6-Aminohexanoic Acid
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Grundinformationen
- CAS
1319-82-0- Standard-SMILES
NCCCCCC(=O)O- InChIKey
SLXKOJJOQWFEFD-UHFFFAOYSA-N- Summenformel
- C6H13NO2
- Durchschnittliche Molmasse
- 131,17 g/mol
- Monoisotopische Masse
- 131,09462866
Überblick
6-aminohexanoic acid is an -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 a metabolite, an antifibrinolytic drug and a hematologic agent. 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.
Namen und Bezeichner
- Bevorzugter Name
- 6-Aminohexanoic Acid
- IUPAC
- 6-aminohexanoic acid
- Englischer Name
- Aminocaproic Acid
- Summenformel
- C6H13NO2
- Molmasse
- 0
Namen und Synonyme
6-aminohexanoic acid6-Aminocaproic acidaminocaproic acid60-32-2Hexanoic acid, 6-amino-AcepramineEpsicapronEpsilcapraminCapramolCaprolisinAcepraminHemopar
Weitere Namen anzeigen
Aminohexanoic acidAcido aminocaproicoAcidum aminocaproicumHexanoic acid, amino-Aminohexanoic acid USP/EP/BPAcidum aminocaproicum [inn-latin]Acido aminocaproico [inn-spanish]Acide aminocaproique [inn-french]
IpsilonRespraminAmikarEACAAminokapronAfibrinCaplaminAtsemin
Datenbank-Bezeichner
- CAS
1319-82-0、60-32-2- PubChem CID
- 564
- DTXSID
DTXSID0020070- ChEMBL
CHEMBL1046
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- -3
- Polarare Oberfläche (TPSA)
- 63,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 83,1
Experimentelle und physikochemische Eigenschaften
Chemical ClassesNitrogen Compounds -> Amino Carboxylic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110]
LogP-2.95
OdorODORLESS, OR NEARLY SO
TasteTASTELESS
Color/Form
FINE, WHITE, CRYSTALLINE POWDER
LEAVES FROM ETHER
Solubility
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)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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.
Gefahrenhinweise
Regulatory Information
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
Other Safety InformationIMAP assessments - Hexanoic acid, 6-amino-: Environment tier I assessment
Hazards Summary
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]
Special Reports
Chemie und Industrie
Pharmakologische Informationen
ATC CodeB - Blood and blood forming organs
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.
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.
Biological Half-LifeThe terminal elimination half-life is approximately 2 hours.
Metabolism/MetabolitesSixty-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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