N-Ацетил-L-цистеин

Описание

N-Acetyl-L-cysteine is an N-acetylated derivative of cysteine, which contains a sulfhydryl group in the molecule, which can break the disulfide bond (-S-S-) of the mucin peptide bond, so that the mucin chain becomes a small molecule peptide chain, reducing The viscosity of mucin, so It is a dissolving drug for mucus in mucus, purulent sputum and respiratory tract.

Химические свойства

N-Acetyl-L-cysteine is a white crystalline powder that has a garlic-like smell and sour taste. It is hygroscopic, and can dissolve in water or ethanol, but is insoluble in ether and chloroform. This substance is also acidic in aqueous solution, with a pH range of 2-2.75 for a concentration of 10g/L H2O.

Использование

An antioxidant mucolytic acetylated amino acid.
N-acetyl-l-cysteine (NAC) is a derivative of the dietary amino acid l-cysteine. NAC has a high affinity for lung tissue, which it supports through mucolytic and antioxidant action. NAC also enhances glutathione production and plays a role in heavy metal detoxification.

Определение

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

преимущество

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.

Общее описание

N-Acetyl-L-cysteine 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. 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'.

Механизм действия

N-Acetyl-L-cysteine is a kind of membrane penetrating antioxidant. It has anti-inflammatory activity through regulating the activation of NF-KB 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. In addition to its antioxidant action, NAC acts as a vasodilator by facilitating the production and action of nitric oxide. This property is an important mechanism of action in the prophylaxis of contrast-induced nephropathy and the potentiation of nitrate-induced vasodilation (Millea 2009).

Побочные эффекты

At dosages of 1,200 mg twice daily or lower, N-acetylcysteine is well tolerated. At these dosages, side effects are unusual, but may include nausea, vomiting, diarrhea, transient skin rash, flushing, epigastric pain, and constipation.
www.aafp.org

Профиль безопасности

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,

Ветеринарные препараты и методы лечения

N-Acetyl-L-cysteine is a mucolytic agent that can be used to stop the melting effect of collagenases and proteases on the cornea. It is useful in halting melting through inhibition of metalloproteinases, but is not felt to be useful for melting caused by infectious agents.

Химические свойства

N-ацетил-L-цистеин белый кристаллический порошок с запахом, похожим на чеснок, кислым вкусом. Обладает гигроскопичностью, легко растворим в воде или этаноле, но нерастворим в эфире и хлороформе.

Применение

N-ацетил-L-цистеин может быть использован в качестве растворителя мокроты и применяется при обструкции дыхания, вызванной большим количеством затвердевшей мокроты. Кроме того, его можно использовать в качестве антидота при отравлении парацетамолом.

Безопасность

Поскольку N-ацетил-L-цистеин имеет специфический запах, его употребление может вызвать тошноту. Он имеет раздражающее действие на дыхательные пути, может вызвать спазм бронхов, обычно используется в комбинации с бронходилататорами, такими как изопреналин, а также с ингалятором для мокроты. Не следует контактировать с металлами (например, Fe, Cu), резиной, окислителями и т.д. Нельзя использовать одновременно с антибиотиками, такими как пенициллин, цефалоспорины, тетрациклины и т.п., чтобы не снижать их антибактериальное действие. С осторожностью применяется у пациентов с бронхиальной астмой.

Производство

Используя L-цистеин и ацетоангидрид в качестве исходных материалов, проводят реакцию ацилирования, получают сырой продукт, который подчищают активированным углем и эфиром, получают готовый продукт N-ацетил-L-цистеин.

использованная литература

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.