| Identification | More | [Name]
6-Aminocaproic acid | [CAS]
60-32-2 | [Synonyms]
6-AMINOCAPROIC ACID
6-AMINOHEXANOIC ACID
6-AMINO-N-CAPROIC ACID
6-AMINO-N-HEXANOIC ACID
6-L-AMINOHEXANOIC ACID
AMINOCAPROIC ACID
EACA
EPSILON-AMINOCAPROIC ACID
EPSILON-AMINO HEXANOIC ACID
EPSILON-AMINO-N-CAPROIC ACID
H-6-AHX-OH
H-ACP(6)-OH
H-ACP-OH
H-AHX(6)-OH
H-E-ACP-OH
H-EPSILON-ACP-OH
H-EPSILON-AHX-OH
H-EPSILON-AMINOCAPROIC ACID
NH2-(CH2)5-COOH
OMEGA-AMINOCAPROIC ACID | [EINECS(EC#)]
200-469-3 | [Molecular Formula]
C6H13NO2 | [MDL Number]
MFCD00008238 | [Molecular Weight]
131.17 | [MOL File]
60-32-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
207-209 °C (dec.) (lit.) | [Boiling point ]
242.49°C (rough estimate) | [density ]
1.03 g/mL at 20 °C
| [vapor pressure ]
<0.1 hPa (20 °C) | [refractive index ]
1.4870 (estimate) | [Fp ]
207-209°C | [storage temp. ]
2-8°C
| [solubility ]
H2O: 50 mg/mL
| [form ]
powder
| [pka]
4.373(at 25℃) | [color ]
white
| [Odor]
Odorless | [PH]
7.0-7.5 (50g/l, H2O, 20℃) | [Water Solubility ]
SOLUBLE | [Detection Methods]
T,NMR | [Merck ]
14,432 | [BRN ]
906872 | [InChIKey]
SLXKOJJOQWFEFD-UHFFFAOYSA-N | [LogP]
0.027 (est) | [CAS DataBase Reference]
60-32-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Hexanoic acid, 6-amino-(60-32-2) | [EPA Substance Registry System]
60-32-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
MO6300000
| [TSCA ]
Yes | [HS Code ]
29224995 | [Safety Profile]
Moderately toxic by intravenous route. Human systemic effects by ingestion: changes in tubules (includmg acute renal failure, acute tubular necrosis), hematuria, and increased body temperature. Experimental reproductive effects. An eye irritant. When heated to decomposition it emits toxic fumes such as NOx,. | [Hazardous Substances Data]
60-32-2(Hazardous Substances Data) | [Toxicity]
LD50 in rats (g/kg): 7.0 i.p.; ~3.3 i.v. (Hallesy) |
| Questions And Answer | Back Directory | [Description]
6-aminocaproic acid (Brand name: Amicar) is a kind of synthetic derivative of lysine. Since it is a analogue of amino acid lysine, it can act as the inhibitor for enzymes that need to bind to that particular lysine residue, e.g. the proteolytic enzyme such as plasmin, which is responsible for fibrinolysis. Therefore, it has anti-fibrinolytic activity. It also competitively inhibits activation of plasminogen, thereby reducing conversion of plasminogen to plasmin. Based on this property, it can be used for the treatment of acute bleeding due to elevated fibrinolytic activity in many clinical situations. It can also indicated by FDA for the prevention of recurrent hemorrhage in patients of traumatic hyphema. It may also act as a prophylactic against the vascular disease due to its inhibitory effect on the formation of lipoprotein which is the risk factor of vascular disease.
| [References]
https://pubchem.ncbi.nlm.nih.gov/compound/6-aminohexanoic_acid#section=Pharmacology-and-Biochemistry
https://en.wikipedia.org/wiki/Aminocaproic_acid
|
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Originator]
Epsilon,Roche,W. Germany,1962 | [Uses]
6-Aminohexanoic Acid is a reagent commonly used for the extraction of aldehydes from reaction mixtures. 6-Aminohexanoic Acid has also been shown to improve solubilization of membrane proteins in elect
rophoresis. Studies suggest that 6-Aminohexanoic Acid inhibits the activation of the first component of the complement system. | [Uses]
EACA is directly soluble in water at 25 mg/ml. As an inhibitor of plasmin it is has been utilized in the clotting buffer for fibrinogen assays. This buffer is 10 mM potassium and sodium phosphate, pH 6.4, with 0.20 g CaCl2, 5 g 6-Aminohexanoic acid, 1 g sodium azide, and 9 g NaCl in 1 liter. The buffer is stable indefinitely at room temperature. | [Uses]
hemostatic | [Uses]
Propylparaben Food preservative | [Application]
6-Aminohexanoic acid was used as a biochemical reagent. 6-Aminocaproic acid is used in organic synthesis. As an anti-fibrinolytic agent. Used as a hemostatic agent. 6-aminocaproic acid has a significant effect on some severe bleeding caused by increased fibrinolytic activity. It is suitable for oozing or local bleeding during various surgical operations. 6-aminocaproic acid is also used for hemoptysis, gastrointestinal bleeding and bleeding disorders in obstetrics and gynecology. 6-Aminocaproic acid works by inhibiting the fibrinolytic system. Mainly used for hemorrhage caused by elevated plasmin activity, such as obstetrics and gynecology hemorrhage, hemorrhage after prostate, liver, pancreas, lung and other visceral operations. Early intraoperative medication or preoperative medication can reduce intraoperative oozing and reduce blood transfusion volume.
6-Aminocaproic acid is an anti-fibrinolytic drug with a similar chemical structure to lysine. It can qualitatively inhibit the binding of plasminogen to fibrin and prevent its activation, thereby inhibiting fibrinolysis and achieving hemostasis. Aminocaproic acid is a monoaminocarboxylic acid, which can inhibit the conversion of plasminogen into plasmin and its binding to fibrin. For severe bleeding caused by hyperfibrinolysis caused by increased activation of plasminogen, can have therapeutic effect. | [Definition]
ChEBI: An amino-acid anion that is the conjugate base of 6-aminohexanoic acid. | [Preparation]
6-aminocaproic acid is obtained by hydrolysis of 6-(N-benzoylamino)capronitrile in the presence of hydrochloric acid, or by hydrolysis of caprolactam in the presence of hydrochloric acid, and then treated with ammonium hydroxide. | [Manufacturing Process]
5 kg of caprolactam were heated with 40 liters of water in a pressure vessel at 250°C for a period of four hours. These quantities of reactants correspond
to a water:lactam molecular ratio of 50:1. After cooling, the small quantity of
the nonsoluble substance that is formed is filtered off, and the filtrate is
evaporated as far as possible. The resulting concentrate is mixed with three
times its volume of strong alcohol, thereby causing the desired product,
epsilon-aminocaproic acid (6-aminohexanoic acid), to crystallize out. After
separating the crystalline product thus obtained, a further quantity of epsilonaminocaproic
acid can be obtained from the mother liquid if desired. | [Brand name]
Amicar (Xanodyne). | [Therapeutic Function]
Antifibrinolytic | [General Description]
Aminocaproic acid is a synthetic inhibitor of fibrinolysis and is utilized for the control of excessive bleeding in patients with amegakaryocytic thrombocytopenia.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. | [Biochem/physiol Actions]
Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis. Reported to inhibit plasminogen binding to activated platelets. An early report indicated that it inhibits the activation of the first component of the complement system. Binds and inactivates Carboxypeptidase B. | [Mechanism of action]
Because binding of plasminogen or plasmin to fibrinogen or fibrin is mediated by lysine
groups that are part of the structures of fibrin and fibrinogen, aminocaproic acid, which is
a structural analog of lysine that only differs in that it has one less amino group, acts as a
competitive inhibitor for binding of plasmin(ogen) to fibrin. Aminocaproic acid shifts the
homeostatic balance on the side of coagulation, thus restoring fibrinolytic mechanism
activity. Aminocaproic acid, which is not a procoagulant, such as those used during surgical
intervention and various pathological conditions, is accompanied by an elevation in fibrinolytic
activity of blood and tissue. It is used to stop bleeding. | [Synthesis]
Aminocaproic acid (24.4.1) is synthesized by hydrolyzing |? -caprolactam
at high temperature.
| [Veterinary Drugs and Treatments]
Aminocaproic acid has been used as a treatment to degenerative
myelopathy (seen primarily in German shepherds), but no controlled
studies documenting its efficacy were located. There is interest
in evaluating aminocaproic acid for adjunctive treatment of
thrombocytopenia in dogs, but efficacy and safety for this purpose
remains to be investigated. In humans, it is primarily used for treating
hyperfibrinolysis-induced hemorrhage. |
|
|