​Aminocaproic acid
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​Aminocaproic acid

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Aminocaproic 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.

Category
Other Unnatural Amino Acids
Catalog number
BAT-008132
CAS number
60-32-2
Molecular Formula
C6H13NO2
Molecular Weight
131.17
​Aminocaproic acid
IUPAC Name
6-aminohexanoic acid
Synonyms
Aminocaproic acid; NSC 400230; NSC-400230; NSC400230
Appearance
White crystalline powder
Purity
>98%
Density
1.0±0.1 g/cm3
Melting Point
199-205°C
Boiling Point
255.6ºC at 760 mmHg
Storage
Store at RT
Solubility
Soluble in Methanol, Water
Application
Antifibrinolytic agents
InChI
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
InChI Key
SLXKOJJOQWFEFD-UHFFFAOYSA-N
Canonical SMILES
C(CCC(=O)O)CCN
1.Study on mutual interactions and electronic structures of hyaluronan with Lysine, 6-Aminocaproic acid and Arginine.
Chytil M1, Trojan M2, Kovalenko A3. Carbohydr Polym. 2016 May 20;142:8-15. doi: 10.1016/j.carbpol.2016.01.035. Epub 2016 Jan 18.
Interactions between polyelectrolytes and oppositely charged surfactants have been in a great interest for several decades, yet the conventional surfactants may cause a problem in medical applications. Interactivity between polysaccharide hyaluronan (HA) and amino acids Lysine, 6-Aminocaproic acid (6-AcA), and Arginine as an alternative system is reported. The interactions were investigated by means of rheology and electric conductance and the electronic structures were explored by the density functional theory (DFT). Lysine exhibits the strongest interaction of all, which was manifested, e.g. by nearly 6-time drop of the initial viscosity comparing with only 1.3-time lower value in the case of 6-AcA. Arginine interaction with HA was surprisingly weaker in terms of viscosity than that of Lysine due to a lower and delocalized charge density on its guanidine group. According to the DFT calculations, the binding of Lysine to HA was found to be more flexible, while Arginine creates more rigid structure with HA.
2.Preoperative management of factor XI deficiency with therapeutic plasma exchange: A case report and literature review.
Pagano MB1, Konkle BA2, Wu Y3, Josephson N4. J Clin Apher. 2015 Dec 18. doi: 10.1002/jca.21442. [Epub ahead of print]
Patients with factor XI deficiency may have bleeding complications during surgery. Because bleeding severity and factor levels correlate poorly, factor replacement needs to be personalized based on bleeding history and type of procedure. We report a 65-year-old male with factor XI deficiency (7 IU dL-1 ) who presented before scheduled hip arthroplasty. He had a history of total hip arthroplasty complicated by bleeding, delayed healing and prosthesis removal, despite receiving prophylactic treatment with plasma infusion. For the current surgery a factor XI ≥50 IU dL-1 level was targeted. The calculated plasma infusion needed to achieve this goal was 3100 mL (14 U). Because of concerns about circulatory overload and inability to achieve target by simple infusion, prophylactic treatment with therapeutic plasma exchange (TPE) was requested. TPE was performed the morning before the surgery, using 100% plasma as replacement fluid (3912 mL of plasma), and a positive fluid balance of 631 mL.
3.Aminocaproic acid for the management of bleeding in patients on extracorporeal membrane oxygenation: Four adult case reports and a review of the literature.
Buckley LF1, Reardon DP2, Camp PC3, Weinhouse GL4, Silver DA5, Couper GS6, Connors JM7. Heart Lung. 2016 Feb 19. pii: S0147-9563(16)00012-1. doi: 10.1016/j.hrtlng.2016.01.011. [Epub ahead of print]
BACKGROUND: Extracorporeal membrane oxygenation (ECMO) is associated with a significant risk of bleeding and thrombosis. Despite high rates of bleeding and bleeding-related mortality in patients on ECMO, there is little evidence available to guide clinicians in the management of ECMO-associated bleeding.
4.Epsilon-Aminocaproic Acid Has No Association With Thromboembolic Complications, Renal Failure, or Mortality after Liver Transplantation.
Nicolau-Raducu R1, Ku TC2, Ganier DR3, Evans BM3, Koveleskie J3, Daly WJ Jr3, Fish B3, Cohen AJ4, Reichman TW4, Bohorquez HE4, Bruce DS4, Carmody IC4, Loss GE4, Gitman M5, Marshall T3, Nossaman BD3. J Cardiothorac Vasc Anesth. 2015 Dec 3. pii: S1053-0770(15)00964-7. doi: 10.1053/j.jvca.2015.12.003. [Epub ahead of print]
OBJECTIVES: To examine the role of epsilon-aminocaproic acid (EACA) administered after reperfusion of the donor liver in the incidences of thromboembolic events and acute kidney injury within 30 days after orthotopic liver transplantation. One-year survival rates between the EACA-treated and EACA-nontreated groups also were examined.
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