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 names	Amicar
AHFS/Drugs.com	Monograph
MedlinePlus	a608023
License data	US DailyMed: Aminocaproic_acid
Routes of administration	By mouth
ATC code	B02AA01 (WHO)
Legal status
Legal status	US: ℞-only[3] In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Kidney
Elimination half-life	2 hours
Identifiers
IUPAC name 6-aminohexanoic acid
CAS Number	60-32-2 Y
PubChem CID	564
IUPHAR/BPS	6574
DrugBank	DB00513 Y
ChemSpider	548 Y
UNII	U6F3787206
KEGG	D00160 Y
ChEBI	CHEBI:16586 Y
ChEMBL	ChEMBL1046 Y
NIAID ChemDB	018631
CompTox Dashboard (EPA)	DTXSID0020070
ECHA InfoCard	100.000.427
Chemical and physical data
Formula	C6H13NO2
Molar mass	131.175 g·mol−1
3D model (JSmol)	Interactive image
Melting point	205 °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
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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][6] In clinical practice, aminocaproic acid is frequently used off-label for control of bleeding in patients with severe thrombocytopenia,^[7] control of oral bleeding in patients with congenital and acquired coagulation disorders,^[8] control of perioperative bleeding associated with cardiac surgery,^[9][10] prevention of excessive bleeding in patients on anticoagulation therapy undergoing invasive dental procedures,^[11] and reduction of the risk of catastrophic hemorrhage in patients with acute promyelocytic leukemia.^[12]

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 18 August 2021.
2. Bodor G, Bednowitz AL, Post B (1967). "The crystal structure of ε-aminocaproic acid". Acta Crystallographica. 23 (3): 482–490. Bibcode:1967AcCry..23..482B. doi:10.1107/S0365110X67003019.
3. "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet". DailyMed. 9 October 2020. Retrieved 11 November 2020.
4. Reiss GJ (2011), "Crystal Structure", CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre, doi:10.5517/ccv38nv, retrieved 24 October 2019
5. "Aminocaproic acid Orphan Drug Designations and Approvals". U.S. Food and Drug Administration (FDA). 6 January 1995. Retrieved 11 November 2020.
6. Crouch Jr ER, Williams PB, Gray MK, Chames M (September 1997). "Topical aminocaproic acid in the treatment of traumatic hyphema". Archives of Ophthalmology. 115 (9): 1106–1112. doi:10.1001/archopht.1997.01100160276001. PMID 9298049.
7. Bartholomew JR, Salgia R, Bell WR (September 1989). "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. PMID 2774776.
8. Lucas ON, Albert TW (February 1981). "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. PMID 6782532.
9. Lu J, Meng H, Meng Z, Sun Y, Pribis JP, Zhu C, Li Q (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. 8 (7): 7978–7987. PMC 4555692. PMID 26339364.
10. Chen RH, Frazier OH, Cooley DA (1 January 1995). "Antifibrinolytic therapy in cardiac surgery". Texas Heart Institute Journal. 22 (3): 211–215. PMC 325256. PMID 7580358.
11. Patatanian E, Fugate SE (December 2006). "Hemostatic mouthwashes in anticoagulated patients undergoing dental extraction". The Annals of Pharmacotherapy. 40 (12): 2205–2210. doi:10.1345/aph.1H295. PMID 17090725. S2CID 33961815.
12. Wassenaar T, Black J, Kahl B, Schwartz B, Longo W, Mosher D, Williams E (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. 26 (4): 241–246. doi:10.1002/hon.867. PMC 3496178. PMID 18613223.

Further reading

• Alkjaersig N, Fletcher AP, Sherry S (April 1959). "xi-Aminocaproic acid: an inhibitor of plasminogen activation". The Journal of Biological Chemistry. 234 (4): 832–837. doi:10.1016/S0021-9258(18)70185-3. PMID 13654273.
• Kang Y, Lewis JH, Navalgund A, Russell MW, Bontempo FA, Niren LS, Starzl TE (June 1987). "Epsilon-aminocaproic acid for treatment of fibrinolysis during liver transplantation". Anesthesiology. 66 (6): 766–773. doi:10.1097/00000542-198706000-00010. PMC 2965586. PMID 3296855.