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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39000 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11375809/ |
150 mg/kg single, intravenous dose: 150 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMINOCAPROIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25723765/ |
30 mg/kg/h single, intravenous dose: 30 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
AMINOCAPROIC ACID plasma | Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE 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 |
|
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Skeletal muscle weakness... AEs leading to discontinuation/dose reduction: Skeletal muscle weakness (rare) Sources: |
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: |
unhealthy Health Status: unhealthy Sex: M Sources: |
Disc. AE: Cerebellar hemorrhage, Cardiac disorder NOS... AEs leading to discontinuation/dose reduction: Cerebellar hemorrhage (grade 5, 1 patient) Sources: Cardiac 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sex: M Sources: |
| 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: |
unhealthy Health Status: unhealthy Sex: M Sources: |
| 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: |
unhealthy Health Status: unhealthy Sex: M Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fibrinolysis inhibitors adversely affect remodeling of tissues sealed with fibrin glue. | 2003-01 |
|
| Enhancement effects of (R) and (S) enantiomers and the racemate of a model enhancer on permeation of theophylline through human skin. | 2002-11 |
|
| Predictors of pericardial effusion after orthotopic heart transplantation. | 2002-11 |
|
| Safety and efficacy of methods for reducing perioperative allogeneic transfusion: a critical review of the literature. | 2002-09-19 |
|
| Acridine conjugates of 3-clip-phen: influence of the linker on the synthesis and the DNA cleavage activity of their copper complexes. | 2002-09-19 |
|
| The effects of ultrafiltration on e-aminocaproic acid: an in vitro analysis. | 2002-09 |
|
| Malignant ascites fluid (MAF), including ovarian-cancer-associated MAF, contains angiostatin and other factor(s) which inhibit angiogenesis. | 2002-09 |
|
| Nerve growth cone guidance mediated by G protein-coupled receptors. | 2002-09 |
|
| [Macroscopic hematuria associated with sickle cell anemia trait: report of ten cases]. | 2002-08 |
|
| Increasing paracellular porosity by E-cadherin peptides: discovery of bulge and groove regions in the EC1-domain of E-cadherin. | 2002-08 |
|
| Evolution of noctuid pheromone binding proteins: identification of PBP in the black cutworm moth, Agrotis ipsilon. | 2002-08 |
|
| Furosemide: progress in understanding its diuretic, anti-inflammatory, and bronchodilating mechanism of action, and use in the treatment of respiratory tract diseases. | 2002-07-13 |
|
| Epsilon-aminocaproic acid and renal complications: case report and review of the literature. | 2002-07 |
|
| Tissue factor is the receptor for plasminogen type 1 on 1-LN human prostate cancer cells. | 2002-06-15 |
|
| Fibrin as an alternative biopolymer to type-I collagen for the fabrication of a media equivalent. | 2002-06-15 |
|
| Clinical management of hereditary angio-oedema in children. | 2002-06 |
|
| Nitric oxide: platelet protectant properties during cardiopulmonary bypass/ECMO. | 2002-06 |
|
| The effect of epsilon aminocaproic acid on blood loss in patients who undergo primary total hip replacement: a pilot study. | 2002-06 |
|
| The effect of 6-aminohexanoic acid and fucoidan on the activation of glutamic plasminogen by streptokinase. | 2002-06 |
|
| Refractory hyperkalaemia associated with use of epsilon-aminocaproic acid during coronary bypass in a dialysis patient. | 2002-06 |
|
| Evidence-based EACA dosing? | 2002-06 |
|
| Evaluation of progesterone-ovalbumin conjugates with different length linkers in enzyme-linked immunosorbant assay and surface plasmon resonance-based immunoassay. | 2002-06 |
|
| Synthesis and biodistribution of 211At-labeled, biotinylated, and charge-modified poly-L-lysine: evaluation for use as an effector molecule in pretargeted intraperitoneal tumor therapy. | 2002-05-16 |
|
| The blockage of the high-affinity lysine binding sites of plasminogen by EACA significantly inhibits prourokinase-induced plasminogen activation. | 2002-04-29 |
|
| Spectrophotometric assays for L-lysine alpha-oxidase and gamma-glutamylamine cyclotransferase. | 2002-04-15 |
|
| Increase of sample load without peak deterioration by careful selection of electrolyte in capillary zone electrophoresis. | 2002-04-12 |
|
| Enhanced in vivo activity of peptidase-resistant analogs of the insect kinin neuropeptide family. | 2002-04 |
|
| Advances in the evaluation of the stability and characteristics of the amino acid and amine derivatives obtained with the o-phthaldialdehyde/3-mercaptopropionic acid and o-phthaldialdehyde/N-acetyl-L-cysteine reagents. High-performance liquid chromatography-mass spectrometry study. | 2002-03-08 |
|
| [Suppression of cytomegalovirus infection in cell system by fullerene amino acid derivates]. | 2002-02-21 |
|
| Effect of a synthetic carboxy-terminal peptide of alpha(2)-antiplasmin on urokinase-induced fibrinolysis. | 2002-02-01 |
|
| Antiapoptotic and proapoptotic action of various amino acids and analogs in starving MOLT-4 cells. | 2002-02-01 |
|
| Comparative analyses of the lysine binding site properties of apolipoprotein(a) kringle IV types 7 and 10. | 2002-01-29 |
|
| Solution structure of human apolipoprotein(a) kringle IV type 6. | 2002-01-15 |
|
| Enhancement of fibrinolytic activity of U937 cells by malformin A1. | 2002-01 |
|
| 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. | 2002-01 |
|
| The pharmacokinetics of epsilon-aminocaproic acid in children undergoing surgical repair of congenital heart defects. | 2002-01 |
|
| Central processing of plant volatiles in Agrotis ipsilon males is age-independent in contrast to sex pheromone processing. | 2002-01 |
|
| Light scattering and in vitro biocompatibility studies of poly (vinyl pyrrolidone) derivatives with amino-acid-dependent groups. | 2002 |
|
| Pharmacological strategies to decrease transfusion requirements in patients undergoing surgery. | 2002 |
|
| Renal complications of sickle cell disease: managing for optimal outcomes. | 2002 |
|
| Capillary electrophoresis/electrospray ion trap mass spectrometry for the analysis of negatively charged derivatized and underivatized glycans. | 2002 |
|
| Neuritogenesis and the nerve growth factor-induced differentiation of PC-12 cells requires annexin II-mediated plasmin generation. | 2001-12-28 |
|
| Two cases of fatal thrombosis after aminocaproic acid therapy and deep hypothermic circulatory arrest. | 2001-12 |
|
| Isolation, quantitation, and characterization of a stable complex formed by Lp[a] binding to triglyceride-rich lipoproteins. | 2001-12 |
|
| Pharmacologic preservation of the hemostatic system during cardiac surgery. | 2001-11 |
|
| Interaction of amorphous calcium phosphate with fibrin in vitro causes decreased fibrinolysis and altered protease profiles: implications for atherosclerotic disease. | 2001-10 |
|
| Black cutworm (Lepidoptera: Noctuidae) larval emigration and biomass in mixtures of endophytic perennial ryegrass and Kentucky bluegrass. | 2001-10 |
|
| Antifibrinolytic agents and desmopressin as hemostatic agents in cardiac surgery. | 2001-09 |
|
| Controls exerted by the Aib residue: helix formation and helix reversal. | 2001 |
|
| [Necrotizing myopathies]. | 2001 |
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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4321-58-8
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DTXSID80195786
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59010
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SUBSTANCE RECORD
