Aminocaproic acid

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Aminocaproic acid
6-Aminocaproic acid.png
Aminocaproic-acid-from-xtal-3D-bs-17.png
Ball-and-stick model of the zwitterionic form of the molecule found in the crystal structure[1][2]
Names
Trade namesAmicar
Other namesε-aminocaproic acid, ε-Ahx
  • 6-aminohexanoic acid
Clinical data
Main usesCertain bleeding disorders[3]
Side effectsNausea, abdominal pain, diarrhea, dizziness, fever, shortness of breath, headache, swelling, itchiness[4]
Pregnancy
category
  • US: C (Risk not ruled out)[5]
Routes of
use
By mouth, intravenous
External links
AHFS/Drugs.comMonograph
US NLMAminocaproic acid
MedlinePlusa608023
Legal
License data
Legal status
Pharmacokinetics
MetabolismKidney
Elimination half-life2 hours
Chemical and physical data
FormulaC6H13NO2
Molar mass131.175 g·mol−1
3D model (JSmol)
Melting point205 °C (401 °F)
  • C(CCC(=O)O)CCN
  • InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9) checkY
  • Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N checkY
  (verify)

Aminocaproic acid, sold under the brand name Amicar among others, is a medication used to treat certain bleeding disorders.[3] This may include bleeding due to fibrinolysis such as may occur following heart surgery, abruptio placentae, liver cirrhosis, and in cancer; bleeding within the eye; and hereditary hemorrhagic telangiectasia.[3][4] It may be taken by mouth or injection into a vein.[4]

Common side effects include nausea, abdominal pain, diarrhea, dizziness, fever, shortness of breath, headache, swelling, and itchiness.[4] Other side effects may include muscle breakdown.[4] It should generally not be used in people with bleeding from within the kidney.[4] Safety in pregnancy is unclear.[4] It is a form of carboxylic acid that decreases fibrinolysis.[4]

Aminocaproic acid was approved for medical use in the United States in 1964.[4] It is available as a generic medication.[6] In the United States 15 pills of 500 mg costs about 44 USD as of 2022.[6]

Medical use

Aminocaproic acid is used to treat 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.[7] In clinical practice, aminocaproic acid is frequently used off-label for control of bleeding in patients with severe thrombocytopenia,[8] control of oral bleeding in patients with congenital and acquired coagulation disorders,[9] control of perioperative bleeding associated with cardiac surgery,[10][11] prevention of excessive bleeding in patients on anticoagulation therapy undergoing invasive dental procedures,[12] and reduction of the risk of catastrophic hemorrhage in patients with acute promyelocytic leukemia.[13]

Society and culture

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.[14]

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. 3.0 3.1 3.2 3.3 3.4 "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet". DailyMed. 9 October 2020. Retrieved 11 November 2020.
  4. 4.0 4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.8 "Aminocaproic Acid Monograph for Professionals". Drugs.com. Retrieved 14 January 2022.
  5. "Aminocaproic acid (Amicar) Use During Pregnancy". Drugs.com. 29 April 2020. Retrieved 11 November 2020.
  6. 6.0 6.1 "Aminocaproic Acid Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 14 January 2022.
  7. "Aminocaproic acid Orphan Drug Designations and Approvals". U.S. Food and Drug Administration (FDA). 6 January 1995. Retrieved 11 November 2020.
  8. 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.
  9. 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.
  10. 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.
  11. 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.
  12. 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.
  13. 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.
  14. Reiss, G.J. (2011), "Crystal Structure", CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre, doi:10.5517/ccv38nv, retrieved 2019-10-24

External links

Identifiers: