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Identification
NameAminocaproic Acid
Accession NumberDB00513  (APRD00791, DB04134, EXPT00408, EXPT00461)
Typesmall molecule
Groupsapproved, investigational
Description

An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
6-aminohexanoic acidNot AvailableNot Available
Acide aminocaproïqueFrenchINN
Ácido aminocapróicoSpanishINN
Acidum AminocaproicumLatinINN
AminocapronsäureGermanINN
EacaNot AvailableIS
EACANot AvailableNot Available
EpsilcapramineNot AvailableNot Available
Epsilon-Aminocaproic AcidNot AvailableJAN
SaltsNot Available
Brand names
NameCompany
AcepraminPannonpharma
AmicarClover
AmocapCelon
CaproaminRottapharm
CaprocatCatalysis
CaprolisinMenarini
E-CaproEdruc
EpsicapromNot Available
HemocidGlaxoSmithKline
InselonYing Yuan
IpronJohnson
IpsilonNikkho
Kai Nai YinWuxi
MinocapACI
PlaslloidCCPC
ResplaminShinlin Sinseng
Brand mixturesNot Available
CategoriesNot Available
CAS number60-32-2
WeightAverage: 131.1729
Monoisotopic: 131.094628665
Chemical FormulaC6H13NO2
InChI KeyInChIKey=SLXKOJJOQWFEFD-UHFFFAOYSA-N
InChI
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
IUPAC Name
6-aminohexanoic acid
SMILES
NCCCCCC(O)=O
Mass Specshow(7.2 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassFatty Acids and Conjugates
SubclassAmino Fatty Acids
Direct parentAmino Fatty Acids
Alternative parentsStraight Chain Fatty Acids; Polyamines; Enolates; Carboxylic Acids; Monoalkylamines
Substituentscarboxylic acid derivative; enolate; carboxylic acid; polyamine; primary amine; amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the amino fatty acids. These are fatty acids contaning an amine group.
Pharmacology
IndicationFor use in the treatment of excessive postoperative bleeding.
PharmacodynamicsAminocaproic 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).
AbsorptionAbsorbed 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 bindingNot 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.

SubstrateEnzymesProduct
Aminocaproic Acid
    Adipic acidDetails
    Route of eliminationRenal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.
    Half lifeThe terminal elimination half-life is approximately 2 hours.
    Clearance
    • 169 mL/min
    ToxicityA 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
    PathwaysNot Available
    SNP Mediated EffectsNot Available
    SNP Mediated Adverse Drug ReactionsNot Available
    ADMET
    Predicted ADMET features
    Property Value Probability
    Human Intestinal Absorption Not Available Not Available
    Blood Brain Barrier Not Available Not Available
    Caco-2 permeable Not Available Not Available
    P-glycoprotein substrate Not Available Not Available
    P-glycoprotein inhibitor I Not Available Not Available
    P-glycoprotein inhibitor II Not Available Not Available
    Renal organic cation transporter Not Available Not Available
    CYP450 2C9 substrate Not Available Not Available
    CYP450 2D6 substrate Not Available Not Available
    CYP450 3A4 substrate Not Available Not Available
    CYP450 1A2 substrate Not Available Not Available
    CYP450 2C9 substrate Not Available Not Available
    CYP450 2D6 substrate Not Available Not Available
    CYP450 2C19 substrate Not Available Not Available
    CYP450 3A4 substrate Not Available Not Available
    CYP450 inhibitory promiscuity Not Available Not Available
    Ames test Not Available Not Available
    Carcinogenicity Not Available Not Available
    Biodegradation Not Available Not Available
    Rat acute toxicity Not Available Not applicable
    hERG inhibition (predictor I) Not Available Not Available
    hERG inhibition (predictor II) Not Available Not Available
    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
    FormRouteStrength
    Injection, solutionIntravenous
    SyrupOral
    TabletOral
    Prices
    Unit descriptionCostUnit
    Amicar 1000 mg tablet7.17USDtablet
    Amicar 500 mg tablet3.67USDtablet
    Aminocaproic acid 500 mg tablet2.28USDtablet
    Aminocaproic acid 250 mg/ml0.06USDml
    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    PatentsNot Available
    Properties
    Statesolid
    Experimental Properties
    PropertyValueSource
    melting point205 °CPhysProp
    water solubility5.05E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
    logP-2.95HANSCH,C ET AL. (1995)
    pKa4.43 (at 25 °C)KORTUM,G ET AL (1961)
    Predicted Properties
    PropertyValueSource
    water solubility4.52e+01 g/lALOGPS
    logP-2.7ALOGPS
    logP-2ChemAxon
    logS-0.46ALOGPS
    pKa (strongest acidic)4.73ChemAxon
    pKa (strongest basic)10.21ChemAxon
    physiological charge0ChemAxon
    hydrogen acceptor count3ChemAxon
    hydrogen donor count2ChemAxon
    polar surface area63.32ChemAxon
    rotatable bond count5ChemAxon
    refractivity34.66ChemAxon
    polarizability14.71ChemAxon
    number of rings0ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterNoChemAxon
    Veber's ruleNoChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    Spectra
    References
    Synthesis Reference

    Frantisek Mares, “Process for producing caprolactam from 6-aminocaproic acid.” U.S. Patent US3988319, issued August, 1955.

    US3988319
    General ReferenceNot Available
    External Links
    ResourceLink
    KEGG DrugD00160
    KEGG CompoundC02378
    PubChem Compound564
    PubChem Substance46506934
    ChemSpider548
    ChEBI16586
    ChEMBLCHEMBL1046
    Therapeutic Targets DatabaseDAP000200
    PharmGKBPA164774947
    HETACA
    RxListhttp://www.rxlist.com/cgi/generic/amicarpre.htm
    Drugs.comhttp://www.drugs.com/cdi/aminocaproic-acid.html
    WikipediaAminocaproic_acid
    ATC CodesB02AA01
    AHFS CodesNot Available
    PDB Entries
    FDA labelshow(152 KB)
    MSDSshow(73.6 KB)
    Interactions
    Drug InteractionsNot Available
    Food InteractionsNot Available

    1. Plasminogen

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Plasminogen P00747 Details

    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

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: antagonist

    Components

    Name UniProt ID Details
    Tissue-type plasminogen activator P00750 Details

    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)

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: other

    Components

    Name UniProt ID Details
    Apolipoprotein(a) P08519 Details

    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

    1. Aldehyde oxidase

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Aldehyde oxidase Q06278 Details

    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 September 16, 2013 17:11