Aminocaproic acid

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.[3] 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.[4]

Aminocaproic acid
Skeletal formula
Ball-and-stick model of the zwitterionic form of the molecule found in the crystal structure[1][2]
Clinical data
Trade namesAmicar
AHFS/Drugs.comMonograph
MedlinePlusa608023
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismKidney
Elimination half-life2 hours
Identifiers
IUPAC name
  • 6-aminohexanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.427
Chemical and physical data
FormulaC6H13NO2
Molar mass131.175 g·mol−1
3D model (JSmol)
Melting point205 °C (401 °F)
SMILES
  • C(CCC(=O)O)CCN
InChI
  • InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9) Y
  • Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N Y
  (verify)

Medical use

Aminocaproic acid (Amicar) is FDA-approved for use in the treatment of acute bleeding due to elevated fibrinolytic activity.[3] It also carries an orphan drug designation from the FDA for the prevention of recurrent hemorrhage in patients with traumatic hyphema.[5] In clinical practice, aminocaproic acid is frequently used off-label for control of bleeding in patients with severe thrombocytopenia,[6] control of oral bleeding in patients with congenital and acquired coagulation disorders,[7] control of perioperative bleeding associated with cardiac surgery,[8][9] prevention of excessive bleeding in patients on anticoagulation therapy undergoing invasive dental procedures,[10] and reduction of the risk of catastrophic hemorrhage in patients with acute promyelocytic leukemia.[11]

References
  1. G. J. Reiss (2010). "CSD Communication AMCAPR11: 6-Aminohexanoic acid". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/ccv38nv. Retrieved 2021-08-18.
  2. Bodor, Géza; Bednowitz, Allan L.; Post, Ben (1967). "The crystal structure of ε-aminocaproic acid". Acta Crystallographica. 23 (3): 482–490. doi:10.1107/S0365110X67003019.
  3. "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet". DailyMed. 9 October 2020. Retrieved 11 November 2020.
  4. Reiss, G.J. (2011), "Crystal Structure", CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre, doi:10.5517/ccv38nv, retrieved 2019-10-24
  5. "Aminocaproic acid Orphan Drug Designations and Approvals". U.S. Food and Drug Administration (FDA). 6 January 1995. Retrieved 11 November 2020.
  6. Bartholomew JR; Salgia R; Bell WR (1989-09-01). "Control of bleeding in patients with immune and nonimmune thrombocytopenia with aminocaproic acid". Archives of Internal Medicine. 149 (9): 1959–1961. doi:10.1001/archinte.1989.00390090039008. ISSN 0003-9926. PMID 2774776.
  7. Lucas, O. N.; Albert, T. W. (1981-02-01). "Epsilon aminocaproic acid in hemophiliacs undergoing dental extractions: a concise review". Oral Surgery, Oral Medicine, and Oral Pathology. 51 (2): 115–120. doi:10.1016/0030-4220(81)90025-6. ISSN 0030-4220. PMID 6782532.
  8. Lu, Jun; Meng, Haoyu; Meng, Zhaoyi; Sun, Ying; Pribis, John P.; Zhu, Chunyan; Li, Quan (2015-01-01). "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. 8 (7): 7978–7987. ISSN 1936-2625. PMC 4555692. PMID 26339364.
  9. Chen, R. H.; Frazier, O. H.; Cooley, D. A. (1995-01-01). "Antifibrinolytic therapy in cardiac surgery". Texas Heart Institute Journal. 22 (3): 211–215. ISSN 0730-2347. PMC 325256. PMID 7580358.
  10. Patatanian, Edna; Fugate, Susan E. (2006-12-01). "Hemostatic mouthwashes in anticoagulated patients undergoing dental extraction". The Annals of Pharmacotherapy. 40 (12): 2205–2210. doi:10.1345/aph.1H295. ISSN 1542-6270. PMID 17090725. S2CID 33961815.
  11. Wassenaar, T.; Black, J.; Kahl, B.; Schwartz, B.; Longo, W.; Mosher, D.; Williams, E. (2008-12-01). "Acute promyelocytic leukaemia and acquired α-2-plasmin inhibitor deficiency: a retrospective look at the use of epsilon-aminocaproic acid (Amicar) in 30 patients". Hematological Oncology. 26 (4): 241–246. doi:10.1002/hon.867. ISSN 1099-1069. PMC 3496178. PMID 18613223.

Further reading
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