ACA

6-AMINOHEXANOIC ACID

ACA in polymers: 22 entries. Examples include: 1ILQ 3DRQ 6AU5

ACA as a free ligand exists in 30 entries. Examples include: 3A66 3KIV 1KQS

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View summary at Ligand Expo



Chemical Component Summary

Name6-AMINOHEXANOIC ACID
Identifiers6-aminohexanoic acid
FormulaC6 H13 N O2
Molecular Weight131.17
TypePEPTIDE LINKING
Isomeric SMILESNCCCCCC(O)=O
InChIInChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
InChIKeySLXKOJJOQWFEFD-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count22
Chiral Atom Count0
Chiral Atomsn/a
Bond Count21
Aromatic Bond Count0
Leaving AtomsO2, HO2, HN62

Drug Info: DrugBank

DrugBank IDDB00513 Different stereochemistry
NameAminocaproic Acid
Groups
  • approved
  • investigational
DescriptionAn antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]
Synonyms
  • 6-Aminocaproic acid
  • 6-aminohexanoic acid
  • Acide aminocaproïque
  • Acide aminocaproque
  • Ácido aminocapróico
Brand Names
  • Amicar
  • Aminocaproic Acid
  • Exoden White Tooth
  • Acepramin
  • Amocap
Affected OrganismHumans and other mammals
IndicationFor use in the treatment of excessive postoperative bleeding.
PharmacologyAminocaproic acid works as an antifibrinolytic. It is a derivative of the amino acid lysine. The fibrinolysis-inhibitory effects of aminocaproic acid appear to be exerted principally via inhibition of plasminogen activators and to a lesser degree through antiplasmin activity. Aminocaproic acid may be a possible prophylactic for vascular disease, as it may prevent formation of lipoprotein (a), a risk factor for vascular disease.
Mechanism of actionAminocaproic acid binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin. With NO activation of plasmin, there is a reduction in fibrinolysis. This consequently will reduce the amount of bleeding post surgery. Elevated plasma levels of lipoprotein(a) have been shown to increase the risk of vascular disease. Lipoprotein 9a)a has two components, apolipoprotein B-100, linked to apolipoprotein (a). Aminocaproic acid may change the conformation of apoliprotein (a), changing its binding properties and potentially preventing the formation of lipoprotein (a).
Route of administration
  • Intravenous
  • Oral
  • Topical
Categories
  • Acids, Acyclic
  • Amino Acids
  • Amino Acids, Peptides, and Proteins
  • Aminocaproates
  • Antifibrinolytic Agents
ATC-CodeB02AA01
CAS number60-32-2
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682