Aminocaproic acid

Aminocaproic acid

File:6-Aminocaproic acid.png Skeletal formula
File:Aminocaproic-acid-from-xtal-3D-bs-17.png Ball-and-stick model of the zwitterionic form of the molecule found in the crystal structure
Clinical data
Trade names	Amicar
AHFS/Drugs.com	Monograph
MedlinePlus	a608023
License data	US DailyMed: Aminocaproic_acid
Routes of administration	By mouth
ATC code	B02AA01 (WHO)
Legal status
Legal status	US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Kidney
Elimination half-life	2 hours
Identifiers
IUPAC name 6-aminohexanoic acid
CAS Number	60-32-2 checkY
PubChem CID	564
IUPHAR/BPS	6574
DrugBank	DB00513 checkY
ChemSpider	548 checkY
UNII	U6F3787206
KEGG	D00160 checkY
ChEBI	CHEBI:16586 checkY
ChEMBL	ChEMBL1046 checkY
NIAID ChemDB	018631
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C6H13NO2
Molar mass	131.175 g·mol−1
3D model (JSmol)	Interactive image
Melting point	205 °C (401 °F)
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) checkY Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N checkY
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Aminocaproic acid (also known as 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 sold under the brand name Amicar. Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam. The crystal structure determination showed that the 6-aminohexanoic acid is present as a salt, at least in the solid state.

Medical use

Aminocaproic acid (Amicar) is FDA-approved for use in the treatment of acute bleeding due to elevated fibrinolytic activity. It also carries an orphan drug designation from the FDA for the prevention of recurrent hemorrhage in patients with traumatic hyphema. In clinical practice, aminocaproic acid is frequently used off-label for control of bleeding in patients with severe thrombocytopenia, control of oral bleeding in patients with congenital and acquired coagulation disorders, control of perioperative bleeding associated with cardiac surgery, prevention of excessive bleeding in patients on anticoagulation therapy undergoing invasive dental procedures, and reduction of the risk of catastrophic hemorrhage in patients with acute promyelocytic leukemia.

Use in protein biochemistry

In biochemical analyses of membrane proteins, such as BN-PAGE, ε-aminocaproic acid is used to enhance membrane protein solubility while avoiding the addition of sodium chloride.