization's List of Essential Medicines.[13] Tranexamic acid is available as a generic drug.[14]

  1. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
  2. ^ a b c d e "Cyklokapron Tablets - Summary of Product Characteristics (SPC) - (eMC)". emc. September 2016. Archived from the original on 20 December 2016. Retrieved 14 December 2016.
  3. ^ "Evana Heavy Period Relief Summary of Product Characteristics (SmPC)". (emc). 24 April 2024. Retrieved 14 May 2024.
  4. ^ a b Cite error: The named reference Lysteda FDA label was invoked but never defined (see the help page).
  5. ^ 会議事録 [Minutes of the meeting]. 薬事・食品衛生審議会一般用医薬品部会 (in Japanese). 22 March 2007. Archived from the original on 7 September 2022. Retrieved 7 September 2022.
  6. ^ a b c British national formulary: BNF 69 (69 ed.). British Medical Association. 2015. p. 170. ISBN 978-0-85711-156-2.
  7. ^ Shakur H, Roberts I, Fawole B, Chaudhri R, El-Sheikh M, Akintan A, et al. (WOMAN Trial Collaborators) (2017). "Effect of early tranexamic acid administration on mortality, hysterectomy, and other morbidities in women with post-partum haemorrhage (WOMAN): an international, randomised, double-blind, placebo-controlled trial". Lancet. 389 (10084): 2105–2116. doi:10.1016/S0140-6736(17)30638-4. PMC 5446563. PMID 28456509.
  8. ^ Law RH, Wu G, Leung EW, Hidaka K, Quek AJ, Caradoc-Davies TT, et al. (2017). "X-ray crystal structure of plasmin with tranexamic acid-derived active site inhibitors". Blood Advances. 1 (12): 766–771. doi:10.1182/bloodadvances.2016004150. PMC 5728053. PMID 29296720.
  9. ^ Wu G, Mazzitelli BA, Quek AJ, Veldman MJ, Conroy PJ, Caradoc-Davies TT, et al. (2019). "Tranexamic acid is an active site inhibitor of urokinase plasminogen activator". Blood Advances. 3 (5): 729–733. doi:10.1182/bloodadvances.2018025429. PMC 6418500. PMID 30814058.
  10. ^ "Tranexamic acid Use During Pregnancy". Drugs.com. Archived from the original on 21 December 2016. Retrieved 14 December 2016.
  11. ^ "Tranexamic Acid Injection - FDA prescribing information, side effects and uses". Drugs.com. Archived from the original on 21 December 2016. Retrieved 14 December 2016.
  12. ^ Watts G (2016). "Utako Okamoto". Lancet. 387 (10035): 2286. doi:10.1016/S0140-6736(16)30697-3. PMID 27308678.
  13. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  14. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 415. ISBN 978-1-284-05756-0.

and 29 Related for: Tranexamic acid information

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Tranexamic acid

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Tranexamic acid is a medication used to treat or prevent excessive blood loss from major trauma, postpartum bleeding, surgery, tooth removal, nosebleeds...

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Nosebleed

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of the nose. If this is not sufficient, nasal packing may be used. Tranexamic acid may also be helpful. If bleeding episodes continue, endoscopy is recommended...

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Mouthwash

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of recurrent aphthous stomatitis. Erythromycin is similar. A 4.8% tranexamic acid solution is sometimes used as an antifibrinolytic mouthwash to prevent...

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Hemoptysis

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saline, and topical vasoconstrictors such as adrenaline or vasopressin. Tranexamic acid was proved to improve in-hospital mortality. Selective bronchial intubation...

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Melasma

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risk of harm to the fetus. Azelaic acid (20%) is thought to decrease the activity of melanocytes. Tranexamic acid by mouth has shown to provide rapid...

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Coagulopathy

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concentrate, factor XIII, and fibrinogen Fibrinogen with tranexamic acid The use of tranexamic acid is the only option that is currently supported by a large...

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GABA receptor antagonist

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Heinz Redl (April 2002). "Tranexamic Acid, a Widely Used Antifibrinolytic Agent, Causes Convulsions by a γ-Aminobutyric AcidA Receptor Antagonistic Effect"...

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Postpartum bleeding

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garment to help until other measures such as surgery can be carried out. Tranexamic acid has also been shown to reduce the risk of death, and has been recommended...

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Antifibrinolytic

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inhibitors of fibrinolysis. Examples include aminocaproic acid (ε-aminocaproic acid) and tranexamic acid. These lysine-like drugs interfere with the formation...

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Mefenamic acid

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prescribed for menorrhagia. In a 10-year study, mefenamic acid and other oral medicines (tranexamic acid) were as effective as the levonorgestrel intrauterine...

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Hypovolemic shock

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elective surgery. The CRASH-2 study was a randomized control trial of tranexamic acid versus placebo in trauma has been shown to decrease overall mortality...

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Heavy menstrual bleeding

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quality of life. Initial treatment often involve birth control pills. Tranexamic acid, danazol, progesterone IUDs, and NSAIDs are also helpful. Surgery can...

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Utako Okamoto

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Japanese medical doctor working as a medical scientist who discovered tranexamic acid in the 1950s in her quest to find a drug that would treat bleeding...

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Upper gastrointestinal bleeding

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stopped by various techniques. Proton pump inhibitors are often used. Tranexamic acid may also be useful. Procedures (such as TIPS for variceal bleeding)...

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Cyclohexanecarboxylic acid

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cyclohexanecarboxylic acid include: abscisic acid buciclic acid chlorogenic acid chorismic acid dicyclomine quinic acid shikimic acid tranexamic acid Quinic acid Shikimic...

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Major trauma

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products are only available for general use in South Africa and Russia. Tranexamic acid decreases death in people who are having ongoing bleeding due to trauma...

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Aprotinin

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compared to other antifibrinolytic drugs (epsilon-aminocaproic acid and tranexamic acid) aprotinin may increase the risk of death. On October 29, 2006...

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Abnormal uterine bleeding

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hormonal birth control, gonadotropin-releasing hormone (GnRH) agonists, tranexamic acid, NSAIDs, and surgery such as endometrial ablation or hysterectomy....

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Angiodysplasia

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necessary. First-line options include the antifibrinolytics tranexamic acid or aminocaproic acid. Estrogens can be used to stop bleeding from angiodysplasia...

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Hereditary hemorrhagic telangiectasia

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moist, and by applying saline solution, estrogen-containing creams or tranexamic acid; these have few side effects and may have a small degree of benefit...

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Haemophilia C

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mixing study.[citation needed] In terms of haemophilia C medication tranexamic acid is often used for both treatment after an incident of bleeding and...

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Thromboelastography

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fibrinolysis and may be treated with an antifibrinolytic, such as tranexamic acid or aminocaproic acid, in the appropriate clinical setting. A single, modified...

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Uterine myomectomy

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mesna), vaginal insertion of dinoprostone, a gelatin–thrombin matrix, tranexamic acid, infusion of vitamin C, infiltration of a mixture of bupivacaine and...

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WHO Model List of Essential Medicines

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Dabigatran Enoxaparin Heparin sodium Phytomenadione Protamine sulfate Tranexamic acid Warfarin Complementary: Desmopressinα Heparin sodiumα Protamine sulfateα...

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Uremia

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be used routinely. To reduce bleeding during and after a procedure, tranexamic acid, both as a rinse or administered orally, can be used. Patients undergoing...

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Greyhound

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prevented and treated by administering antifibrinolytic medication such as tranexamic acid via the oral or parenteral route. Intensive care and blood product...

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Gastrointestinal bleeding

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immediate clinical importance. There is tentative evidence of benefit for tranexamic acid which inhibits clot breakdown. Somatostatin and octreotide, while recommended...

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Skin whitening

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of benefit of tranexamic acid in melasma, while another 2017 review found that evidence to support its use was insufficient. Azelaic acid may be a second-line...

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Angioedema

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nonhistaminergic angioedema, antifibrinolytics such as tranexamic acid or ε-aminocaproic acid may be effective. Cinnarizine may also be useful because...

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