Compounds > n-acetyl-s-(2-hydroxyethyl)cysteine
Page last updated: 2024-11-07

n-acetyl-s-(2-hydroxyethyl)cysteine

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Description

N-acetyl-S-(2-hydroxyethyl)cysteine, also known as NAC, is a derivative of the amino acid cysteine. It is a potent antioxidant that is used to treat a variety of conditions, including acetaminophen overdose, chronic obstructive pulmonary disease (COPD), and infertility. NAC is thought to work by increasing levels of glutathione, a key antioxidant in the body. NAC is also being studied for its potential to prevent and treat cancer. NAC is a prodrug that is rapidly converted to cysteine in the body. Cysteine is a precursor to glutathione, which is a powerful antioxidant that helps to protect cells from damage caused by free radicals. NAC is also thought to have anti-inflammatory effects. NAC is available over-the-counter and by prescription. However, it is important to talk to your doctor before taking NAC, as it can interact with other medications.'

N-acetyl-S-(2-hydroxyethyl)cysteine: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID108009
CHEBI ID34960
SCHEMBL ID15794762
MeSH IDM0097969

Synonyms (24)

Synonym
15060-26-1
s-(2-hydroxyethyl)-n-acetyl-l-cysteine
2-hydroxyethylmercapturic acid
l-cysteine, n-acetyl-s-(2-hydroxyethyl)-
(2r)-2-acetamido-3-(2-hydroxyethylsulfanyl)propanoic acid
cysteine, n-acetyl-s-(2-hydroxyethyl)-
n-acetyl-s-2-hydroxyethyl-l-cysteine
19179-72-7
alanine, n-acetyl-3-((2-hydroxyethyl)thio)-
n-acetyl-s-(2-hydroxyethyl)cysteine
s-(beta-hydroxyethyl)mercapturic acid
unii-5125c7a0ek
5125c7a0ek ,
n-acetyl-s-(2-hydroxyethyl)-l-cysteine
s-(2-hydroxyethyl)-n-acetylcysteine
s-(.beta.-hydroxyethyl)mercapturic acid
alanine, n-acetyl-3-((2-hydroxyethyl)thio)-, l-
CHEBI:34960
SCHEMBL15794762
n -acetyl-s-(2-hydroxyethyl)-l-cysteine
DTXSID00914077
n-acetyl-s- (2-hydroxyethyl)-l-cysteine
Q27116339
(r)-2-acetamido-3-((2-hydroxyethyl)thio)propanoic acid

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
", N-acetyl-S-(1-cyano-2-hydroxyethyl)-L-cysteine (CHEMA) and N-acetyl-S-(2-hydroxyethyl)-L-cysteine (HEMA), were isolated from the urine of rats dosed with four successive doses of oxiranecarbonitrile (glycidonitrile, GN), 5 mg/kg, a reactive metabolic intermediate of acrylonitrile (AN)."( N-acetyl-S-(1-cyano-2-hydroxyethyl)-L-cysteine, a new urinary metabolite of acrylonitrile and oxiranecarbonitrile.
Linhart, I; Novák, J; Smejkal, J, 1988)		0.27
" Urinary CEMA levels show a clear dose-response relationship with daily cigarette consumption and urinary cotinine."( A column-switching liquid chromatography-tandem mass spectrometry method for quantitation of 2-cyanoethylmercapturic acid and 2-hydroxyethylmercapturic acid in Chinese smokers.
Gao, N; Hou, H; Hu, Q; Tang, G; Xiong, W; Zhang, X, 2012)		0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acyl-amino acidA carboxamide resulting from the formal condensation of a carboxylic acid with the amino group of an amino acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (60.00)18.7374
1990's1 (10.00)18.2507
2000's0 (0.00)29.6817
2010's2 (20.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.65

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.65 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethylene chlorohydrin
Ethylene Chlorohydrin: Used as a solvent, in the manufacture of insecticides, and for treating sweet potatoes before planting. May cause nausea, vomiting, pains in head and chest, stupefaction. Irritates mucous membranes and causes kidney and liver degeneration.. chloroethanol : An organochlorine compound that is ethanol substituted by at least one chloro group.		1.9610chloroethanolxenobiotic metabolite
formic acid
formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.		2.110monocarboxylic acidantibacterial agent;
astringent;
metabolite;
protic solvent;
solvent
methylene bromide
methylene bromide: RN given refers to parent cpd. dibromomethane : A member of the class of bromomethanes that is methane substituted by two bromo groups. It is produced by marine algae.		1.9610bromohydrocarbon;
bromomethanes		algal metabolite;
marine metabolite
disulfiram
[no description available]		1.9610organic disulfide;
organosulfur acaricide		angiogenesis inhibitor;
antineoplastic agent;
apoptosis inducer;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
EC 3.1.1.1 (carboxylesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
ferroptosis inducer;
fungicide;
NF-kappaB inhibitor
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.110aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
ethylene oxide
Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.		2.6630gas molecular entity;
oxacycle;
saturated organic heteromonocyclic parent		allergen;
mouse metabolite;
mutagen
ethylene dibromide
Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.		2.3620bromoalkane;
bromohydrocarbon		algal metabolite;
carcinogenic agent;
fumigant;
marine metabolite;
mouse metabolite;
mutagen
acrylonitrile
[no description available]		2.4120aliphatic nitrile;
volatile organic compound		antifungal agent;
carcinogenic agent;
fungal metabolite;
mutagen;
polar aprotic solvent
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		4.79100acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
2-cyanoethylene oxide
2-cyanoethylene oxide: acrylonitrile metabolite; structure in first source		1.9710
thiodiacetic acid
thiodiacetic acid: vinyl chloride metabolite in urine of rats		1.9610dicarboxylic acid
icig 1163
ICIG 1163: RN given refers to parent cpd; structure in first source		1.9610
n-acetyl-s-(2-cyanoethyl)cysteine
N-acetyl-S-(2-cyanoethyl)cysteine: major urinary metabolite of acrylonitrile; structure in first source		7.4920N-acyl-L-amino acid
carbocysteine
Carbocysteine: A compound formed when iodoacetic acid reacts with sulfhydryl groups in proteins. It has been used as an anti-infective nasal spray with mucolytic and expectorant action.. S-carboxymethyl-L-cysteine : An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.		1.9610L-cysteine thioether;
non-proteinogenic L-alpha-amino acid		mucolytic
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.110