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Aminocaproic acid

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Chemical compound
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Pharmaceutical compound
Aminocaproic acid
Ball-and-stick model of thezwitterionic form of the molecule found in thecrystal 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
Eliminationhalf-life2 hours
Identifiers
  • 6-aminohexanoic acid
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard(EPA)
ECHA InfoCard100.000.427Edit this at Wikidata
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 (also known asε-aminocaproic acid,ε-Ahx, or6-aminohexanoic acid) is a derivative and analogue of theamino acidlysine, which makes it an effectiveinhibitor forenzymes that bind that particular residue. Such enzymes includeproteolytic enzymes likeplasmin, the enzyme responsible forfibrinolysis. For this reason it is effective in treatment of certainbleeding disorders, and it is sold under the brand nameAmicar.[3] Aminocaproic acid is also an intermediate in the polymerization ofNylon-6, where it is formed by ring-opening hydrolysis ofcaprolactam. The crystal structure determination showed that the 6-aminohexanoic acid is present as a salt, at least in the solid state.[4]

Medical use

[edit]

Aminocaproic acid (Amicar) is FDA-approved for use in the treatment of acute bleeding due to elevated fibrinolytic activity.[3] It also carries anorphan drug designation from the FDA for the prevention of recurrent hemorrhage in patients with traumatichyphema.[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 acutepromyelocytic leukemia.[12]

References

[edit]
  1. ^G. J. Reiss (2010)."CSD Communication AMCAPR11: 6-Aminohexanoic acid".Cambridge Structural Database: Access Structures.Cambridge Crystallographic Data Centre.doi:10.5517/ccv38nv. Retrieved18 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. ^abc"Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet".DailyMed. 9 October 2020. Retrieved11 November 2020.
  4. ^Reiss GJ (2011),"Crystal Structure",CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre,doi:10.5517/ccv38nv, retrieved24 October 2019
  5. ^"Aminocaproic acid Orphan Drug Designations and Approvals".U.S.Food and Drug Administration (FDA). 6 January 1995. Retrieved11 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

[edit]
Antihemorrhagics
(coagulation)
Systemic
Vitamin K
Coagulation
factors
Other
systemic
Local
Antifibrinolytics
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