Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H13NO2 |
Molecular Weight | 131.1729 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCCCC(O)=O
InChI
InChIKey=SLXKOJJOQWFEFD-UHFFFAOYSA-N
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/568312
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/568312
6-Aminocaproic acid (epsilon-aminocaproic acid, marketed as Amicar) is an ant fibrinolytic agent that acts by inhibiting plasminogen activators, which have fibrinolytic properties. It is useful in enhancing hemostasis when fibrinolysis contributes to bleeding. In life threatening situations, transfusion of appropriate blood products and other emergency measures may be required. Fibrinolytic bleeding may frequently be associated with surgical complications following heart surgery (with or without cardiac bypass procedures) and portacaval shunt; hematological disorders such as a megakaryocytic thrombocytopenia (accompanying aplastic anemia); hepatic cirrhosis; and neoplastic disease such as carcinoma of the prostate, lung, stomach, and cervix. 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. The drug should NOT be administered without a definite diagnosis and/or laboratory finding indicative of hyperfibrinolysis (hyperplasminemia). Inhibition of fibrinolysis by aminocaproic acid may theoretically result in clotting or thrombosis. However, there is no definite evidence that administration of aminocaproic acid has been responsible for the few reported cases of intravascular clotting which followed this treatment. Rather, it appears that such intravascular clotting was most likely due to the patient's preexisting clinical condition, e.g., the presence of DIC. It has been postulated that extravascular clots formed in vivo may not undergo spontaneous lysis as do normal clots. Reports have appeared in the literature of an increased incidence of certain neurological deficits such as hydrocephalus, cerebral ischemia, or cerebral vasospasm associated with the use of ant fibrinolytic agents in the treatment of subarachnoid hemorrhage (SAH). All of these events have also been described as part of the natural course of SAH, or as a consequence of diagnostic procedures such as angiography. Drug relatedness remains unclear. Aminocaproic acid may change the conformation of apoliprotein, changing its binding properties and potentially preventing the formation of lipoprotein.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7301085
Curator's Comment: epsilon-Aminocaproic acid (EACA) has been used to prevent rebleeding in patients with intracranial aneurysms because it crosses the blood-brain barrier and is an inhibitor of fibrinolysis
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1801 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13896679 |
0.009 mM [Kd] | ||
Target ID: CHEMBL1873 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8073394 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | AMICAR Approved UseAMICAR is useful in enhancing hemostasis when fibrinolysis contributes to bleeding. In life threatening situations, transfusion of appropriate blood products and other emergency measures may be required. Fibrinolytic bleeding may frequently be associated with surgical complications following heart surgery (with or without cardiac bypass procedures) and portacaval shunt; hematological disorders such as amegakaryocytic thrombocytopenia (accompanying aplastic anemia); acute and life-threatening abruptio placentae; hepatic cirrhosis; and neoplastic disease such as carcinoma of the prostate, lung, stomach, and cervix. Launch Date1981 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
164 μg/mL |
5 g single, oral dose: 5 g route of administration: Oral experiment type: SINGLE co-administered: |
AMINOCAPROIC ACID plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.2 h |
5 g single, oral dose: 5 g route of administration: Oral experiment type: SINGLE co-administered: |
AMINOCAPROIC ACID plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
10 g 1 times / hour multiple, intravenous Highest studied dose Dose: 10 g, 1 times / hour Route: intravenous Route: multiple Dose: 10 g, 1 times / hour Sources: |
unhealthy, 50-74 n = 15 Health Status: unhealthy Condition: Fibrinolytic Bleeding Age Group: 50-74 Sex: M+F Population Size: 15 Sources: |
|
5 g 1 times / hour multiple, oral Recommended Dose: 5 g, 1 times / hour Route: oral Route: multiple Dose: 5 g, 1 times / hour Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Fibrinolytic Bleeding Sources: Page: p.6 |
Disc. AE: Skeletal muscle weakness... AEs leading to discontinuation/dose reduction: Skeletal muscle weakness (rare) Sources: Page: p.6 |
2 g 6 times / hour multiple, oral Studied dose Dose: 2 g, 6 times / hour Route: oral Route: multiple Dose: 2 g, 6 times / hour Sources: Page: p.6 |
unhealthy n = 1 Health Status: unhealthy Condition: Fibrinolytic Bleeding Sex: M Population Size: 1 Sources: Page: p.6 |
Disc. AE: Cerebellar hemorrhage, Cardiac disorder NOS... AEs leading to discontinuation/dose reduction: Cerebellar hemorrhage (grade 5, 1 patient) Sources: Page: p.6Cardiac disorder NOS (1 patient) Hepatic lesion (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Skeletal muscle weakness | rare Disc. AE |
5 g 1 times / hour multiple, oral Recommended Dose: 5 g, 1 times / hour Route: oral Route: multiple Dose: 5 g, 1 times / hour Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Fibrinolytic Bleeding Sources: Page: p.6 |
Cardiac disorder NOS | 1 patient Disc. AE |
2 g 6 times / hour multiple, oral Studied dose Dose: 2 g, 6 times / hour Route: oral Route: multiple Dose: 2 g, 6 times / hour Sources: Page: p.6 |
unhealthy n = 1 Health Status: unhealthy Condition: Fibrinolytic Bleeding Sex: M Population Size: 1 Sources: Page: p.6 |
Hepatic lesion | 1 patient Disc. AE |
2 g 6 times / hour multiple, oral Studied dose Dose: 2 g, 6 times / hour Route: oral Route: multiple Dose: 2 g, 6 times / hour Sources: Page: p.6 |
unhealthy n = 1 Health Status: unhealthy Condition: Fibrinolytic Bleeding Sex: M Population Size: 1 Sources: Page: p.6 |
Cerebellar hemorrhage | grade 5, 1 patient Disc. AE |
2 g 6 times / hour multiple, oral Studied dose Dose: 2 g, 6 times / hour Route: oral Route: multiple Dose: 2 g, 6 times / hour Sources: Page: p.6 |
unhealthy n = 1 Health Status: unhealthy Condition: Fibrinolytic Bleeding Sex: M Population Size: 1 Sources: Page: p.6 |
PubMed
Title | Date | PubMed |
---|---|---|
Controls exerted by the Aib residue: helix formation and helix reversal. | 2001 |
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Anti-fibrinolytic use for minimising perioperative allogeneic blood transfusion. | 2001 |
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Utilization of technologies to reduce allogeneic blood transfusion in the United States. | 2001 Apr |
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Transcriptional induction of diverse midgut trypsins in larval Agrotis ipsilon and Helicoverpa zea feeding on the soybean trypsin inhibitor. | 2001 Apr 27 |
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Identification of six chymotrypsin cDNAs from larval midguts of Helicoverpa zea and Agrotis ipsilon feeding on the soybean (Kunitz) trypsin inhibitor. | 2001 Apr 27 |
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Chronic subcutaneous octreotide decreases gastrointestinal blood loss in blue rubber-bleb nevus syndrome. | 2001 Aug |
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Pharmacokinetic mechanisms associated with synergism by DEF of cypermethrin toxicity in larval and adult Helicoverpa zea, Spodoptera frugiperda, and Agrotis ipsilon (Lepidoptera: Noctuidae). | 2001 Aug |
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Toxicity of pyrethroids and effect of synergists to larval and adult Helicoverpa zea, Spodoptera frugiperda, and Agrotis ipsilon (Lepidoptera: Noctuidae). | 2001 Aug |
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Synthesis, characterization and photodynamic activity of amino-substituted hypocrellin derivatives. | 2001 Aug |
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Postoperatively administered aprotinin or epsilon aminocaproic acid after cardiopulmonary bypass has limited benefit. | 2001 Aug |
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Design, synthesis, and biological evaluation of HIV/FIV protease inhibitors incorporating a conformationally constrained macrocycle with a small P3' residue. | 2001 Jan 22 |
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Establishment and characterization of insect cell lines from 10 lepidopteran species. | 2001 Jun |
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Comparison of epsilon aminocaproic acid and low-dose aprotinin in cardiopulmonary bypass: efficiency, safety and cost. | 2001 Mar |
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Synthesis of biotinylated bis(D-glucose) derivatives for glucose transporter photoaffinity labelling. | 2001 Mar 22 |
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Reaction of canine plasminogen with 6-aminohexanoate: a thermodynamic study combining fluorescence, circular dichroism, and isothermal titration calorimetry. | 2001 Mar 27 |
|
Interaction of amorphous calcium phosphate with fibrin in vitro causes decreased fibrinolysis and altered protease profiles: implications for atherosclerotic disease. | 2001 Oct |
|
Insertion of an N-terminal 6-aminohexanoic acid after the 7 amino acid position of glucagon-like peptide-1 produces a long-acting hypoglycemic agent. | 2001 Oct |
|
Increase in bone growth factors with healing rat fractures: the enhancing effect of zinc. | 2001 Oct |
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Antifibrinolytic agents and desmopressin as hemostatic agents in cardiac surgery. | 2001 Sep |
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Ophthalmic surgery in haemophilia. | 2001 Sep |
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Light scattering and in vitro biocompatibility studies of poly (vinyl pyrrolidone) derivatives with amino-acid-dependent groups. | 2002 |
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Renal complications of sickle cell disease: managing for optimal outcomes. | 2002 |
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Enhanced in vivo activity of peptidase-resistant analogs of the insect kinin neuropeptide family. | 2002 Apr |
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Spectrophotometric assays for L-lysine alpha-oxidase and gamma-glutamylamine cyclotransferase. | 2002 Apr 15 |
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[Macroscopic hematuria associated with sickle cell anemia trait: report of ten cases]. | 2002 Aug |
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Increasing paracellular porosity by E-cadherin peptides: discovery of bulge and groove regions in the EC1-domain of E-cadherin. | 2002 Aug |
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Effect of a synthetic carboxy-terminal peptide of alpha(2)-antiplasmin on urokinase-induced fibrinolysis. | 2002 Feb 1 |
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Enhancement of fibrinolytic activity of U937 cells by malformin A1. | 2002 Jan |
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Point-of-care testing for prothrombin time, but not activated partial thromboplastin time, correlates with laboratory methods in patients receiving aprotinin or epsilon-aminocaproic acid while undergoing cardiac surgery. | 2002 Jan |
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Clinical management of hereditary angio-oedema in children. | 2002 Jun |
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Nitric oxide: platelet protectant properties during cardiopulmonary bypass/ECMO. | 2002 Jun |
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Evidence-based EACA dosing? | 2002 Jun |
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Evaluation of progesterone-ovalbumin conjugates with different length linkers in enzyme-linked immunosorbant assay and surface plasmon resonance-based immunoassay. | 2002 Jun |
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Tissue factor is the receptor for plasminogen type 1 on 1-LN human prostate cancer cells. | 2002 Jun 15 |
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Fibrin as an alternative biopolymer to type-I collagen for the fabrication of a media equivalent. | 2002 Jun 15 |
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Enhancement effects of (R) and (S) enantiomers and the racemate of a model enhancer on permeation of theophylline through human skin. | 2002 Nov |
|
Malignant ascites fluid (MAF), including ovarian-cancer-associated MAF, contains angiostatin and other factor(s) which inhibit angiogenesis. | 2002 Sep |
|
Nerve growth cone guidance mediated by G protein-coupled receptors. | 2002 Sep |
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Fibrinolysis inhibitors adversely affect remodeling of tissues sealed with fibrin glue. | 2003 Jan |
Patents
Sample Use Guides
For the treatment of acute bleeding syndromes due to elevated fibrinolytic activity, it is suggested that 5 AMICAR (aminocaproic acid) 1000 mg Tablets or 10 AMICAR 500 mg Tablets (5 g) or 4 teaspoonfuls of AMICAR Oral Solution (5 g) be administered during the first hour of treatment, followed by a continuing rate of 1 AMICAR 1000 mg Tablet or 2 AMICAR 500 mg Tablets (1 g) or 1 teaspoonful of AMICAR Oral Solution (1.25 g) per hour. This method of treatment would ordinarily be continued for about 8 hours or until the bleeding situation has been controlled.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10838448
in vitro epsilon-aminocaproic acid (EACA) (final concentration 1.25-5 mg/ml) substantially inhibited the activity of the inhibitors, while the same concentration of EACA had no effect on other immunological reactions like red cell agglutination and immunofluorescence.
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NCI_THESAURUS |
C78311
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LIVERTOX |
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FDA ORPHAN DRUG |
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WHO-ATC |
B02AA01
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NDF-RT |
N0000175632
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N0000175632
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100000091891
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3005
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AMINOCAPROIC ACID
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C47391
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CHEMBL1046
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D015119
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DB00513
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60-32-2
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ACTIVE MOIETY