Aminocaproic acid

Systematic (IUPAC) name
6-aminohexanoic acid
Identifiers
CAS number	60-32-2
ATC code	B02AA01
PubChem	564
DrugBank	APRD00791
ChemSpider	9103
Chemical data
Formula	C6H13NO2
Mol. mass	131.173 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	Renal
Half life	2 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?
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Aminocaproic acid (also known as Amicar, ε-amino caproic acid, 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 some bleeding disorders and is marketed as Amicar.

Contents 1 Mechanism of action 2 Clinical use 2.1 Side effects 3 Other uses 4 References

[edit] Mechanism of action

Aminocaproic acid works as an anti-fibrinolytic or anti-proteolytic. As a lysine analogue, it binds reversibly to the kringle domain of the enzymogen plasminogen. Thus plasminogen cannot be activated (by its activators) to plasmin, which then cannot split fibrin (anti-fibrinolytic effect).

[edit] Clinical use

Aminocaproic acid is used to treat excessive postoperative bleeding. It can be given orally or intravenously. One scenario wherein it may be useful is to treat bleeding after dental extractions in patients with hemophilia, because the oral mucosa is rich in plasminogen activators. A meta-analysis found that lysine analogs like aminocaproic acid significantly reduced blood loss in patients undergoing coronary artery bypass grafting.^{[citation needed]}

[edit] Side effects

Its side effects are mainly related to the gastrointestinal tract and include nausea, vomiting, abdominal pain, and diarrhea. It may cause generalised myalgia. The main risk associated with aminocaproic acid is the increased risk for thrombosis because of the inhibition of fibrinolysis.

[edit] Other uses

Aminocaproic acid is occasionally used in BN-PAGE buffers, not for its effects as a proteolysis inhibitor, but to solubilize membrane proteins in place of sodium chloride (which is incompatible with PAGE in the necessary concentration). Percent recovery of protein complexes increases linearly with the concentration of inhibitor (between 125 mM and 750 mM)^[1].

[edit] References

This article does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (November 2007)

1. ^ Schägger, H and Von Jagow, G (1991). Blue Native Electrophoresis for Isolation of Membrane Protein Complexes in Enzymatically Active Form. Analytical Biochemistry 199 (2): 223-231.

v • d • e Antihemorrhagics (B02) Hemostatics (coagulation) Systemic Vitamin K Phytomenadione/K1 · Menadione/K3 Coagulation factors intrinsic: IX/Nonacog alfa · VIII extrinsic: VII/Eptacog alfa common: X · II/Thrombin · I/Fibrinogen Other systemic Etamsylate · Carbazochrome · Batroxobin · thrombopoietin receptor agonist (Romiplostim, Eltrombopag) Local Absorbable gelatin sponge · Oxidized cellulose · Tetragalacturonic acid hydroxymethylester · Thrombin · Collagen · Calcium alginate · Epinephrine/Adrenalone Antifibrinolytics amino acids (Aminocaproic acid, Tranexamic acid, Aminomethylbenzoic acid) serpins (Aprotinin, Alfa1 antitrypsin, C1-inhibitor, Camostat)