Chemistry:Aminocaproic acid
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| Trade names | Amicar |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a608023 |
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| Routes of administration | By mouth |
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| Metabolism | Kidney |
| Elimination half-life | 2 hours |
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| Formula | C6H13NO2 |
| Molar mass | 131.175 g·mol−1 |
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| Melting point | 205 °C (401 °F) |
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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.[4] 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.[5]
Medical use
Aminocaproic acid (Amicar) is FDA-approved for use in the treatment of acute bleeding due to elevated fibrinolytic activity.[4] It also carries an orphan drug designation from the FDA for the prevention of recurrent hemorrhage in patients with traumatic hyphema.[6][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]
References
- ↑ G. J. Reiss (2010). CSD Communication AMCAPR11: 6-Aminohexanoic acid. Cambridge Crystallographic Data Centre. doi:10.5517/ccv38nv. https://dx.doi.org/10.5517/ccv38nv. Retrieved 2021-08-18.
- ↑ "The crystal structure of ε-aminocaproic acid". Acta Crystallographica 23 (3): 482–490. 1967. doi:10.1107/S0365110X67003019.
- ↑ "Aminocaproic acid (Amicar) Use During Pregnancy". 29 April 2020. https://www.drugs.com/pregnancy/aminocaproic-acid.html.
- ↑ 4.0 4.1 4.2 "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet". 9 October 2020. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2238c70f-b0b5-4755-896b-45b28777b217.
- ↑ "Crystal Structure", CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre, 2011, doi:10.5517/ccv38nv, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccv38nv&sid=DataCite, retrieved 2019-10-24
- ↑ "Aminocaproic acid Orphan Drug Designations and Approvals". 6 January 1995. https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=83294.
- ↑ "Topical aminocaproic acid in the treatment of traumatic hyphema". Archives of Ophthalmology 115 (9): 1106–1112. September 1997. doi:10.1001/archopht.1997.01100160276001. PMID 9298049.
- ↑ "Control of bleeding in patients with immune and nonimmune thrombocytopenia with aminocaproic acid". Archives of Internal Medicine 149 (9): 1959–1961. September 1989. doi:10.1001/archinte.1989.00390090039008. PMID 2774776.
- ↑ "Epsilon aminocaproic acid in hemophiliacs undergoing dental extractions: a concise review". Oral Surgery, Oral Medicine, and Oral Pathology 51 (2): 115–120. February 1981. doi:10.1016/0030-4220(81)90025-6. PMID 6782532.
- ↑ "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. 2015-01-01. PMID 26339364.
- ↑ "Antifibrinolytic therapy in cardiac surgery". Texas Heart Institute Journal 22 (3): 211–215. 1995-01-01. PMID 7580358.
- ↑ "Hemostatic mouthwashes in anticoagulated patients undergoing dental extraction". The Annals of Pharmacotherapy 40 (12): 2205–2210. December 2006. doi:10.1345/aph.1H295. PMID 17090725.
- ↑ "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 26 (4): 241–246. December 2008. doi:10.1002/hon.867. PMID 18613223.
Further reading
- "xi-Aminocaproic acid: an inhibitor of plasminogen activation". The Journal of Biological Chemistry 234 (4): 832–837. April 1959. doi:10.1016/S0021-9258(18)70185-3. PMID 13654273.
- "Epsilon-aminocaproic acid for treatment of fibrinolysis during liver transplantation". Anesthesiology 66 (6): 766–773. June 1987. doi:10.1097/00000542-198706000-00010. PMID 3296855.
External links
- "Aminocaproic acid". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/aminocaproic%20acid.
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