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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
Structure of AMINOCAPROIC ACID

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)

HIDE SMILES / InChI

Description
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

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
0.009 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

1981
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
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)
Cardiac disorder NOS (1 patient)
Hepatic lesion (1 patient)
Sources: Page: p.6
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: 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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Controls exerted by the Aib residue: helix formation and helix reversal.
2001
Anti-fibrinolytic use for minimising perioperative allogeneic blood transfusion.
2001
Utilization of technologies to reduce allogeneic blood transfusion in the United States.
2001 Apr
Transcriptional induction of diverse midgut trypsins in larval Agrotis ipsilon and Helicoverpa zea feeding on the soybean trypsin inhibitor.
2001 Apr 27
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
Postoperatively administered aprotinin or epsilon aminocaproic acid after cardiopulmonary bypass has limited benefit.
2001 Aug
Design, synthesis, and biological evaluation of HIV/FIV protease inhibitors incorporating a conformationally constrained macrocycle with a small P3' residue.
2001 Jan 22
Establishment and characterization of insect cell lines from 10 lepidopteran species.
2001 Jun
Comparison of epsilon aminocaproic acid and low-dose aprotinin in cardiopulmonary bypass: efficiency, safety and cost.
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
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
Antifibrinolytic agents and desmopressin as hemostatic agents in cardiac surgery.
2001 Sep
Ophthalmic surgery in haemophilia.
2001 Sep
Light scattering and in vitro biocompatibility studies of poly (vinyl pyrrolidone) derivatives with amino-acid-dependent groups.
2002
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
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
Increasing paracellular porosity by E-cadherin peptides: discovery of bulge and groove regions in the EC1-domain of E-cadherin.
2002 Aug
Effect of a synthetic carboxy-terminal peptide of alpha(2)-antiplasmin on urokinase-induced fibrinolysis.
2002 Feb 1
Enhancement of fibrinolytic activity of U937 cells by malformin A1.
2002 Jan
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
Clinical management of hereditary angio-oedema in children.
2002 Jun
Nitric oxide: platelet protectant properties during cardiopulmonary bypass/ECMO.
2002 Jun
Evidence-based EACA dosing?
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
Fibrin as an alternative biopolymer to type-I collagen for the fabrication of a media equivalent.
2002 Jun 15
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
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 [USP MONOGRAPH]
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
CL-10304
Code English
AMINOCAPROIC ACID [EP IMPURITY]
Common Name English
ZINC ACEXAMATE IMPURITY B [EP IMPURITY]
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
EPSILON-AMINOCAPROIC ACID
JAN  
Systematic Name English
Aminocaproic acid [WHO-DD]
Common Name English
aminocaproic acid [INN]
Common Name English
EACA
Code English
CL 10304
Code English
Classification Tree Code System Code
NCI_THESAURUS C78311
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LIVERTOX 39
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FDA ORPHAN DRUG 83294
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WHO-ATC B02AA01
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NDF-RT N0000175632
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NDF-RT N0000175634
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NDF-RT N0000175632
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Code System Code Type Description
RS_ITEM_NUM
1021000
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PRIMARY
SMS_ID
100000091891
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PRIMARY
EPA CompTox
DTXSID0020070
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PRIMARY
CHEBI
16586
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PRIMARY
DAILYMED
U6F3787206
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PRIMARY
ECHA (EC/EINECS)
200-469-3
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PRIMARY
HSDB
3005
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PRIMARY
WIKIPEDIA
AMINOCAPROIC ACID
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PRIMARY
NCI_THESAURUS
C47391
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PRIMARY
EVMPD
SUB05438MIG
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PRIMARY
NSC
400230
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PRIMARY
IUPHAR
6574
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PRIMARY
DRUG CENTRAL
163
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PRIMARY
ChEMBL
CHEMBL1046
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PRIMARY
MESH
D015119
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PRIMARY
FDA UNII
U6F3787206
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PRIMARY
INN
1189
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PRIMARY
MERCK INDEX
m1697
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PRIMARY Merck Index
DRUG BANK
DB00513
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PRIMARY
RXCUI
113373
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ALTERNATIVE
PUBCHEM
564
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PRIMARY
RXCUI
99
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PRIMARY
NSC
26154
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PRIMARY
CAS
60-32-2
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PRIMARY