Acetylcysteine

Base Information

• Chemical Name: Acetylcysteine
• CAS No.: 616-91-1
• Deprecated CAS: 7696-05-1,1261105-20-7,1261105-20-7
• Molecular Formula: C5H9NO3S
• Molecular Weight: 163.197
• Hs Code.: 29309016
• European Community (EC) Number: 210-498-3
• UNII: WYQ7N0BPYC
• DSSTox Substance ID: DTXSID5020021
• Nikkaji Number: J3.309J
• Wikipedia: Acetylcysteine
• Wikidata: Q375613
• NCI Thesaurus Code: C200
• RXCUI: 197
• Metabolomics Workbench ID: 37912
• ChEMBL ID: CHEMBL600
• Mol file: 616-91-1.mol

Synonyms:Acétylcystéine GNR;acebraus;Acemuc;Acetabs;Acetylcystein AL;Acetylcystein Atid;Acetylcystein Heumann;Acetylcystein Trom;Acetylcystein, mentopin;Acetylcysteine;Acetylcysteine Hydrochloride;Acetylcysteine Sodium;Acetylcysteine Zinc;Acetylcysteine, (D)-Isomer;Acetylcysteine, (DL)-Isomer;Acetylcysteine, Monoammonium Salt;Acetylcysteine, Monosodium Salt;Acetylin;Acetyst;Acid, Mercapturic;Airbron;Alveolex;Azubronchin;Bisolvon NAC;Bromuc;Broncho Fips;Broncho-Fips;BronchoFips;Broncholysin;Broncoclar;Codotussyl;Cystamucil;Dampo Mucopect;durabronchal;Eurespiran;Exomuc;Fabrol;Fluimucil;Fluprowit;Frekatuss;Genac;Hoestil;Hustengetr?nk, Optipect;Hydrochloride, Acetylcysteine;Ilube;Jenacystein;Jenapharm;Lantamed;Larylin NAC;Lindocetyl;M Pectil;M-Pectil;mentopin Acetylcystein;Mercapturic Acid;Monoammonium Salt Acetylcysteine;Monosodium Salt Acetylcysteine;MPectil;Muciteran;Muco Sanigen;Mucomyst;Mucopect, Dampo;Mucosil;Mucosol;Mucosolvin;N Acetyl L cysteine;N Acetylcysteine;N-Acetyl-L-cysteine;N-Acetylcysteine;NAC AL;NAC Zambon;NAC, Bisolvon;Optipect Hustengetr?nk;Sanigen, Muco;Siccoral;Siran;Sodium, Acetylcysteine;Solmucol;Zambon, NAC;Zinc, Acetylcysteine

Chemical Property of Acetylcysteine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 8.68E-08mmHg at 25°C
• Melting Point: 106-108 °C
• Refractive Index: 24 ° (C=JPC Method)
• Boiling Point: 407.678 °C at 760 mmHg
• PKA: pK1: 9.52 (30°C)
• Flash Point: 200.357 °C
• PSA: 105.20000
• Density: 1.295 g/cm³
• LogP: -0.10360
• Storage Temp.: 2-8°C
• Solubility.: H2O: 100 mg/mL with heating
• Water Solubility.: Soluble in water, ethanol, methanol, dimethyl sulfoxide, hot isopropyl alcohol, methyl acetate and ethyl acetate. Insoluble in c
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 163.03031432
• Heavy Atom Count: 10
• Complexity: 148

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antidotes, Toxicological Emergency
• Canonical SMILES: CC(=O)NC(CS)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CS)C(=O)O
• Recent ClinicalTrials: Amiodarone and N-Acetylcysteine or Amiodarone Alone for Preventing Atrial Fibrillation After Thoracic Surgery
• Recent EU Clinical Trials: Efficacy and safety of the combination of acetylcysteine, paracetamol and phenylephrine for the treatment of common cold: a prospective, randomized, double-blind, controlled trial
• Description: N-Acetyl-L-cysteine 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.
• Uses: Paracetamol overdoseIntravenous N-Acetyl-L-cysteine?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, N-Acetyl-L-cysteine?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 therapyInhaled N-Acetyl-L-cysteine?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, N-Acetyl-L-cysteine?acts to reduce mucus viscosity by splitting disulfide bonds linking proteins present in the mucus (mucoproteins).Nephroprotective agentOral N-Acetyl-L-cysteine?is used for the prevention of radiocontrastinduced nephropathy (a form of acute renal failure). Some studies show that prior administration of N-Acetyl-L-cysteine?markedly decreases radiocontrast nephropathy, whereas others appear to cast doubt on its efficacy.Treatment of cyclo phosphamide - induced hemorrhagic cystitisN-Acetyl-L-cysteine?has been used for cyclophosphamide-induced hemorrhagic cystitis, although mesna is generally preferred due to the ability of N-Acetyl-L-cysteine?to diminish the effectiveness of cyclophosphamide.Microbiological useN-Acetyl-L-cysteine?can be used in Petroff's method i.e. liquefaction and decontamination of sputum, in preparation for diagnosis of tuberculosis.Interstitial lung diseaseN-Acetyl-L-cysteine?is used in the treatment of interstitial lung disease to prevent disease progression.PsychiatryN-Acetyl-L-cysteine?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 syndromeIn a small prospective trial comparing N-Acetyl-L-cysteine?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. A metabolite of Methyl Isocyanate.N-Acetyl-L-cysteine, by itself a poor scavenger of oxidants, is converted inside cells to yield sulfane sulfur species, which are very potent scavengers of oxidants. 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. 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.
• Clinical Use: Treatment of paracetamol overdose Renal protection during radiological scans involving contrast media (unlicensed) Treatment of mucolytic in respiratory disorders
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Acetylcysteine

There total 23 articles about Acetylcysteine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

acetic anhydride (108-24-7) + L-cysteine hydrochloride monohydrate (7048-04-6,116797-51-4) → N-acetylcystein (616-91-1,7696-05-1)

Guidance literature:

With sodium acetate; In tetrahydrofuran; water; at 10 - 60 ℃; for 37h; pH=4 - 5; Inert atmosphere;

Reference yield:

2-Acetylamino-3-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-propionic acid → N-Acetylcysteine (7218-04-4,26117-28-2,616-91-1,7696-05-1)

Guidance literature:

With lithium perchlorate; In methanol; (electrolysis);

DOI:10.1021/ja00769a087

Reference yield:

N-acetyl-S-benzyl-D,L-cysteine (19538-71-7) → N-Acetylcysteine (7218-04-4,26117-28-2,616-91-1,7696-05-1)

Guidance literature:

With ammonia; sodium;

DOI:10.1021/jm00309a057

upstream raw materials:

Ketene

L-cystine

acetic anhydride

Isopropenyl acetate

Downstream raw materials:

(R)-2-acetamido-3-(phenylthio)propanoic acid

S-(2,4-dinitrophenyl)-N-acetyl-L-cysteine

S-n-Propyl-N-acetyl-L-cysteine

N-acetyl-S-(2-thienyl)-L-cysteine

Refernces

• 1、 -. "Separation and purification method for acetylcysteine enantiomer". Paragraph 0062-0128. . Retrieved 2020/01/12.
• 2、 -. "Peptide Tyrosinase Activators". . . Retrieved 2015/06/10.