6-Aminocaproic acid, with an effective concentration of 61.5 μg/mL, inhibits fibrinolysis in Asian elephant plasma, ranging from 20-180 μg/mL [2]. 6-Using PEGylated indocyanine green, aminocaproic acid can be employed as a hydrophobic linker to enhance near-infrared fluorescence imaging and photothermal cancer therapy [4].

6-Aminocaproic acid (20-100 mg/kg; single oral dosage) reduces fibrinolysis at all levels studied in dogs [3]. 6-Aminocaproic acid (20-100 mg/kg; single oral dose) is rapidly absorbed (Tmax=1 hour) and rapidly excreted in dogs [3].

Absorption, Distribution and Excretion
Absorbed rapidly following oral administration. In adults, oral absorption appears to be a zero-order process with an absorption rate of 5.2 g/hr. The mean lag time in absorption is 10 minutes. After a single oral dose of 5 g, absorption was complete (F=1).
Renal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.
23.1 ± 6.6 L
169 mL/min
AMINOCAPROIC ACID IS WELL ABSORBED ORALLY... THIS DRUG IS EXCRETED RAPIDLY IN URINE, LARGELY UNCHANGED, & PEAK PLASMA LEVELS ARE OBTAINED ABOUT 2 HR AFTER A SINGLE ORAL DOSE.

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Metabolism / Metabolites
Sixty-five percent of the dose is recovered in the urine as unchanged drug and 11% of the dose appears as the metabolite adipic acid.

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Biological Half-Life
The terminal elimination half-life is approximately 2 hours.

Interactions
PLASMINOGEN ACTIVATORS SUCH AS STREPTOKINASE & UROKINASE ARE USED TO TREAT THROMBOEMBOLIC DISORDERS. ...AMINOCAPROIC ACID COUNTERACTS THE THROMBOLYTIC EFFECT OF THESE DRUGS...

[1]. Epsilon-aminocaproic acid (EACA). Semin Thromb Hemost. Summer 1978;5(1):27-40.

[2]. EFFECT OF ε-AMINOCAPROIC ACID ON FIBRINOLYSIS IN PLASMA OF ASIAN ELEPHANTS (ELEPHAS MAXIMUS). J Zoo Wildl Med. 2016 Jun;47(2):397-404.

[3]. Effect of aminocaproic acid on clot strength and clot lysis of canine blood determined by use of an in vitro model of hyperfibrinolysis. Am J Vet Res. 2016 Nov;77(11):1258-1265.

[4]. 6-Aminocaproic acid as a linker to improve near-infrared fluorescence imaging and photothermal cancer therapy of PEGylated indocyanine green. Colloids Surf B Biointerfaces. 2021 Jan;197:111372.

6-aminohexanoic acid is an epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator. It has a role as an antifibrinolytic drug, a hematologic agent and a metabolite. It is an epsilon-amino acid and an omega-amino fatty acid. It is functionally related to a hexanoic acid. It is a conjugate acid of a 6-aminohexanoate. It is a tautomer of a 6-aminohexanoic acid zwitterion.
An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.
Aminocaproic acid is an Antifibrinolytic Agent. The physiologic effect of aminocaproic acid is by means of Decreased Fibrinolysis.
Aminocaproic acid has been reported in Daphnia pulex, Arabidopsis thaliana, and other organisms with data available.
Aminocaproic Acid is a synthetic lysine derivative with antifibrinolytic activity. Aminocaproic acid competitively inhibits activation of plasminogen, thereby reducing conversion of plasminogen to plasmin (fibrinolysin), an enzyme that degrades fibrin clots as well as fibrinogen and other plasma proteins including the procoagulant factors V and VIII. Aminocaproic acid competitively reduces the conversion of plasminogen to plasmin by plasminogen activators. It directly inhibits proteolytic activity of plasmin, but higher doses are required than are needed to reduce plasmin formation. Aminocaproic acid is used in the treatment of hemorrhage and prophylactically against hemorrhage, including hyperfibrinolysis-induced hemorrhage and postsurgical hemorrhage.
An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.

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Drug Indication
For use in the treatment of excessive postoperative bleeding.
FDA Label

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Mechanism of Action
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. This consequently will reduce the amount of bleeding post surgery. Elevated plasma levels of lipoprotein(a) have been shown to increase the risk of vascular disease. Lipoprotein 9a)a has two components, apolipoprotein B-100, linked to apolipoprotein (a). Aminocaproic acid may change the conformation of apoliprotein (a), changing its binding properties and potentially preventing the formation of lipoprotein (a).
A COMPETITIVE INHIBITOR OF ACTIVATORS OF PROFIBRINOLYSIN &, TO LESSER EXTENT, OF FIBRINOLYSIN. AS A CONSEQUENCE, IT SUPPRESSES FORMATION OF FIBRINOLYSIN, AN ENZYME WHICH DESTROYS FIBRINOGEN, FIBRIN, & OTHER CLOTTING COMPONENTS.
MICROCALORIMETRY AND UV AND IR SPECTROSCOPY WERE USED TO STUDY THE INTERMOLECULAR INTERACTIONS OF PLASMINOGEN AND PLASMIN WITH EPSILON-AMINOCAPROIC ACID (I) TO DETERMINE THE MECHANISM OF FIBRINOLYSIS INHIBITION. AT LOW DOSES, THE INHIBITORY EFFECT WAS DUE MAINLY TO BLOCKADE OF THE STAGE OF ACTIVATION OF PLASMINOGEN, WHEREAS THE EFFECTIVENESS OF HIGH CONCENTRATIONS OF I WAS ACHIEVED ALSO BY INACTIVATION OF THE ENZYMIC ACTIVITY OF PLASMIN.

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Therapeutic Uses
Antifibrinolytic Agents
...USED IN TREATMENT OF PROCEDURES OR DISORDERS IN WHICH FIBRINOLYSIS IS ENHANCED...CARDIAC BYPASS, POSTCAVAL SHUNT, MAJOR THORACIC SURGERY, PROSTATIC POSTOPERATIVE HEMATURIA...NONSURGICAL HEMATURIA, LEUKEMIA, METASTATIC PROSTATIC CARCINOMA, CIRRHOSIS & OTHER HEPATIC DISEASES, ECLAMPSIA, INTRAUTERINE FETAL DEATH, AMNIOTIC FLUID EMBOLISM & ABRUPTIO PLACENTAE. THE DRUG IS OF NO VALUE IN HEMORRHAGE DUE TO THROMBOCYTOPENIA, HYPERHEPARINEMIA, OR OTHER COAGULATION DEFECTS, OR TO VASCULAR DISRUPTION.
FOR IV ADMIN...SHOULD BE DILUTED IN ISOTONIC OR DEXTROSE SOLN & INJECTED SLOWLY. AFTER 8 HR TREATMENT, PATIENT'S CONDITION SHOULD BE REEVALUATED.
...SPECIFIC ANTIDOTE FOR AN OVERDOSE OF A FIBRINOLYTIC AGENT. ...
For more Therapeutic Uses (Complete) data for 6-AMINOCAPROIC ACID (9 total), please visit the HSDB record page.

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Drug Warnings
RAPID IV ADMIN SHOULD BE AVOIDED TO PREVENT HYPOTENSION, BRADYCARDIA, & OTHER ARRHYTHMIAS.
...TERATOGENIC IN ANIMALS & HENCE SHOULD NOT BE USED IN HUMANS IN FIRST 2 TRIMESTERS OF PREGNANCY & IN THIRD TRIMESTER ONLY IF ITS USE IS IMPERATIVE.
IF AMINOCAPROIC ACID IS GIVEN TO PT WITH DIC /DIFFUSE INTRAVASCULAR COAGULATION/ IT MAY CAUSE SERIOUS OR EVEN FATAL THROMBUS FORMATION. ...MOST EXPERTS DO NOT USE AMINOCAPROIC ACID TO TREAT "FIBRINOLYTIC" HEMORRHAGE UNLESS THERE IS DEFINITIVE PROOF THAT DIC IS NOT THE UNDERLYING CAUSE.
WHEN AMINOCAPROIC ACID IS GIVEN DURING SURGERY, CARE MUST BE TAKEN TO FREE THE BODY CAVITIES OF BLOOD CLOTS SINCE THE DRUG REMAINS IN HIGH CONCN IN THE CLOTS, THEREBY INHIBITING THEIR PHYSIOLOGIC DISSOLUTION.
INCIDENCE OF THROMBOTIC EVENTS SECONDARY TO INHIBITION OF FIBRINOLYTIC SYSTEM BY DRUG IS UNKNOWN, BUT MAY BE PARTICULARLY INCR IN PT WITH UNDERLYING PREDISPOSITION TO DEVELOP THROMBOSIS.

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Pharmacodynamics
Aminocaproic acid works as an antifibrinolytic. It is a derivative of the amino acid lysine. The fibrinolysis-inhibitory effects of aminocaproic acid appear to be exerted principally via inhibition of plasminogen activators and to a lesser degree through antiplasmin activity. Aminocaproic acid may be a possible prophylactic for vascular disease, as it may prevent formation of lipoprotein (a), a risk factor for vascular disease.

C6H13NO2

131.1729

131.094

60-32-2

6-Aminocaproic acid-d6;1228656-08-3;6-Aminocaproic acid hydrochloride;4321-58-8;6-Aminocaproic acid-d10;461432-51-9

564

White to off-white solid powder

1.0±0.1 g/cm3

255.6±23.0 °C at 760 mmHg

207-209 °C (dec.)(lit.)

108.4±22.6 °C

0.0±1.1 mmHg at 25°C

1.467

-0.11

2

3

5

9

83.1

0

SLXKOJJOQWFEFD-UHFFFAOYSA-N

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

6-aminohexanoic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ≥ 50 mg/mL (~381.18 mM)
DMSO : ~1 mg/mL (~7.62 mM)

Solubility in Formulation 1: 25 mg/mL (190.59 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)