Aminocaproic acid

Aminocaproic acid

Systematic (IUPAC) name
6-aminohexanoic acid
Clinical data
Trade names	Amicar
AHFS/Drugs.com	monograph
MedlinePlus	a608023
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Metabolism	Renal
Half-life	2 hours
Identifiers
CAS number	60-32-2 Y
ATC code	B02AA01
PubChem	CID 564
DrugBank	APRD00791
ChemSpider	548 Y
UNII	U6F3787206 Y
KEGG	D00160 Y
ChEBI	CHEBI:16586 Y
ChEMBL	CHEMBL1046 Y
Chemical data
Formula	C6H13NO2
Mol. mass	131.173 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9) Y Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Aminocaproic acid (also known as Amicar, 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 marketed as Amicar. Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam.

Clinical use

Aminocaproic acid is used to treat excessive postoperative bleeding, especially after procedures in which a great amount of bleeding is indicated, such as cardiac surgery. It can be given orally or intravenously. A meta-analysis found that lysine analogs like aminocaproic acid significantly reduced blood loss in patients undergoing coronary artery bypass grafting.

Aminocaproic acid can also be used to treat the overdose and/or toxic effects of the thrombolytic pharmacologic agents tissue plasminogen activator (commonly known as tPA) and streptokinase.

Side effects

Its side effects include nausea, vomiting, and chronic mild fevers (99 degrees to 100 degrees). When used long-term (for approximately 6 to 12 months), there is a risk of the inflammation of one's internal organs, especially the appendix (appendicitis) and liver, as well as failure of the liver and cyanosis. It almost always causes generalized myalgia and fibromyalgia. In some cases, successive organ failure can occur after long-term usage. However, the main risk associated with aminocaproic acid is the increased risk for thrombosis because of the inhibition of fibrinolysis.