Aminocaproic acid

Aminocaproic acid

Systematic (IUPAC) name
6-aminohexanoic acid
Clinical data
Trade names	Amicar
AHFS/Drugs.com	monograph
MedlinePlus	a608023
Legal status	℞ (Prescription only)
Pharmacokinetic data
Metabolism	Renal
Biological half-life	2 hours
Identifiers
CAS Number	60-32-2 Y
ATC code	B02AA01 (WHO)
PubChem	CID: 564
IUPHAR/BPS	6574
DrugBank	DB00513 Y
ChemSpider	548 Y
UNII	U6F3787206 Y
KEGG	D00160 Y
ChEBI	CHEBI:16586 Y
ChEMBL	CHEMBL1046 Y
NIAID ChemDB	018631
Chemical data
Formula	C6H13NO2
Molecular mass	131.173 g/mol
SMILES C(CCC(=O)O)CCN
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
Physical data
Melting point	205 °C (401 °F)
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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 expected, 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.

Bleeding due to elevated fibrinolytic activity

Aminocaproic acid is used for the treatment of excessive bleeding resulting from systemic hyperfibrinolysis and urinary fibrinolysis. In life-threatening situations, fresh whole blood, fibrinogen infusions, and other emergency measures also may be required.

Aminocaproic acid is used in systemic hyperfibrinolysis associated with surgical complications following heart surgery (with or without cardiac bypass procedures) and portacaval shunt; in carcinoma of the lung, prostate, cervix, or stomach; in abruptio placentae; and in hematologic disorders such as amegakaryocytic thrombocytopenia accompanying aplastic anemia (reduces the need for platelet transfusions).

Aminocaproic acid is used in urinary fibrinolysis associated with complications of severe trauma, anoxia, and shock, and as manifested by surgical hematuria especially following prostatectomy and nephrectomy, or in nonsurgical hematuria accompanying polycystic or neoplastic disease of the GU tract.

Aminocaproic acid is used in conjunction with heparin therapy in patients with acute promyelocytic leukemia. Use is not currently included in the labeling approved by the US Food and Drug Administration. It is used as initiate therapy when plasma α2-antiplasmin (α2-plasmin inhibitor) levels have decreased to <40% of normal levels.

Ocular hemorrhage

Aminocaproic acid has been used effectively for the prevention of secondary ocular hemorrhage in patients with nonperforating traumatic hyphema (Use is not currently included in the labeling approved by the US Food and Drug Administration.). Designated an orphan drug by FDA for topical treatment of traumatic hyphema.

Hereditary hemorrhagic telangiectasia

Aminocaproic acid has been used orally for the management of hereditary hemorrhagic telangiectasia. This use is not currently included in the labeling approved by the US Food and Drug Administration.

Side effects include Confusion, Vision decrease, Vomiting, Headache, Convulsions, Malaise, Muscle weakness, Dizziness, Tinnitus, Nausea, Bradycardia, Thrombosis, Edema, Hypotension, Stroke, Syncope, Intracranial hypertension, Peripheral ischemia, Pulmonary embolism, Dyspnea, Congestion, Diarrhea, Abdominal pain, Leukopenia, Agranulocytosis, Coagulation disorder, Dry ejaculation, Injection site reactions (pain/necrosis), Pruritus, Rash, Renal failure, Anaphylaxis, and risk for myalgia.