Aminocaproic Acid

Aminocaproic Acid

Cat Number
PIPB-0094
CAS Number
60-32-2

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CAS Number
60-32-2
EINECS
200-469-3
Storage
Store at room temperature
Synonyms
6-Aminocaproic acid; Hexanoic acid, 6-amino-; Epsilcapramin; Capramol; Acepramine; Caprolisin
Molecular Formula
C6H13NO2
Molecular Weight
131.17
Smiles
C(CCC(=O)O)CCN
Appearance
White to off-white powder
Melting Point
207-209℃
Boiling Point
242.49℃
General Description
Aminocaproic acid is a synthetic lysine analogue that functions as an antifibrinolytic agent, available in oral and intravenous formulations. It is a specific inhibitor of plasminogen activation designed to stabilize clot formation in settings of excessive fibrinolysis. This compound is structurally related to the amino acid lysine and acts by competing for binding sites on plasminogen.
Mechanism of Action
Aminocaproic acid reversibly binds to the lysine-binding sites on plasminogen and plasmin, preventing their interaction with fibrin. This competitive inhibition blocks the conversion of plasminogen to plasmin and inhibits the proteolytic activity of plasmin once formed. By preserving the fibrin meshwork of formed clots, it effectively arrests bleeding caused by hyperfibrinolysis without directly affecting coagulation factor synthesis.
Application
It is indicated for the treatment of acute bleeding episodes resulting from elevated fibrinolytic activity, particularly in the setting of cardiac surgery with cardiopulmonary bypass and in patients with hematologic disorders such as acute promyelocytic leukemia. It is also utilized for the management of traumatic hyphema to prevent rebleeding and for the control of excessive postoperative bleeding. Off-label uses include reducing menstrual blood loss in women with menorrhagia.

A meta‑analysis of 3 randomized controlled trials and 4 non‑randomized studies assessed intravenous aminocaproic acid in primary total hip or knee arthroplasty. Pooled analysis showed significant reductions in total blood loss (MD ‑495.80 mL), drainage volume (MD ‑249.43 mL), transfusion rates (RD ‑0.17), transfusion units per patient (MD ‑0.28), and length of hospital stay (MD ‑0.33 days) with aminocaproic acid versus control. Postoperative hemoglobin was significantly higher, while deep vein thrombosis risk did not differ. The authors conclude that aminocaproic acid effectively reduces blood loss and transfusion requirements without increasing thromboembolic risk.

Fig. 1 Flow chart of the study selection and inclusion process. (Li YJ, <i>et al</i>., 2018) Fig. 1 Flow chart of the study selection and inclusion process. (Li YJ, et al., 2018)

References

  1. Li YJ, et al. The efficacy of intravenous aminocaproic acid in primary total hip and knee arthroplasty: a meta-analysis. J Orthop Surg Res. 2018; 13(1):89.

Does Aminocaproic Acid require protection from moisture during storage?

It is slightly hygroscopic. While not highly moisture-sensitive, storage in tightly sealed containers in a dry environment is recommended to prevent caking.

What is the recommended storage temperature for Aminocaproic Acid?

Store at controlled room temperature, between 15°C and 30°C. It is thermally stable under normal conditions but should be protected from excessive heat.

Is Aminocaproic Acid stable in aqueous solutions for intravenous administration?

Yes, it has good stability in aqueous solutions. We provide detailed stability data for various concentrations and recommend neutral pH for optimal long-term stability.

How is the purity of Aminocaproic Acid verified for injectable formulations?

We use a validated HPLC method to monitor related amino acid impurities and degradation products, ensuring they meet strict limits for parenteral use.
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