CHEBI:28939 - N-acetyl-L-cysteine

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ChEBI Name N-acetyl-L-cysteine
ChEBI ID CHEBI:28939
ChEBI ASCII Name N-acetyl-L-cysteine
Definition An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45481, CHEBI:2418, CHEBI:21548
Supplier Information ChemicalBook:CB2127503, eMolecules:29913760, eMolecules:474683, Selleckchem:Acetylcysteine, ZINC000003589203
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N-acetylcysteine, also known as Acetylcysteine and NAC, is a medication that is used to treat paracetamol (acetaminophen) overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders, such as pneumonia and bronchitis. It has been used to treat lactobezoar in infants. It can be taken intravenously, orally (swallowed by mouth), or inhaled as a mist. It is also sometimes used as a dietary supplement. Common side effects include nausea and vomiting when taken orally. The skin may occasionally become red and itchy with any route of administration. A non-immune type of anaphylaxis may also occur. It appears to be safe in pregnancy. For paracetamol overdose, it works by increasing the level of glutathione, an antioxidant that can neutralize the toxic breakdown products of paracetamol. When inhaled, it acts as a mucolytic by decreasing the thickness of mucus. Acetylcysteine was initially patented in 1960 and came into medical use in 1968. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids.
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Formula C5H9NO3S
Net Charge 0
Average Mass 163.19590
Monoisotopic Mass 163.03031
InChI InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
InChIKey PWKSKIMOESPYIA-BYPYZUCNSA-N
SMILES CC(=O)N[C@@H](CS)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) See: MetaboLights Study
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
ferroptosis inhibitor
Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antidote to paracetamol poisoning
A role borne by a molecule that acts to counteract or neutralize the deleterious effects of paracetamol (acetaminophen).
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
mucolytic
A compound that alters the structure of mucus so as to decrease its viscosity and thereby facilitate its removal by ciliary action and expectoration. Compare with antitussives, which suppress the cough reflex, and expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing.
vulnerary
A drug used in treating and healing of wounds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-acetyl-L-cysteine (CHEBI:28939) has role antidote to paracetamol poisoning (CHEBI:74529)
N-acetyl-L-cysteine (CHEBI:28939) has role antiinfective agent (CHEBI:35441)
N-acetyl-L-cysteine (CHEBI:28939) has role antioxidant (CHEBI:22586)
N-acetyl-L-cysteine (CHEBI:28939) has role antiviral drug (CHEBI:36044)
N-acetyl-L-cysteine (CHEBI:28939) has role ferroptosis inhibitor (CHEBI:173084)
N-acetyl-L-cysteine (CHEBI:28939) has role geroprotector (CHEBI:176497)
N-acetyl-L-cysteine (CHEBI:28939) has role human metabolite (CHEBI:77746)
N-acetyl-L-cysteine (CHEBI:28939) has role mucolytic (CHEBI:77034)
N-acetyl-L-cysteine (CHEBI:28939) has role radical scavenger (CHEBI:48578)
N-acetyl-L-cysteine (CHEBI:28939) has role vulnerary (CHEBI:73336)
N-acetyl-L-cysteine (CHEBI:28939) is a N-acetyl-L-amino acid (CHEBI:21545)
N-acetyl-L-cysteine (CHEBI:28939) is a L-cysteine derivative (CHEBI:83824)
N-acetyl-L-cysteine (CHEBI:28939) is a acetylcysteine (CHEBI:22198)
N-acetyl-L-cysteine (CHEBI:28939) is conjugate acid of N-acetyl-L-cysteinate (CHEBI:78236)
Incoming S-substituted N-acetyl-L-cysteine (CHEBI:47911) has functional parent N-acetyl-L-cysteine (CHEBI:28939)
N-acetyl-L-cysteinate (CHEBI:78236) is conjugate base of N-acetyl-L-cysteine (CHEBI:28939)
N-acetyl-L-cysteinyl residue (CHEBI:133372) is substituent group from N-acetyl-L-cysteine (CHEBI:28939)
IUPAC Name
N-acetyl-L-cysteine
INNs Sources
acetilcisteina ChemIDplus
acetylcysteinum ChemIDplus
Synonyms Sources
(2R)-2-acetylamino-3-sulfanylpropanoic acid IUPAC
(R)-2-acetylamino-3-mercaptopropanoic acid ChEBI
(R)-mercapturic acid ChemIDplus
Acetylcysteine KEGG COMPOUND
L-acetylcysteine ChemIDplus
L-α-acetamido-β-mercaptopropionic acid NIST Chemistry WebBook
mercapturic acid ChemIDplus
N-acetyl-L-(+)-cysteine NIST Chemistry WebBook
N-ACETYL-L-CYSTEINE PDBeChem
N-acetylcysteine ChemIDplus
NAC ChEBI
Manual Xrefs Databases
66 DrugCentral
Acetylcysteine Wikipedia
C06809 KEGG COMPOUND
CPD-9175 MetaCyc
D00221 KEGG DRUG
DB06151 DrugBank
HMDB0001890 HMDB
LSM-4672 LINCS
SC2 PDBeChem
View more database links
Registry Numbers Types Sources
142554 Gmelin Registry Number Gmelin
1724426 Reaxys Registry Number Reaxys
616-91-1 CAS Registry Number KEGG COMPOUND
616-91-1 CAS Registry Number NIST Chemistry WebBook
616-91-1 CAS Registry Number ChemIDplus
Citations
Hou Y, Wang L, Yi D, Wu G (2015)
N-acetylcysteine and intestinal health: a focus on its mechanism of action.
Frontiers in bioscience (Landmark edition) 20, 872-891 [PubMed:25553484]
[show Abstract]
Allaveisi F, Hashemi B, Mortazavi SM (2014)
Effect of gamma sterilization on microhardness of the cortical bone tissue of bovine femur in presence of N-Acetyl-L-Cysteine free radical scavenger.
Physica medica : PM : an international journal devoted to the applications of physics to medicine and biology : official journal of the Italian Association of Biomedical Physics (AIFB) 30, 314-319 [PubMed:24119926]
[show Abstract]
Flurkey K, Astle CM, Harrison DE (2010)
Life extension by diet restriction and N-acetyl-L-cysteine in genetically heterogeneous mice.
The journals of gerontology. Series A, Biological sciences and medical sciences 65, 1275-1284 [PubMed:20819793]
[show Abstract]
Shibamura A, Ikeda T, Nishikawa Y (2009)
A method for oral administration of hydrophilic substances to Caenorhabditis elegans: Effects of oral supplementation with antioxidants on the nematode lifespan.
Mechanisms of ageing and development 130, 652-655 [PubMed:19580823]
[show Abstract]
Nagata M, Arimitsu N, Ito T, Sekimizu K (2007)
Antioxidant N-acetyl-L-cysteine inhibits erythropoietin-induced differentiation of erythroid progenitors derived from mouse fetal liver.
Cell biology international 31, 252-256 [PubMed:17174578]
[show Abstract]
Lucena MI, López-Torres E, Verge C, Andrade RJ, Puche MJ, Seoane J, de la Cuesta FS (2005)
The administration of N-acetylcysteine causes a decrease in prothrombin time in patients with paracetamol overdose but without evidence of liver impairment.
European journal of gastroenterology & hepatology 17, 59-63 [PubMed:15647642]
[show Abstract]
Hein OV, Ohring R, Schilling A, Oellerich M, Armstrong VW, Kox WJ, Spies C (2004)
N-acetylcysteine decreases lactate signal intensities in liver tissue and improves liver function in septic shock patients, as shown by magnetic resonance spectroscopy: extended case report.
Critical care (London, England) 8, R66-71 [PubMed:15025780]
[show Abstract]
Fulghesu AM, Ciampelli M, Muzj G, Belosi C, Selvaggi L, Ayala GF, Lanzone A (2002)
N-acetyl-cysteine treatment improves insulin sensitivity in women with polycystic ovary syndrome.
Fertility and sterility 77, 1128-1135 [PubMed:12057717]
[show Abstract]
Weigand MA, Plachky J, Thies JC, Spies-Martin D, Otto G, Martin E, Bardenheuer HJ (2001)
N-acetylcysteine attenuates the increase in alpha-glutathione S-transferase and circulating ICAM-1 and VCAM-1 after reperfusion in humans undergoing liver transplantation.
Transplantation 72, 694-698 [PubMed:11544433]
[show Abstract]
Baldwin RW, Clegg JA, Curran AC, Austin EB, Khan T, Ma Y, Gunn B, Hudecz F, Byers VS, Lepoittevin JP, Price MR (1999)
Regulation of the contact sensitivity response to urushiol with anti-urushiol monoclonal antibody ALG 991.
Archives of dermatological research 291, 652-658 [PubMed:10651166]
[show Abstract]
Bailey B, McGuigan MA (1998)
Management of anaphylactoid reactions to intravenous N-acetylcysteine.
Annals of emergency medicine 31, 710-715 [PubMed:9624310]
[show Abstract]
Jones AL (1998)
Mechanism of action and value of N-acetylcysteine in the treatment of early and late acetaminophen poisoning: a critical review.
Journal of toxicology. Clinical toxicology 36, 277-285 [PubMed:9711192]
[show Abstract]
Longo A, Di Toro M, Galimberti C, Carenzi A (1991)
Determination of N-acetylcysteine in human plasma by gas chromatography-mass spectrometry.
Journal of chromatography 562, 639-645 [PubMed:2026726]
[show Abstract]
Last Modified
28 October 2021