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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-Aminocaproic acidNot AvailableNot Available
6-aminohexanoic acidNot AvailableNot Available
Acide aminocaproïqueFrenchINN
Acide aminocaproqueNot AvailableNot Available
Ácido aminocapróicoSpanishINN
Acidum AminocaproicumLatinINN
AhxNot AvailableNot Available
AMICARNot AvailableNot Available
AMINOCAPROICNot AvailableNot Available
Aminocaproic acidNot AvailableNot Available
AminocapronsäureGermanINN
Aminohexanoic acidNot AvailableNot Available
CaproaminNot AvailableNot Available
EacaNot AvailableIS
EACANot AvailableNot Available
EpsicapromNot AvailableNot Available
EpsilcapramineNot AvailableNot Available
epsilon-AhxNot AvailableNot Available
Epsilon-Aminocaproic AcidNot AvailableJAN
epsilon-Aminohexanoic acidNot AvailableNot Available
ZNot AvailableNot Available
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 KeySLXKOJJOQWFEFD-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
Not Available
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 Solubility45.2ALOGPS
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 Area63.32 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.66 m3·mol-1ChemAxon
Polarizability14.71 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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

Targets

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

Enzymes

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11