Aminocaproic acid

Aminocaproic acid
Skeletal formula
Ball-and-stick model of the zwitterionic form of the molecule found in the crystal structure[1][2]
Clinical data
Trade namesAmicar
AHFS/Drugs.comMonograph
MedlinePlusa608023
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismKidney
Elimination half-life2 hours
Identifiers
  • 6-aminohexanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.427 Edit this at Wikidata
Chemical and physical data
FormulaC6H13NO2
Molar mass131.175 g·mol−1
3D model (JSmol)
Melting point205 °C (401 °F)
  • C(CCC(=O)O)CCN
  • InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9) checkY
  • Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N checkY
  (verify)

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.[3] 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.[4]

  1. ^ G. J. Reiss (2010). "CSD Communication AMCAPR11: 6-Aminohexanoic acid". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/ccv38nv. Retrieved 18 August 2021.
  2. ^ Bodor G, Bednowitz AL, Post B (1967). "The crystal structure of ε-aminocaproic acid". Acta Crystallographica. 23 (3): 482–490. Bibcode:1967AcCry..23..482B. doi:10.1107/S0365110X67003019.
  3. ^ a b "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet". DailyMed. 9 October 2020. Retrieved 11 November 2020.
  4. ^ Reiss GJ (2011), "Crystal Structure", CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre, doi:10.5517/ccv38nv, retrieved 24 October 2019