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Aminocaproic acid

April 30, 2024

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
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
  • 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 InfoCard100.000.427
Chemical and physical data
FormulaC6H13NO2
Molar mass131.175 g·mol−1
3D model (JSmol)
  • Interactive image
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) Y
  • Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N Y
  (verify)

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 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 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. 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. doi:10.1107/S0365110X67003019.
  3. ^ a b c "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 edit

  • 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.

April 30, 2024
aminocaproic, acid, this, article, needs, additional, citations, verification, please, help, improve, this, article, adding, citations, reliable, sources, unsourced, material, challenged, removed, find, sources, news, newspapers, books, scholar, jstor, june, 2. This article needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources Aminocaproic acid news newspapers books scholar JSTOR June 2016 Learn how and when to remove this message Aminocaproic acid also known as e aminocaproic acid e 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 acidSkeletal formulaBall and stick model of the zwitterionic form of the molecule found in the crystal structure 1 2 Clinical dataTrade namesAmicarAHFS Drugs comMonographMedlinePlusa608023License dataUS DailyMed Aminocaproic acidRoutes ofadministrationBy mouthATC codeB02AA01 WHO Legal statusLegal statusUS only 3 In general Prescription only Pharmacokinetic dataMetabolismKidneyElimination half life2 hoursIdentifiersIUPAC name 6 aminohexanoic acidCAS Number60 32 2 YPubChem CID564IUPHAR BPS6574DrugBankDB00513 YChemSpider548 YUNIIU6F3787206KEGGD00160 YChEBICHEBI 16586 YChEMBLChEMBL1046 YNIAID ChemDB018631CompTox Dashboard EPA DTXSID0020070ECHA InfoCard100 000 427Chemical and physical dataFormulaC 6H 13N O 2Molar mass131 175 g mol 13D model JSmol Interactive imageMelting point205 C 401 F SMILES C CCC O O CCNInChI InChI 1S C6H13NO2 c7 5 3 1 2 4 6 8 9 h1 5 7H2 H 8 9 YKey SLXKOJJOQWFEFD UHFFFAOYSA N Y verify Medical use editAminocaproic 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 edit 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 Bodor G Bednowitz AL Post B 1967 The crystal structure of e aminocaproic acid Acta Crystallographica 23 3 482 490 doi 10 1107 S0365110X67003019 a b c Amicar aminocaproic acid solution Amicar aminocaproic acid tablet DailyMed 9 October 2020 Retrieved 11 November 2020 Reiss GJ 2011 Crystal Structure CCDC 777717 Experimental Crystal Structure Determination Cambridge Crystallographic Data Centre doi 10 5517 ccv38nv retrieved 24 October 2019 Aminocaproic acid Orphan Drug Designations and Approvals U S Food and Drug Administration FDA 6 January 1995 Retrieved 11 November 2020 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 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 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 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 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 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 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 editAlkjaersig 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 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Aminocaproic acid amp oldid 1218894996, wikipedia, wiki, book, books, library,

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