Aminocaproic acid

Aminocaproic acid
	Skeletal formula
	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 ;
PubChem CID	564;
IUPHAR/BPS	6574;
DrugBank	DB00513 ;
ChemSpider	548 ;
UNII	U6F3787206;
KEGG	D00160 ;
ChEBI	CHEBI:16586 ;
ChEMBL	ChEMBL1046 ;
NIAID ChemDB	018631;
CompTox Dashboard (EPA)	DTXSID0020070 ;
ECHA InfoCard	100.000.427
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) ; Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N ;
	(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]

^ 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.
^ 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.
^ ^a ^b "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet". DailyMed. 9 October 2020. Retrieved 11 November 2020.
^ Reiss GJ (2011), "Crystal Structure", CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre, doi:10.5517/ccv38nv, retrieved 24 October 2019

[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.

[Amicar_FDA_label-3] "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

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