6-aminohexanoic acid

• ChemBase编号: 395
• 分子式: C6H13NO2
• 平均质量: 131.17292
• 单一同位素质量: 131.09462866
• SMILES: OC(=O)CCCCCN
• Canonical SMILES: NCCCCCC(=O)O
• InChI: InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
• InChIKey: SLXKOJJOQWFEFD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-aminohexanoic acid
• IUPAC传统名: 6-amino hexanoic acid; aminocaproic acid
• 商标名: Acepramin; Acepramine; Afibrin; Amicar; Amikar; Aminokapron; Atsemin; Caplamin; Capracid; Capramol; Capranol; Caprocid; Caprolisin; EACA; EACS; Epsamon; Epsicapron; Epsikapron; Epsilcapramin; Epsilcapramine; Hemocaprol; Hemopar; Hepin; Ipsilon; Respramin
• 别名: 6-氨基己酸; 6-氨己酸; ε-氨基己酸; 6-氨己酸; 6-氨基己酸; Aminocaproate; ACS; Aminocaproic; aminocaproic acid; ε-amino caproic acid; ε-Ahx; 6-aminohexanoic acid; E-aminocaproic acid; Aminocaproic Acid; 6-Amino-n-hexanoic acid; 6-Aminocaproic acid; EACA; ε-AMINO-n-CAPROIC ACID; ε-Aminocaproic acid; 6-Aminohexanoic acid solution; Additive Screening Solution 32/Fluka kit no 78374; 6-Aminohexanoic acid; A 14719; Acepramin; Acepramine; Acikaprin; Afibrin; Amikar; Aminokapron; CL 10304; CY 116; Caplamin; Capramol; Caprocid; Caprolisin; EACS; Epsamon; Epsicapron; Epsikapron; Epsilcapramin; Epsilon S; Hemocaprol; Hemopar; Hepin; Ipsilon; NSC 212532; NSC 26154; NSC 400230; Respramin; ε-Amino-n-caproic Acid; ε-Amino-n-hexanoic Acid; ε-Aminohexanoic Acid; ε-Leucine; ε-Norleucine; ω-Aminocaproic Acid; ω-Aminohexanoic Acid; 6-Aminohexanoic Acid; 6-Aminocaproic acid; Amicar; 6-Amino Hexanoic Acid; epsilon-Aminocaproic acid

登记号

• CAS号: 60-32-2
• EC号: 200-469-3
• MDL号: MFCD00008238
• Beilstein号: 906872
• 默克索引号: 14432
• PubChem SID: 46508972; 46506934; 160963858; 24890662; 24278238
• PubChem CID: 564

理论计算性质

JChem

• Acid pKa: 4.72614
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -2.050338
• LogD (pH = 7.4): -1.9963912
• Log P: -1.9971552
• 摩尔折射率: 34.6598 cm^3
• 极化性: 13.835553 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.69
• LOG S: -0.46
• 溶解度: 4.52e+01 g/l

分子性质

理化性质

• 溶解度: 5.05E+005 mg/L; H2O: soluble0.5 M, clear; H2O: soluble50 mg/mL; Water
• 外观: white powder; White Solid
• 熔点: 203-205°C; 204-206; 207-209 °C (dec.)(lit.); 210-212°C
• 密度: 1.03 g/mL at 20 °C
• 疏水性(logP): 0; -2.235

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: MO6300000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319; H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... PLG(5340); human ... PLG(5340)rat ... Ppm1a(24666)

产品相关信息

• 纯度: ≥98.5% (NT); ≥99%; ≥99% (titration); ≥99.0% g/mL; 95%; 98%; 99%
• 浓度: 1 M
• 级别: puriss.; SAJ special grade
• 成盐信息: Free Base
• 包装: vial of 200 mg
• 燃烧残渣: ≤0.1%
• 杂质: ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter
• 痕量阳离子: Al: ≤0.0005%; Ca: ≤0.005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.001%; Na: ≤0.02%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• 痕量阴离子: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• 线性分子式: H2N(CH2)5CO2H

详细说明

MP Biomedicals - 02101645

Crystalline
A plasmin inhibitor.

DrugBank - DB00513

• Drug Groups: approved; investigational
• Description: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]
• Indication: For use in the treatment of excessive postoperative bleeding.
• Pharmacology: 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.
• Toxicity: A few cases of acute overdosage with intravenous administration have been reported. The effects have ranged from no reaction to transient hypotension to severe acute renal failure leading to death. The intravenous and oral LD₅₀ were 3.0 and 12.0 g/kg respectively in the mouse and 3.2 and 16.4 g/kg respectively in the rat. An intravenous infusion dose of 2.3 g/kg was lethal in the dog.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: 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).
• Half Life: The terminal elimination half-life is approximately 2 hours.
• Elimination: Renal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.
• Distribution: * 23.1 ± 6.6 L
• Clearance: * 169 mL/min
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB04134

• Drug Groups: experimental
• Description: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]

Selleck Chemicals - S1671

Research Area: Cardiovascular Disease
Biological Activity:
Aminocaproic acid(Amicar) is a derivative and analogue of the amino acid lysine, which makes it an effective inhibitor for enzymes that binds particular residue. Such enzymes include proteolytic enzymes like plasmin, the enzyme is responsible for fibrinolysis. For this reason it is effective in treatment of certain bleeding disorders, especially fibrogenemia, and is marketed as Amicar. Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam. [1]

Sigma Aldrich - A2504

包装
1 kg in poly bottle
25, 100, 500 g in poly bottle
5 kg in poly drum
Application
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.
Biochem/physiol Actions
EACA is reported to inhibit chymotrypsin, Factor VIIa, lysine carbo-xy-peptidase, plasmin, and plasminogen activator.
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。据报告，EACA 可抑制纤溶酶原结合至活化的血小板。早期报告表明，EACA 可抑制补体系统第一组分的活化。结合并灭活羧肽酶 B。

Sigma Aldrich - A7824

Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告，EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明，EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5

Sigma Aldrich - A9812

包装
棕色螺纹盖样品瓶包装
Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告，EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明，EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5

Sigma Aldrich - A44606

Application
止血剂。2,6用作赖氨酸类似物，用于表征纤溶酶原中的结合位点。7,8
Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告，EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明，EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5

Sigma Aldrich - 07260

Other Notes
Improves solubilization of membrane proteins in electrophoresis6
Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告，EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明，EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5

Sigma Aldrich - 01-3540

Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告，EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明，EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5

Toronto Research Chemicals - A609985

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 electrophoresis. Studies suggest that 6-Aminohexanoic Acid i

参考文献

• Steffen, L.W., and Steffen, B.W., Clin. Chem. , 22 : 381, (1976).
• http://en.wikipedia.org/wiki/Aminocaproic_acid
• Ohta ,S. et al.: Chem. Pharm. Bull., 28, 1917 (1980)
• Shagger, H. et al.: Anal. Biochem., 199, 223 (1980)
• Soter, N.A. et al.: J. Immunol., 114, 928 (1980)
• Has been recommended as a reagent for the extraction of aldehydes from reaction mixtures, giving better recovery than bisulfite: Chem. Pharm. Bull., 28, 1917 (1980).