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Identification
NameAminocaproic Acid
Accession NumberDB00513  (APRD00791, EXPT00408, EXPT00461, DB04134)
TypeSmall Molecule
GroupsApproved, Investigational
Description

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

Structure
Thumb
Synonyms
6-Aminocaproic acid
6-aminohexanoic acid
Acide aminocaproïque
Acide aminocaproque
Ácido aminocapróico
Acidum Aminocaproicum
Ahx
AMICAR
AMINOCAPROIC
Aminocaproic acid
Aminocapronsäure
Aminohexanoic acid
Caproamin
Eaca
EACA
Epsicaprom
Epsilcapramine
epsilon-Ahx
Epsilon-Aminocaproic Acid
epsilon-Aminohexanoic acid
Z
External Identifiers
  • CL 10304
  • CY 116
  • JD 177
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amicartablet500 mg/1oralClover Pharmaceuticals Corp.2015-06-01Not applicableUs
Amicarsolution.25 g/mLoralClover Pharmaceuticals Corp.2015-06-01Not applicableUs
Amicartablet1000 mg/1oralClover Pharmaceuticals Corp.2015-06-01Not applicableUs
Aminocaproic Acidtablet1000 mg/1oralVersa Pharm Incorporated2012-06-01Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aminocaproic Acidinjection, solution250 mg/mLintravenousHospira, Inc.1987-03-09Not applicableUs
Aminocaproic Acidtablet500 mg/1oralVersa Pharm Incorporated2001-08-01Not applicableUs
Aminocaproic Acidsyrup.25 g/mLoralVersa Pharm Incorporated2000-03-01Not applicableUs
Aminocaproic Acidinjection, solution250 mg/mLintravenousAmerican Regent, Inc.1990-09-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcepraminPannonpharma
AmocapCelon
CaproaminRottapharm
CaprocatCatalysis
CaprolisinMenarini
E-CaproEdruc
EpsicapromNot Available
HemocidGlaxoSmithKline
InselonYing Yuan
IpronJohnson
IpsilonNikkho
Kai Nai YinWuxi
MinocapACI
PlaslloidCCPC
ResplaminShinlin Sinseng
Brand mixtures
NameLabellerIngredients
Exoden White ToothLifeon Corp.
SaltsNot Available
Categories
UNIIU6F3787206
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Amino fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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).
Related Articles
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
Pathways
PathwayCategorySMPDB ID
Aminocaproic Acid Action PathwayDrug actionSMP00286
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Solutionoral.25 g/mL
Tabletoral1000 mg/1
Tabletoral500 mg/1
Injection, solutionintravenous250 mg/mL
Syruporal.25 g/mL
Pastetopical
Prices
Unit descriptionCostUnit
Amicar 1000 mg tablet7.17USD tablet
Amicar 500 mg tablet3.67USD tablet
Aminocaproic acid 500 mg tablet2.28USD tablet
Aminocaproic acid 250 mg/ml0.06USD ml
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 Solubility45.2 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.2 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00ds-3900000000-d2bae6c296c96fbad8d6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9700000000-96516a7056d0134fe91fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-3900000000-b1e222c28c8ee5ee7e39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-01p9-7900000000-7b0c4a3576914da3beb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014i-9100000000-6d1cca409e0604efbe03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pdi-9000000000-a55855076c25405ac1e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-a47431cd716ecb19b9e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-a5934cb182440e097505View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9100000000-fe8764f31273202c4192View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-d811796a47319a78c0acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-85516d2ef8e256aa32c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-b263ad88d0bb4ca9e2a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-02ta-9400000000-6fd9244fa9d4129efb9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-e57b77ac2660e8633c45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05ox-9000000000-ac37660729ea0447a3b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-052f-9000000000-dd2777a39a8decd7066dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-02t9-8900000000-024692ea60c820275defView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

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

US3988319
General ReferencesNot Available
External Links
ATC CodesB02AA01
AHFS CodesNot Available
PDB Entries
FDA labelDownload (152 KB)
MSDSDownload (73.6 KB)
Interactions
Drug Interactions
Drug
Coagulation Factor IXThe risk or severity of adverse effects can be increased when Aminocaproic Acid is combined with Coagulation Factor IX.
Fibrinogen Concentrate (Human)The risk or severity of adverse effects can be increased when Aminocaproic Acid is combined with Fibrinogen Concentrate (Human).
Prothrombin complex concentrateAminocaproic Acid may increase the thrombogenic activities of Prothrombin complex concentrate.
TretinoinTretinoin may increase the thrombogenic activities of Aminocaproic Acid.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type peptidase activity
Specific Function:
Plasmin dissolves the fibrin of blood clots and acts as a proteolytic factor in a variety of other processes including embryonic development, tissue remodeling, tumor invasion, and inflammation. In ovulation, weakens the walls of the Graafian follicle. It activates the urokinase-type plasminogen activator, collagenases and several complement zymogens, such as C1 and C5. Cleavage of fibronectin ...
Gene Name:
PLG
Uniprot ID:
P00747
Molecular Weight:
90568.415 Da
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:10026282 ]
  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:11304653 ]
  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:11927133 ]
  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:12007600 ]
  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:1280065 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Serine-type endopeptidase activity
Specific Function:
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. Plays a direct role in facilitating neuronal migration.
Gene Name:
PLAT
Uniprot ID:
P00750
Molecular Weight:
62916.495 Da
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:2502209 ]
  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:3146348 ]
  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:7962113 ]
  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:8073394 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other
General Function:
Serine-type endopeptidase activity
Specific Function:
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.
Gene Name:
LPA
Uniprot ID:
P08519
Molecular Weight:
501316.005 Da
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:17139284 ]
  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:17016423 ]
  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:15287725 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xanthine dehydrogenase activity
Specific Function:
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Participates in the bioactivation of prodrugs such as famciclovir, catalyz...
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular Weight:
147916.735 Da
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:2502880 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23