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N-아세틸-L(+)-시스틴

N-아세틸-L(+)-시스틴
N-아세틸-L(+)-시스틴 구조식 이미지
카스 번호:
616-91-1
한글명:
N-아세틸-L(+)-시스틴
동의어(한글):
아세틸시스테인;N-아세틸-L(+)-시스틴;N-아세틸-L(+)-시스틴(N-ACETYL-L(+)-CYSTEINE)
상품명:
N-Acetyl-L-cysteine
동의어(영문):
ACC;LNAL;LNAC;ACC1;ACACA;Brunac;Fabrol;Inspir;NAC-TB;Tixair
CBNumber:
CB2127503
분자식:
C5H9NO3S
포뮬러 무게:
163.19
MOL 파일:
616-91-1.mol

N-아세틸-L(+)-시스틴 속성

녹는점
106-108 °C(lit.)
알파
-35.1 ºC (c=2,H2O)
밀도
1.249 (estimate)
굴절률
24 ° (C=JPC Method)
저장 조건
2-8°C
용해도
H2O: 100 mg/mL with heating
물리적 상태
Solid
산도 계수 (pKa)
pK1: 9.52 (30°C)
색상
White
수용성
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
안정성
Stable. Incompatible with strong oxidizing agents.
InChIKey
PWKSKIMOESPYIA-BYPYZUCNSA-N
CAS 데이터베이스
616-91-1(CAS DataBase Reference)
NIST
Acetylcysteine(616-91-1)
EPA
L-Cysteine, N-acetyl-(616-91-1)

안전

위험 카페고리 넘버 36/37/38
안전지침서 22-24/25
WGK 독일 3
RTECS 번호 HA1660000
F 고인화성물질 10-23
TSCA Yes
HS 번호 29309016
유해 물질 데이터 616-91-1(Hazardous Substances Data)
독성 LD50 orally in rats: 5050 mg/kg (Goldenthal)

N-아세틸-L(+)-시스틴 MSDS


N-Acetyl-L-(+)-cysteine

N-아세틸-L(+)-시스틴 C화학적 특성, 용도, 생산

개요

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.

화학적 성질

White or almost white, crystalline powder or colourless crystals

화학적 성질

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'.

화학적 성질

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.

용도

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.

용도

A metabolite of Methyl Isocyanate.

용도

An antioxidant mucolytic acetylated amino acid.

용도

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.

정의

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

상표명

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

부작용

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.

Safety Profile

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,

효소 저해제

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".

참고 문헌

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.

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