Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H13NO2.ClH |
| Molecular Weight | 167.634 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NCCCCCC(O)=O
InChI
InChIKey=AENOKLOQCCSDAZ-UHFFFAOYSA-N
InChI=1S/C6H13NO2.ClH/c7-5-3-1-2-4-6(8)9;/h1-5,7H2,(H,8,9);1H
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1801 |
0.009 mM [Kd] | ||
Target ID: CHEMBL1873 |
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 |
|---|---|---|
| Hyperglycemic effect of amino compounds structurally related to caproate in rats. | 1975 Mar |
|
| Seizure after infusion of aminocaproic acid. | 1978 Nov 24 |
|
| Controls exerted by the Aib residue: helix formation and helix reversal. | 2001 |
|
| Development of an improved medium for germination of Cajanus cajan (L.) Millsp. pollen in vitro. | 2001 Apr |
|
| Utilization of technologies to reduce allogeneic blood transfusion in the United States. | 2001 Apr |
|
| Identification of six chymotrypsin cDNAs from larval midguts of Helicoverpa zea and Agrotis ipsilon feeding on the soybean (Kunitz) trypsin inhibitor. | 2001 Apr 27 |
|
| Chronic subcutaneous octreotide decreases gastrointestinal blood loss in blue rubber-bleb nevus syndrome. | 2001 Aug |
|
| 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 |
|
| Toxicity of pyrethroids and effect of synergists to larval and adult Helicoverpa zea, Spodoptera frugiperda, and Agrotis ipsilon (Lepidoptera: Noctuidae). | 2001 Aug |
|
| Synthesis, characterization and photodynamic activity of amino-substituted hypocrellin derivatives. | 2001 Aug |
|
| Classical and slow-binding inhibitors of human type II arginase. | 2001 Aug 7 |
|
| Effect of sepimostat mesilate on experimental venous thrombosis in rats. | 2001 Feb 1 |
|
| Regulation of urokinase plasminogen activator/plasmin-mediated invasion of melanoma cells by the integrin vitronectin receptor alphaVbeta3. | 2001 Feb 1 |
|
| Regulation of plasminogen binding to neutrophils. | 2001 Feb 15 |
|
| Prevention of the adverse effects of aprotinin in autologous fibrin glue. | 2001 Jan |
|
| Design, synthesis, and biological evaluation of HIV/FIV protease inhibitors incorporating a conformationally constrained macrocycle with a small P3' residue. | 2001 Jan 22 |
|
| Purification, cloning, and characterization of a profibrinolytic plasminogen-binding protein, TIP49a. | 2001 Jan 5 |
|
| Establishment and characterization of insect cell lines from 10 lepidopteran species. | 2001 Jun |
|
| Plasminogen binding is increased with adipocyte differentiation. | 2001 Jun 8 |
|
| Comparison of epsilon aminocaproic acid and low-dose aprotinin in cardiopulmonary bypass: efficiency, safety and cost. | 2001 Mar |
|
| Heart transplant in a factor VIII-deficient patient with a high-titre inhibitor: perioperative management using high-dose continuous infusion factor VIII and recombinant factor VIIa. | 2001 Mar |
|
| Influence of sugar chain on fibrin affinity of recombinant t-PA. | 2001 Mar |
|
| Reaction of canine plasminogen with 6-aminohexanoate: a thermodynamic study combining fluorescence, circular dichroism, and isothermal titration calorimetry. | 2001 Mar 27 |
|
| The Effect of epsilon-aminocaproic acid on perioperative blood loss in patients with idiopathic scoliosis undergoing posterior spinal fusion: a preliminary prospective study. | 2001 May 15 |
|
| Interaction of amorphous calcium phosphate with fibrin in vitro causes decreased fibrinolysis and altered protease profiles: implications for atherosclerotic disease. | 2001 Oct |
|
| Black cutworm (Lepidoptera: Noctuidae) larval emigration and biomass in mixtures of endophytic perennial ryegrass and Kentucky bluegrass. | 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 |
|
| Ophthalmic surgery in haemophilia. | 2001 Sep |
|
| Intraoperative plateletpheresis and autologous platelet gel do not reduce chest tube drainage or allogeneic blood transfusion after reoperative coronary artery bypass graft. | 2001 Sep |
|
| Aprotinin but not epsilon-aminocaproic acid decreases interleukin-10 after cardiac surgery with extracorporeal circulation: randomized, double-blind, placebo-controlled study in patients receiving aprotinin and epsilon-aminocaproic acid. | 2001 Sep 18 |
|
| The structure of lipoprotein(a) and ligand-induced conformational changes. | 2001 Sep 4 |
|
| Renal complications of sickle cell disease: managing for optimal outcomes. | 2002 |
|
| Enhanced in vivo activity of peptidase-resistant analogs of the insect kinin neuropeptide family. | 2002 Apr |
|
| Antiapoptotic and proapoptotic action of various amino acids and analogs in starving MOLT-4 cells. | 2002 Feb 1 |
|
| Comparative analyses of the lysine binding site properties of apolipoprotein(a) kringle IV types 7 and 10. | 2002 Jan 29 |
|
| [Suppression of cytomegalovirus infection in cell system by fullerene amino acid derivates]. | 2002 Jan-Feb |
|
| Furosemide: progress in understanding its diuretic, anti-inflammatory, and bronchodilating mechanism of action, and use in the treatment of respiratory tract diseases. | 2002 Jul-Aug |
|
| Nitric oxide: platelet protectant properties during cardiopulmonary bypass/ECMO. | 2002 Jun |
|
| The effect of epsilon aminocaproic acid on blood loss in patients who undergo primary total hip replacement: a pilot study. | 2002 Jun |
|
| Evaluation of progesterone-ovalbumin conjugates with different length linkers in enzyme-linked immunosorbant assay and surface plasmon resonance-based immunoassay. | 2002 Jun |
|
| Tissue factor is the receptor for plasminogen type 1 on 1-LN human prostate cancer cells. | 2002 Jun 15 |
|
| Predictors of pericardial effusion after orthotopic heart transplantation. | 2002 Nov |
|
| Malignant ascites fluid (MAF), including ovarian-cancer-associated MAF, contains angiostatin and other factor(s) which inhibit angiogenesis. | 2002 Sep |
|
| Safety and efficacy of methods for reducing perioperative allogeneic transfusion: a critical review of the literature. | 2002 Sep-Oct |
|
| Acridine conjugates of 3-clip-phen: influence of the linker on the synthesis and the DNA cleavage activity of their copper complexes. | 2002 Sep-Oct |
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
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m1697
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SUBSTANCE RECORD
