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N-アセチル-L-システイン

N-アセチル-L-システイン 化学構造式
616-91-1
CAS番号.
616-91-1
化学名:
N-アセチル-L-システイン
别名:
N-アセチル-L-システイン;パルボレックス;ムコフィリン;(R)-3-メルカプト-2-(アセチルアミノ)プロピオン酸;フルイムシル;ナシステリン;ブロンコリシン;N-アセチル-L-Cys-OH;サテリット;アセチルシステイン;Nα-アセチルシステイン;レスパイル;ムコソルビン;N-アセチルシステイン;(R)-2-(アセチルアミノ)-3-メルカプトプロピオン酸;アセテイン;アイルブロン;(2R)-2-(アセチルアミノ)-3-メルカプトプロピオン酸;フルイムセチン;ムコリチクム-ラッペ
英語化学名:
N-Acetyl-L-cysteine
英語别名:
ACC;LNAL;LNAC;ACC1;ACACA;Brunac;Fabrol;Inspir;NAC-TB;Tixair
CBNumber:
CB2127503
化学式:
C5H9NO3S
分子量:
163.19
MOL File:
616-91-1.mol

N-アセチル-L-システイン 物理性質

融点 :
106-108 °C(lit.)
比旋光度 :
-35.1 ºC (c=2,H2O)
比重(密度) :
1.249 (estimate)
屈折率 :
24 ° (C=JPC Method)
貯蔵温度 :
2-8°C
溶解性:
H2O: 100 mg/mL with heating
外見 :
Solid
酸解離定数(Pka):
pK1: 9.52 (30°C)
色:
White
水溶解度 :
Soluble in water, ethanol, methanol, dimethyl sulfoxide, hot isopropyl alcohol, methyl acetate and ethyl acetate. Insoluble in chloroform and ether.
Merck :
14,88
BRN :
1724426
安定性::
Stable. Incompatible with strong oxidizing agents.
InChIKey:
PWKSKIMOESPYIA-BYPYZUCNSA-N
CAS データベース:
616-91-1(CAS DataBase Reference)
NISTの化学物質情報:
Acetylcysteine(616-91-1)
EPAの化学物質情報:
L-Cysteine, N-acetyl-(616-91-1)

安全性情報

Rフレーズ  36/37/38
Sフレーズ  22-24/25
WGK Germany  3
RTECS 番号 HA1660000
10-23
TSCA  Yes
HSコード  29309016
有毒物質データの 616-91-1(Hazardous Substances Data)
毒性 LD50 orally in rats: 5050 mg/kg (Goldenthal)
化審法 (2)-2757

N-アセチル-L-システイン 価格 もっと(46)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01FLC003631 N-アセチル-L-システイン
N-Acetyl-l-cysteine
616-91-1 25g ¥6600 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01FLC003631 N-アセチル-L-システイン
N-Acetyl-l-cysteine
616-91-1 100g ¥14500 2018-12-26 購入
東京化成工業 A0905 N-アセチル-L-システイン >98.0%(HPLC)(T)
N-Acetyl-L-cysteine >98.0%(HPLC)(T)
616-91-1 250g ¥25700 2018-12-04 購入
東京化成工業 A0905 N-アセチル-L-システイン >98.0%(HPLC)(T)
N-Acetyl-L-cysteine >98.0%(HPLC)(T)
616-91-1 25g ¥4600 2018-12-04 購入
関東化学株式会社(KANTO) 01763-30 N‐アセチル‐L(+)‐システイン >98.0%(T)
N‐Acetyl‐L(+)‐cysteine >98.0%(T)
616-91-1 25g ¥5200 2018-12-13 購入

N-アセチル-L-システイン MSDS


N-Acetyl-L-(+)-cysteine

N-アセチル-L-システイン 化学特性,用途語,生産方法

外観

白色, 結晶~結晶性粉末

定義

本品は、システイン(*)をアセチル化したものであり、次の化学式で表される。
参照表示名称:システイン

溶解性

水、エタノール及びアセトンにやや溶けやすい。

用途

SH 基を有する化合物です。 粘液ムコタンパクのジスルフィド結合を解離 する作用を示します。

用途

SH 基を有する化合物です。 粘液ムコタンパクのジスルフィド結合を解離 する作用を示します。

化粧品の成分用途

皮膚コンディショニング剤、酸化防止剤

効能

解毒薬 (アセトアミノフェン), 粘液溶解薬

商品名

アセチルシステイン (あゆみ製薬); ムコフィリン (サンノーバ)

説明

N-acetylcysteine amide is a kind of membrane penetrating antioxidant. It has anti-inflammatory activity through regulating the activation of NF-κB and HIF-1α as well as modulation of ROS. It can penetrate across the membrane, replenishes intracellular and glutathione and GSH to help the cell fight against oxidative stress. For these reasons, it has the potential for the treatment of neurodegeneration (such as Parkinson’s disease), radiation exposure and other disorders caused by oxidation. Moreover, it can also attenuate the allergic airway diseases.

化学的特性

Acetylcysteine also known as N-acetylcysteine or N-acetyl-Lcysteine (abbreviated NAC), is a pharma ceutical drug and nutritional supplement used primarily as a mucolytic agent and in the management of paracetamol (acetaminophen) overdose. Other uses include sulfate repletion in conditions, such as autism, where cysteine and related sulfur amino acids may be depleted.
Acetylcysteine is a derivative of cysteine; an acetyl group is attached to the nitrogen atom. This compound is sold as a dietary supplement commonly claiming antioxidant and liver protecting effects. It is used as a cough medicine because it breaks disulfide bonds in mucus and liquefies it, making it easier to cough up. It is also this action of breaking disulfide bonds that makes it useful in thinning the abnormally thick mucus in cystic and pulmonary fibrosis patients. In India it is marketed by Intas under the trade name 'Efetil'.

化学的特性

Acetylcysteine is the N-acetyl derivative of the amino acid Lcysteine, and is a precursor in the formation of the antioxidant glutathione in the body. The thiol (sulfhydryl) group confers antioxidant effects and is able to reduce free radicals.

化学的特性

White or almost white, crystalline powder or colourless crystals

使用

A metabolite of Methyl Isocyanate.

使用

Paracetamol overdose
Intravenous acetylcysteine is indicated for the treatment of paracetamol (acetaminophen) overdose. When paracetamol is taken in large quantities, a minor metabolite called N-acetyl-p-benzoquinone imine (NAPQI) accumulates within the body. It is normally conjugated by glutathione, but when taken in excess, the body's glutathione reserves are not sufficient to inactivate the toxic NAPQI. This metabolite is then free to react with key hepatic enzymes, therefore damaging hepatocytes. This may lead to severe liver damage and even death by fulminant liver failure.
For this indication, acetylcysteine acts to augment the glutathione reserves in the body and, together with glutathione, directly bind to toxic metabolites. These actions serve to protect hepatocytes in the liver from NAPQI toxicity.
Mucolytic therapy
?Inhaled acetylcysteine is indicated for mucolytic (""mucusdissolving"") therapy as an adjuvant in respiratory conditions with excessive and / or thick mucus production. Such conditions include emphysema, bronchitis, tuberculosis, bronchiectasis, amyloidosis, pneumonia, cystic fibrosis, chronic obstructive pulmonary disease, and pulmonary fibrosis. It is also used post-operatively, as a diagnostic aid, and in tracheotomy care. It may be considered ineffective in cystic fibrosis.For this indication, acetylcysteine acts to reduce mucus viscosity by splitting disulfide bonds linking proteins present in the mucus (mucoproteins).
Nephroprotective agent
Oral acetylcysteine is used for the prevention of radiocontrastinduced nephropathy (a form of acute renal failure). Some studies show that prior administration of acetylcysteine markedly decreases radiocontrast nephropathy, whereas others appear to cast doubt on its efficacy.
Treatment of cyclo phosphamide - induced hemorrhagic cystitis
Acetylcysteine has been used for cyclophosphamide-induced hemorrhagic cystitis, although mesna is generally preferred due to the ability of acetylcysteine to diminish the effectiveness of cyclophosphamide.
Microbiological use
Acetylcysteine can be used in Petroff's method i.e. liquefaction and decontamination of sputum, in preparation for diagnosis of tuberculosis.
Interstitial lung disease
Acetylcysteine is used in the treatment of interstitial lung disease to prevent disease progression.
Psychiatry
Acetylcysteine has been shown to reduce the symptoms of both schizophrenia and bipolar disorder in two placebo controlled trials conducted at Melbourne University. It is thought to act via modulation of NMDA glutamate receptors or by increasing glutathione.
Poly cystic ovary syndrome
In a small prospective trial comparing acetylcysteine to metformin (which is the standard drug treatment for PCOS), both treatments resulted in a significant decrease in body mass index, hirsutism score, fasting insulin, HOMA index, free testosterone and menstrual irregularity compared with baseline values, and both treatments had equal efficacy.

使用

An antioxidant mucolytic acetylated amino acid.

使用

n-acetyl-l-cysteine is a skin conditioner. It may also be used as an anti-aging ingredient given a demonstrated ability to regulate skin atrophy and reduce the appearance of fine lines and wrinkles.

定義

ChEBI: An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.

brand name

Acetadote (Cumberland); Mucomyst (Apothecon); Mucosil (Dey).

副作用

Researchers at the University of Virginia reported in 2007 study using very large doses in a mouse model that acetylcysteine could potentially cause damage to the heart and lungs. They found that acetyl cysteine was metabolized to S-nitroso-N-acetyl cysteine (SNOAC), which increased blood pressure in the lungs and right ventricle of the heart (pulmonary artery hypertension) in mice treated with acetylcysteine. The effect was similar to that observed following a 3-week exposure to an oxygen - deprived environment (chronic hypoxia). The authors also found that SNOAC induced a hypoxia-like response in the expression of several important genes both in vitro and in vivo.
The implications of these findings for long-term treatment with acetylcysteine have not yet been investigated. The dose used by Palmer and colleagues was dramatically higher than that used in humans; nonetheless, positive effects on age-diminished control of respiration (the hypoxic ventilatory response) have been observed previously in human subjects at more moderate doses.

安全性プロファイル

Poison by intraperitoneal route. Moderately toxic by other routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO, and SOx,

酵素阻害剤

These neuroprotective antoxidants and copper chelators (N-Acetyl-L- cycteine: FWfree-acid = 163.20 g/mol; CAS 616-91-1; Abbreviation: NAC; (N-Acetyl-L-cycteine amide: FWfree-acid = 162.21 g/mol; CAS 38520-57-9; Abbreviation: NACA) are metabolizable cysteine derivatives that are frequently used as an antidote in acetaminophen (Tylenol) and carbon monoxide (CO) poisoning. After oral administration of a 200–400 mg dose, NAC enters circulation, where it is rapidly oxidized to its homo-disulfide, reaching peak plasma concentrations of 0.35–40 mg/L in 1–2 hours. Its volume of distribution is 0.33–0.47 L/kg, with significant protein binding of 50%. Upon transporter-independent cellular uptake, N-acetyl-L-cysteine is deacetylated, giving rise to elevated intracellular cysteine concentrations and thereby enhancing glutathione production. While NAC inhibits neuronal cell apoptosis, it induces apoptosis in smooth muscle cells. NAC inhibits homocysteine-enhanced expression of an ox-LDL receptor. N- acetylcysteine amide crosses the blood-brain barrier, chelating Cu2+ (which is known to catalyze free radical formation) and preventing ROS-induced activation of JNK, p38 and MMP-9. Note: Mercapturic acids are S- substituted derivatives of NAC. Target (s) : N4- (b-N- acetylglucosaminyl) -L-asparaginase, Ki = 3.2 mM; cysteine dioxygenase; alkaline phosphatase; HIV replication; prolyl/cysteinyl-tRNA synthetase, Methanocaldococcus jannaschii; alliin lyase; and 5’-nucleotidase; serine O-acetyltransferase .

Complexing agent

Acetyl cysteine has been used to complex palladium, to help it dissolve in water. This helps to remove palladium from drugs or precursors synthesized by palladium-catalyzed coupling reactions.

Dosage forms

Acetylcysteine is available in different dosage forms for different indications :
Solution for inhalation (Assist,Mucomyst, Mucosil) – inhaled for mucolytic therapy or ingested for nephroprotective effect (to protect the kidneys)
IV injection (Assist,Parvolex, Acetadote) – treatment of paracetamol/acetaminophen overdose
Oral solution – various indications.
Effervescent Tablets (200 mg) - Reolin (Hochland Pharma Germany), Solmucol (600 mg)(IBSA, Switzerland), Cystaline (Thailand), Mucinac (Cipla India), Siran (MegaPharm, Israel / Temmler Pharma, Germany), Amuco200 (Camox Pharmaceuticals, South Africa), ACC200 (Hexal Pharma, South Africa).
Ocular solution - for mucolytic therapy
Sachet (600 mg) - Bilim Pharmaceuticals, trebon N (Uni-Pharma Greece)
CysNAC (900 mg) – NeuroScience Inc.
PharmaNAC Effervescent Tablets (900 mg) - Bioadvantex Pharma.
The IV injection and inhalation preparations are, in general, prescription only, whereas the oral solution and the effervescent tablets are available over the counter in many countries.

Research

The following uses have not been well-established or investigated :
Acetylcysteine has been successfully used to aid in the treatment of cannabis dependence in adolescents. Acetylcysteine has had anecdotal reports and some research suggesting efficacy in preventing nail biting.
Acetylcysteine is being tested in a double blind trial in Systemic Lupus Erythematosus. The objective is to correct mitochondrial dysfunction.
Acetylcysteine has been shown to reduce cravings associated with chronic cocaine use in a study conducted at the Medical University of South Carolina.
It may reduce the incidence of chronic obstructive pulmonary disease (COPD) exacerbations. In the treatment of AIDS, acetylcysteine has been shown to cause a "marked increase in immunological functions and plasma albumin concentrations".

参考文献

http://www.sigmaaldrich.com/catalog/product/sigma/a0737?lang=en&region=US
Grinberg, L, et al. "N-acetylcysteine amide, a novel cell-permeating thiol, restores cellular glutathione and protects human red blood cells from oxidative stress." Free Radical Biology & Medicine 38.1(2005):136-145.
Zhang, Xinsheng, et al. "N-Acetylcysteine Amide Protects Against Methamphetamine-Induced Oxidative Stress and Neurotoxicity in Immortalized Human Brain Endothelial Cells." Brain Research1275(2009):87-95.
Penugonda, S, et al. "Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12."Brain Research 1056.2(2005):132.
Lee, Kyung Sun, et al. "A novel thiol compound, N-acetylcysteine amide, attenuates allergic airway disease by regulating activation of NF-|[kappa]|B and hypoxia-inducible factor-1|[alpha]|." Experimental & Molecular Medicine 39.6(2007):756.

N-アセチル-L-システイン 上流と下流の製品情報

原材料

準備製品


N-アセチル-L-システイン 生産企業

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616-91-1(N-アセチル-L-システイン)キーワード:


  • 616-91-1
  • BETA-(2-NAPHTHYL)-L-ALANINE
  • H-ALA(2-NAPH)-OH
  • H-ALA(2-NAPHTHYL)-OH
  • H-2-NAL-OH
  • H-L-2-NAL-OH
  • H-NAL(2)-OH
  • H-NAL-OH
  • L-3-(2'-NAPHTHYL)-ALANINE
  • L-3-(2-NAPHTHYL)ALANINE
  • L-2-NAPHTHYLALANINE
  • L-ALPHA-ACETAMIDO-BETA-MERCAPTOPROPIONIC ACID
  • L-BETA-2-NAPHTHYL-L-ALANINE
  • (r)-mercapturicaci
  • Acetein
  • Airbron
  • Broncholysin
  • broncholysin[mucolytic]
  • Brunac
  • component of Naxid
  • Cysteine, N-acetyl-, L-
  • Fabrol
  • Fluatox
  • fluimicilinfantil
  • Fluimucetin
  • Fluimucil
  • Flumicil
  • Flumucetin
  • Fluprowit
  • Inspir
  • L-Acetylcysteine
  • N-アセチル-L-システイン
  • パルボレックス
  • ムコフィリン
  • (R)-3-メルカプト-2-(アセチルアミノ)プロピオン酸
  • フルイムシル
  • ナシステリン
  • ブロンコリシン
  • N-アセチル-L-Cys-OH
  • サテリット
  • アセチルシステイン
  • Nα-アセチルシステイン
  • レスパイル
  • ムコソルビン
  • N-アセチルシステイン
  • (R)-2-(アセチルアミノ)-3-メルカプトプロピオン酸
  • アセテイン
  • アイルブロン
  • (2R)-2-(アセチルアミノ)-3-メルカプトプロピオン酸
  • フルイムセチン
  • ムコリチクム-ラッペ
  • (R)-2-アセチルアミノ-3-メルカプトプロピオン酸
  • メルカプツル酸
  • ムコミスト
  • インスピル
  • N-アセチル-L(+)-システイン
  • N‐アセチル‐L(+)‐システイン
  • N - アセチル-L- システイン
  • N -アセチル-L-システイン
  • アセチルシステイン (JP17)
  • アミノ酸
  • アミノ酸 (N-保護)
  • 抗酸化剤
  • 生化学
  • Ac-アミノ酸
  • 代謝産物
  • 解毒薬
  • 去痰薬
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