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Identification
Name Aminocaproic Acid
Accession Number DB00513 (APRD00791, EXPT00408)
Type small molecule
Groups approved
Description

An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
6-aminohexanoic acid
ACS
Aminocaproate
Aminocaproic
E-aminocaproic acid
ε-Ahx
ε-amino caproic acid
Salts Not Available
Brand names
Name Company
Acepramin
Acepramine
Afibrin
Amicar
Amikar
Aminokapron
Atsemin
Caplamin
Capracid
Capramol
Capranol
Caprocid
Caprolisin
EACA
EACS
Epsamon
Epsicapron
Epsikapron
Epsilcapramin
Epsilcapramine
Hemocaprol
Hemopar
Hepin
Ipsilon
Respramin
First Prev Next Last
Brand mixtures Not Available
Categories
  • Antifibrinolytic Agents
CAS number 60-32-2
Weight Average: 131.1729
Monoisotopic: 131.094628665
Chemical Formula C6H13NO2
InChI Key InChIKey=SLXKOJJOQWFEFD-UHFFFAOYSA-N
InChI
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
Plain Text
IUPAC Name
6-aminohexanoic acid
SMILES
NCCCCCC(O)=O
Plain Text
Mass Spec show (7.2 KB)
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
  • Carboxylic Acids and Derivatives
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
Pharmacology
Indication For use in the treatment of excessive postoperative bleeding.
Pharmacodynamics Aminocaproic 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 action Aminocaproic 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).
Absorption Absorbed rapidly following oral administration. In adults, oral absorption appears to be a zero-order process with an absorption rate of 5.2 g/hr. The mean lag time in absorption is 10 minutes. After a single oral dose of 5 g, absorption was complete (F=1).
Volume of distribution
  • 23.1 ± 6.6 L
Protein binding Not Available
Metabolism Sixty-five percent of the dose is recovered in the urine as unchanged drug and 11% of the dose appears as the metabolite adipic acid.
Route of elimination Renal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.
Half life The terminal elimination half-life is approximately 2 hours.
Clearance
  • 169 mL/min
Toxicity A few cases of acute overdosage with intravenous administration have been reported. The effects have ranged from no reaction to transient hypotension to severe acute renal failure leading to death. The intravenous and oral LD50 were 3.0 and 12.0 g/kg respectively in the mouse and 3.2 and 16.4 g/kg respectively in the rat. An intravenous infusion dose of 2.3 g/kg was lethal in the dog.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00286 Aminocaproic Acid Pathway SMP00286
Pharmacoeconomics
Manufacturers
  • Xanodyne pharmaceutics inc
  • Abraxis pharmaceutical products
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Mikart inc
Packagers
Dosage forms
Form Route Strength
Injection, solution Intravenous
Syrup Oral
Tablet Oral
Prices
Unit description Cost Unit
Amicar 1000 mg tablet 7.17 USD tablet
Amicar 500 mg tablet 3.67 USD tablet
Aminocaproic acid 500 mg tablet 2.28 USD tablet
Aminocaproic acid 250 mg/ml 0.06 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 205 °C PhysProp
water solubility 5.05E+005 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -2.95 HANSCH,C ET AL. (1995)
pKa 4.43 (at 25 °C) KORTUM,G ET AL (1961)
Predicted Properties
Property Value Source
water solubility 4.52e+01 g/l ALOGPS
logP -2.7 ALOGPS
logP -2 ChemAxon
logS -0.46 ALOGPS
pKa (strongest acidic) 4.73 ChemAxon
pKa (strongest basic) 10.21 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 63.32 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 34.66 ChemAxon
polarizability 14.71 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00160 Link_out
KEGG Compound C02378 Link_out
PubChem Compound 564 Link_out
PubChem Substance 46506934 Link_out
ChemSpider 548 Link_out
ChEBI 16586 Link_out
ChEMBL 16586 Link_out
Therapeutic Targets Database DAP000200 Link_out
PharmGKB PA164774947 Link_out
HET ACA Link_out
RxList http://www.rxlist.com/cgi/generic/amicarpre.htm Link_out
Drugs.com http://www.drugs.com/cdi/aminocaproic-acid.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Aminocaproic_acid Link_out
ATC Codes
  • B02AA01
AHFS Codes Not Available
PDB Entries
FDA label show (152 KB)
MSDS show (73.6 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Plasminogen

Pharmacological action: yes
Actions: inhibitor

Angiostatin is an angiogenesis inhibitor that blocks neovascularization and growth of experimental primary and metastatic tumors in vivo

Organism class: human
UniProt ID: P00747 Link_out
Gene: PLG Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mochalkin I, Cheng B, Klezovitch O, Scanu AM, Tulinsky A: Recombinant kringle IV-10 modules of human apolipoprotein(a): structure, ligand binding modes, and biological relevance. Biochemistry. 1999 Feb 16;38(7):1990-8. Pubmed
  2. Prandota J, Pankow-Prandota L, Kotecki L: Impaired activation of the fibrinolytic system in children with Henoch-Schonlein purpura: beneficial effect of hydrocortisone plus Sigma-aminocaproic acid therapy on disappearance rate of cutaneous vasculitis and fibrinolysis. Am J Ther. 2001 Jan-Feb;8(1):11-9. Pubmed
  3. Lee KN, Jackson KW, McKee PA: Effect of a synthetic carboxy-terminal peptide of alpha(2)-antiplasmin on urokinase-induced fibrinolysis. Thromb Res. 2002 Feb 1;105(3):263-70. Pubmed
  4. Sun Z, Chen YH, Wang P, Zhang J, Gurewich V, Zhang P, Liu JN: The blockage of the high-affinity lysine binding sites of plasminogen by EACA significantly inhibits prourokinase-induced plasminogen activation. Biochim Biophys Acta. 2002 Apr 29;1596(2):182-92. Pubmed
  5. Kanalas JJ: Analysis of plasmin binding and urokinase activation of plasminogen bound to the Heymann nephritis autoantigen, gp330. Arch Biochem Biophys. 1992 Dec;299(2):255-60. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Tissue-type plasminogen activator

Pharmacological action: yes
Actions: antagonist

Converts the abundant, but inactive, zymogen plasminogen to plasmin by hydrolyzing a single Arg-Val bond in plasminogen. By controlling plasmin-mediated proteolysis, it plays an important role in tissue remodeling and degradation, in cell migration and many other physiopathological events. Play a direct role in facilitating neuronal migration

Organism class: human
UniProt ID: P00750 Link_out
Gene: PLAT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Husain SS, Hasan AA, Budzynski AZ: Differences between binding of one-chain and two-chain tissue plasminogen activators to non-cross-linked and cross-linked fibrin clots. Blood. 1989 Aug 15;74(3):999-1006. Pubmed
  2. Urano T, Sator de Serrano V, Gaffney PJ, Castellino FJ: Effectors of the activation of human [Glu1]plasminogen by human tissue plasminogen activator. Biochemistry. 1988 Aug 23;27(17):6522-8. Pubmed
  3. Tran-Thang C, Vouillamoz D, Kruithof EK, Sordat B: Human Co115 colon carcinoma cells potentiate the degradation of laminin mediated by tissue-type plasminogen activator. J Cell Physiol. 1994 Nov;161(2):285-92. Pubmed
  4. Krishnamurti C, Vukelja SJ, Alving BM: Inhibitory effects of lysine analogues on t-PA induced whole blood clot lysis. Thromb Res. 1994 Mar 15;73(6):419-30. Pubmed

3. Apolipoprotein(a)

Pharmacological action: unknown
Actions: other

Apo(a) is the main constituent of lipoprotein(a) (Lp(a)). It has serine proteinase activity and is able of autoproteolysis. Inhibits tissue-type plasminogen activator 1. Lp(a) may be a ligand for megalin/Gp 330

Organism class: human
UniProt ID: P08519 Link_out
Gene: LPA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Becker L, Cook PM, Koschinsky ML: Identification of sequences in apolipoprotein(a) that maintain its closed conformation: a novel role for apo(a) isoform size in determining the efficiency of covalent Lp(a) formation. Biochemistry. 2004 Aug 10;43(31):9978-88. Pubmed
Enzymes

1. Aldehyde oxidase

Actions: substrate

An aldehyde + H(2)O + O(2) = a carboxylic acid + H(2)O(2)

UniProt ID: Q06278 Link_out
Gene: AOX1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Subramanyam B, Callery PS, Geelhaar LA, Egorin MJ: A cyclic imine intermediate in the in vitro metabolic conversion of 1,6-diaminohexane to 6-aminohexanoic acid and caprolactam. Xenobiotica. 1989 Jan;19(1):33-42. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19