6-Aminohexanoic Acid

FINE, WHITE, CRYSTALLINE POWDER

LEAVES FROM ETHER

1 G IN 3 ML OF WATER; SLIGHTLY SOL IN ALCOHOL; PRACTICALLY INSOL IN CHLOROFORM & ETHER

505.0 mg/mL at 25 °C

0.9 [ug/mL] (The mean of the results at pH 7.4)

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

202-203 °C

205 °C

Wet Solid

White solid; [HSDB] White crystalline solid; [MSDSonline]

Solid

This chemical does not meet GHS hazard criteria for 78.6% (206 of 262) of all reports.

Warning

H315 (20.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 262 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Hexanoic acid, 6-amino-

Hexanoic acid, 6-amino- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanoic acid, 6-amino- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/22890

Hexanoic acid, 6-amino-: Does not have an individual approval but may be used under an appropriate group standard

Possible side effects in long-term therapy greater than 2 weeks include seizures, myopathy, renal failure, and kidney failure; [HSDB] May cause irritation; Effects in high-dose animal studies include convulsions or effect on seizure threshold and changes in the renal tubules; [MSDSonline] Not teratogenic in rabbits; [REPROTOX]

REVIEW: A PROFILE OF THE PHARMACOLOGY, THERAPEUTIC INDICATIONS, THE PREPARATIONS AND STRENGTHS AVAILABLE, THE DOSAGE, CONTRAINDICATIONS, TOXICITY, INTERACTIONS, PHARMACOKINETICS AND OTHER PHYSICAL PROPERTIES OF EPSILON-AMINOCAPROIC ACID.[PROFILE ON EPSILON AMINOCAPROIC ACID; AUST J PHARM 62(JUN) 403 (1981)]

Neurotoxin - Other CNS neurotoxin

Although aminocaproic acid is generally well tolerated in patients, reported adverse effects of the drug include malaise, myalgias, renal impairment, seizures, hypotension, bradycardia, thrombosis, edemas, and injection site reactions. Less frequently, aminocaproic acid may also lead to gastrointestinal symptoms, such as nausea and diarrhea. In addition, there have been reports of nasal congestion and conjunctival suffusion with the usage of aminocaproic acid.

Aminocaproic acid is associated with a low acute toxicity risk. Research on teratogenic in vitro studies has revealed no fetal abnormalities when administering aminocaproic acid dosages up to 5000 mcg/kg/d. Retinal changes have been reported in dogs after receiving aminocaproic acid orally over 1 year at doses approximately 7 times higher than the maximum recommended dose for in vivo use. A significant concern regarding aminocaproic acid treatment is whether this drug can increase patients' risk of thrombosis and intravascular coagulation. Although there are isolated reports of arterial or venous thrombosis, it is noteworthy that the underlying thrombotic comorbidity is present in each reported case.

CARDIAC & HEPATIC NECROSES WERE FOUND @ POSTMORTEM EXAMINATION IN ONE PT WHO HAD RECEIVED THERAPEUTIC DOSES OF THE DRUG.

AMINOCAPROIC ACID MAY CAUSE ITCHING, ERYTHEMA, SKIN RASH, DIURESIS, HEARTBURN, NAUSEA, & DIARRHEA. ...HAS ANTIADRENERGIC EFFECT SIMILAR TO GUANETHIDINE, SO THAT NASAL STUFFINESS, CONJUNCTIVAL SUFFUSION, & HYPOTENSION MAY OCCUR. ...MAY ENHANCE THROMBOTIC PROCESSES BY SUPPRESSION OF REACTIVE FIBRINOLYSIS...

AMICAR HAS BEEN USED IN SUBARACHNOID HEMORRHAGE TO PROMOTE CLOTTING, BUT CEREBRAL THROMBOSIS HAS BEEN REPORTED IN VARIOUS VASCULAR COMPARTMENTS FOLLOWING ITS USE. TWO PATIENTS ARE DESCRIBED WHO HAD CEREBRAL ANGIOGRAPHY AFTER AMICAR THERAPY WHICH DEMONSTRATED THROMBOSIS UNRELATED TO VASCULAR SPASM OR TO TECHNICAL COMPLICATIONS OF ANGIOGRAPHY.

Drug Induced Liver Injury Rank (DILIrank 2.0)

Aminocaproic acid

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

/AMINOCAPROIC ACID/...IS TERATOGENIC IN ANIMALS...

SUBENDOCARDIAL HEMORRHAGES & MYOCARDIAL DEPRESSION HAVE BEEN ASSOCIATED WITH ADMIN OF AMINOCAPROIC ACID IN SEVERAL ANIMAL SPECIES. DRUG MAY TRANSIENTLY ALTER PROTEIN METABOLISM BY INHIBITING UTILIZATION OF LYSINE.

...WHEN GIVEN IV TO CATS HAS SYMPATHOMIMETIC EFFECTS, INCL DILATED PUPILS & EXOPHTHALMOS ATTRIBUTABLE PARTLY TO RELEASE OF CATECHOLAMINES. ...CHRONICALLY BY MOUTH IT OCCASIONALLY CAUSES NASAL CONGESTION & CONJUNCTIVAL HYPEREMIA.

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.

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.

U6F3787206

AMINOCAPROIC ACID

Established Pharmacologic Class [EPC] - Antifibrinolytic Agent

Physiologic Effects [PE] - Decreased Fibrinolysis

Aminocaproic acid is an Antifibrinolytic Agent. The physiologic effect of aminocaproic acid is by means of Decreased Fibrinolysis.

AMINOCAPROIC ACID

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.

Used as a captive chemical intermediate in the production of nylon 6; [HSDB] Used as a hemostatic; [Merck Index] An inhibitor of fibrinolysis and sold as Amicar; [REPROTOX]

ANTIDOTE FOR OVERDOSAGE IN FIBRINOLYTIC THERAPY; CAPTIVE CHEM INT IN PRODUCTION OF NYLON 6

MEDICATION

MEDICATION (VET):

(1972) No Data

(1975) No Data

(1975) 3.8X10+6 GRAMS (PRINCPL CUSTMS DISTS)

(1976) 5.50X10+6 GRAMS (PRINCPL CUSTMS DISTS)

2023: 50,000 - <250,000 lb

(1974) GREATER THAN 4.54X10+5 GRAMS

(1975) No Data

HEATING OF AN AQUEOUS SOLUTION OF CAPROLACTAM WITH CALCIUM HYDROXIDE TO GIVE CALCIUM AMINOCAPROATE, FOLLOWED BY REACTION WITH SULFURIC ACID

...FROM EPSILON-BENZOYLAMINOCAPRONITRILE: RUZICKA, HUGOSON, HELV CHIM ACTA 4, 472 (1921); FROM EPSILON CAPROLACTAM...SULZBACHER, MFR CHEMIST 33, 463 (1963); FROM 1-HYDROXYCYCLOHEXYLHYDROPEROXIDE: MINISCI, PORTOLANI; GAZZ CHIM ITAL 89, 1941 (1959).

All Other Basic Organic Chemical Manufacturing

Hexanoic acid, 6-amino-: ACTIVE