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Details

Stereochemistry ACHIRAL
Molecular Formula C6H13NO2
Molecular Weight 131.1732
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINOCAPROIC ACID

SMILES

C(CCC(=O)O)CCN

InChI

InChIKey=SLXKOJJOQWFEFD-UHFFFAOYSA-N
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)

HIDE SMILES / InChI

Description
Curator's Comment:: 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

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

Targets

Primary TargetPharmacologyConditionPotency
0.00899999999999999932 mM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
AMICAR

Approved Use

AMICAR 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 Date

378604800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 50-74
Sex: M+F
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:
unhealthy
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
Disc. AE: Cerebellar hemorrhage, Cardiac disorder NOS...
AEs leading to
discontinuation/dose reduction:
Cerebellar hemorrhage (grade 5, 1 patient)
Cardiac disorder NOS (1 patient)
Hepatic lesion (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
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
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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Seizure after infusion of aminocaproic acid.
1978 Nov 24
Development of an improved medium for germination of Cajanus cajan (L.) Millsp. pollen in vitro.
2001 Apr
Binding of recombinant apolipoprotein(a) to human platelets and effect on platelet aggregation.
2001 Apr
Utilization of technologies to reduce allogeneic blood transfusion in the United States.
2001 Apr
Effect of progressive benzyl substitution on the conformations of aminocaproic acid-cyclized dipeptides.
2001 Apr 20
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
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
Postoperatively administered aprotinin or epsilon aminocaproic acid after cardiopulmonary bypass has limited benefit.
2001 Aug
Analysis of amide bond formation with an alpha-hydroxy-beta-amino acid derivative, 3-amino-2-hydroxy-4-phenylbutanoic acid, as an acyl component: byproduction of homobislactone.
2001 Aug 10
Classical and slow-binding inhibitors of human type II arginase.
2001 Aug 7
Neuritogenesis and the nerve growth factor-induced differentiation of PC-12 cells requires annexin II-mediated plasmin generation.
2001 Dec 28
Diagnosis of mastocytosis: value of cytochemistry and immunohistochemistry.
2001 Jul
Establishment and characterization of insect cell lines from 10 lepidopteran species.
2001 Jun
Gender does not influence epsilon-aminocaproic acid concentrations in adults undergoing cardiopulmonary bypass.
2001 Jun
Evaluation of a new point of care heparin test for cardiopulmonary bypass: the TAS heparin management test.
2001 Mar
Synthesis of biotinylated bis(D-glucose) derivatives for glucose transporter photoaffinity labelling.
2001 Mar 22
Reaction of canine plasminogen with 6-aminohexanoate: a thermodynamic study combining fluorescence, circular dichroism, and isothermal titration calorimetry.
2001 Mar 27
Effect of epsilon-aminocaproylaminoacids on the activity of proteolytic enzymes.
2001 Mar-Apr
Plasma proteinase inhibitor activity and hemostasis tests in children with nephrotic syndrome. Effect of prednisone alone and prednisone plus epsilon-aminocaproic acid treatment regimens: a preliminary report.
2001 Mar-Apr
Pharmacologic preservation of the hemostatic system during cardiac surgery.
2001 Nov
Increase in bone growth factors with healing rat fractures: the enhancing effect of zinc.
2001 Oct
Antifibrinolytic agents and desmopressin as hemostatic agents in cardiac surgery.
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
Light scattering and in vitro biocompatibility studies of poly (vinyl pyrrolidone) derivatives with amino-acid-dependent groups.
2002
Capillary electrophoresis/electrospray ion trap mass spectrometry for the analysis of negatively charged derivatized and underivatized glycans.
2002
Enhanced in vivo activity of peptidase-resistant analogs of the insect kinin neuropeptide family.
2002 Apr
Increase of sample load without peak deterioration by careful selection of electrolyte in capillary zone electrophoresis.
2002 Apr 12
Spectrophotometric assays for L-lysine alpha-oxidase and gamma-glutamylamine cyclotransferase.
2002 Apr 15
[Macroscopic hematuria associated with sickle cell anemia trait: report of ten cases].
2002 Aug
Antiapoptotic and proapoptotic action of various amino acids and analogs in starving MOLT-4 cells.
2002 Feb 1
The pharmacokinetics of epsilon-aminocaproic acid in children undergoing surgical repair of congenital heart defects.
2002 Jan
Central processing of plant volatiles in Agrotis ipsilon males is age-independent in contrast to sex pheromone processing.
2002 Jan
Comparative analyses of the lysine binding site properties of apolipoprotein(a) kringle IV types 7 and 10.
2002 Jan 29
Epsilon-aminocaproic acid and renal complications: case report and review of the literature.
2002 Jul
Clinical management of hereditary angio-oedema in children.
2002 Jun
The effect of 6-aminohexanoic acid and fucoidan on the activation of glutamic plasminogen by streptokinase.
2002 Jun
Tissue factor is the receptor for plasminogen type 1 on 1-LN human prostate cancer cells.
2002 Jun 15
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 Mar 8
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
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 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.
Name Type Language
AMINOCAPROIC ACID
EP   HSDB   INN   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
177-JD
Code English
.EPSILON.-AMINOCAPROIC ACID
JAN   MI  
Systematic Name English
6-AMINOHEXANOIC ACID
Systematic Name English
AMINOCAPROIC ACID [WHO-DD]
Common Name English
AMINOCAPROIC ACID [VANDF]
Common Name English
.EPSILON.-AMINOCAPROIC ACID [MI]
Common Name English
AMINOCAPROIC ACID [EP MONOGRAPH]
Common Name English
AMINOCAPROIC ACID [USP-RS]
Common Name English
.EPSILON.-AMINOCAPROIC ACID [JAN]
Common Name English
177 J.D.
Code English
EPSILON-AMINOCAPROIC ACID [JAN]
Common Name English
HEXANOIC ACID, 6-AMINO-
Common Name English
AMINOCAPROIC ACID [ORANGE BOOK]
Common Name English
EPSILON AMINOCAPROIC ACID
Systematic Name English
177 JD
Code English
AMINOCAPROIC ACID [MART.]
Common Name English
AMINOHEXANOIC ACID
Systematic Name English
NSC-26154
Code English
AMINOCAPROIC ACID [EP]
Common Name English
CL-10304
Code English
ZINC ACEXAMATE IMPURITY B [EP]
Common Name English
AMINOCAPROIC ACID [HSDB]
Common Name English
6-AMINOCAPROIC ACID [INCI]
Common Name English
AMICAR
Brand Name English
CY-116
Code English
NSC-400230
Code English
AMINOCAPROIC ACID [USAN]
Common Name English
EPSILCAPRAMIN
Common Name English
6-AMINOCAPROIC ACID
INCI  
INCI  
Official Name English
AMINOCAPROIC ACID [USP]
Common Name English
EPSILON-AMINOCAPROIC ACID
JAN  
Systematic Name English
AMINOCAPROIC ACID [INN]
Common Name English
EACA
Code English
CL 10304
Code English
Classification Tree Code System Code
NCI_THESAURUS C78311
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
LIVERTOX 39
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
FDA ORPHAN DRUG 83294
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
WHO-ATC B02AA01
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
NDF-RT N0000175632
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
NDF-RT N0000175634
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
NDF-RT N0000175632
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
Code System Code Type Description
USP_CATALOG
1021000
Created by admin on Fri Jun 25 21:10:44 UTC 2021 , Edited by admin on Fri Jun 25 21:10:44 UTC 2021
PRIMARY USP-RS
EPA CompTox
60-32-2
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-469-3
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PRIMARY
HSDB
3005
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY
WIKIPEDIA
AMINOCAPROIC ACID
Created by admin on Fri Jun 25 21:10:44 UTC 2021 , Edited by admin on Fri Jun 25 21:10:44 UTC 2021
PRIMARY
NCI_THESAURUS
C47391
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PRIMARY
EVMPD
SUB05438MIG
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PRIMARY
IUPHAR
6574
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PRIMARY
DRUG CENTRAL
163
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PRIMARY
ChEMBL
CHEMBL1046
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY
MESH
D015119
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PRIMARY
FDA UNII
U6F3787206
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY
INN
1189
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PRIMARY
MERCK INDEX
M1697
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00513
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY
RXCUI
113373
Created by admin on Fri Jun 25 21:10:44 UTC 2021 , Edited by admin on Fri Jun 25 21:10:44 UTC 2021
ALTERNATIVE
PUBCHEM
564
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY
RXCUI
99
Created by admin on Fri Jun 25 21:10:44 UTC 2021 , Edited by admin on Fri Jun 25 21:10:44 UTC 2021
PRIMARY
CAS
60-32-2
Created by admin on Fri Jun 25 21:10:43 UTC 2021 , Edited by admin on Fri Jun 25 21:10:43 UTC 2021
PRIMARY