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Aminocaproic acid

Chemical compound

Chemical compound

| Drugs.com =

| elimination_half-life = 2 hours

Aminocaproic acid (also known as ε-aminocaproic acid, ε-Ahx, or 6-aminohexanoic acid) is a derivative and analogue of the amino acid lysine, which makes it an effective inhibitor for enzymes that bind that particular residue. Such enzymes include proteolytic enzymes like plasmin, the enzyme responsible for fibrinolysis. For this reason it is effective in treatment of certain bleeding disorders, and it is sold under the brand name Amicar. Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam. The crystal structure determination showed that the 6-aminohexanoic acid is present as a salt, at least in the solid state.

Medical use

Aminocaproic acid (Amicar) is FDA-approved for use in the treatment of acute bleeding due to elevated fibrinolytic activity. It also carries an orphan drug designation from the FDA for the prevention of recurrent hemorrhage in patients with traumatic hyphema. In clinical practice, aminocaproic acid is frequently used off-label for control of bleeding in patients with severe thrombocytopenia, control of oral bleeding in patients with congenital and acquired coagulation disorders, control of perioperative bleeding associated with cardiac surgery, prevention of excessive bleeding in patients on anticoagulation therapy undergoing invasive dental procedures, and reduction of the risk of catastrophic hemorrhage in patients with acute promyelocytic leukemia.

Use in protein biochemistry

In biochemical analyses of membrane proteins, such as BN-PAGE, ε-aminocaproic acid is used to enhance membrane protein solubility while avoiding the addition of sodium chloride.

References

References

  1. G. J. Reiss. (2010). "CSD Communication AMCAPR11: 6-Aminohexanoic acid". [[Cambridge Crystallographic Data Centre]].
  2. (1967). "The crystal structure of ε-aminocaproic acid". [[Acta Crystallographica]].
  3. (9 October 2020). "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet".
  4. (2011). "CCDC 777717: Experimental Crystal Structure Determination". Cambridge Crystallographic Data Centre.
  5. (May 2025). "Aminocaproic acid Orphan Drug Designations and Approvals".
  6. (September 1997). "Topical aminocaproic acid in the treatment of traumatic hyphema". Archives of Ophthalmology.
  7. (September 1989). "Control of bleeding in patients with immune and nonimmune thrombocytopenia with aminocaproic acid". Archives of Internal Medicine.
  8. (February 1981). "Epsilon aminocaproic acid in hemophiliacs undergoing dental extractions: a concise review". Oral Surgery, Oral Medicine, and Oral Pathology.
  9. (1 January 2015). "Epsilon aminocaproic acid reduces blood transfusion and improves the coagulation test after pediatric open-heart surgery: a meta-analysis of 5 clinical trials". International Journal of Clinical and Experimental Pathology.
  10. (1 January 1995). "Antifibrinolytic therapy in cardiac surgery". Texas Heart Institute Journal.
  11. (December 2006). "Hemostatic mouthwashes in anticoagulated patients undergoing dental extraction". The Annals of Pharmacotherapy.
  12. (December 2008). "Acute promyelocytic leukaemia and acquired alpha-2-plasmin inhibitor deficiency: a retrospective look at the use of epsilon-aminocaproic acid (Amicar) in 30 patients". Hematological Oncology.
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