Acetylcysteine

Not to be confused with N-Acetylcarnosine, for the proposed treatment of cataracts.

Acetylcysteine
Clinical data
Pronunciation/əˌsiːtəlˈsɪstiːn/ and similar (/əˌsɛtəl-, ˌæsɪtəl-, -tiːn/)
Trade namesACC 200, Acetadote, Fluimucil, Mucomyst, others
Other namesN-acetylcysteine; N-acetyl-L-cysteine; NALC; NAC
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B2
Routes of
administration		oral, intravenous, inhalation
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability6–10% (Oral)[7][8]
nearly 100% (intravenous)[9]
Protein binding50 to 83%[10]
MetabolismLiver[10]
Elimination half-life5.6 hours[6]
ExcretionKidney (30%),[10] faecal (3%)
Identifiers
IUPAC name
  • (2R)-2-acetamido-3-sulfanylpropanoic acid[11]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.545
Chemical and physical data
FormulaC5H9NO3S
Molar mass163.19 g·mol−1
3D model (JSmol)
Specific rotation+5° (c = 3% in water)[12]
Melting point109 to 110 °C (228 to 230 °F) [12]
SMILES
  • C/C(=N/[C@@H](CS)C(=O)O)/O
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 Y
  • Key:PWKSKIMOESPYIA-BYPYZUCNSA-N Y
  (verify)

N-acetylcysteine or Acetylcysteine (NAC) (not to be confused with N-Acetylcarnosine, which is also abbreviated "NAC") is a mucolytic that is used to treat paracetamol (acetaminophen) overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders, such as pneumonia and bronchitis.[10][13] It has been used to treat lactobezoar in infants. It can be taken intravenously, orally (swallowed by mouth), or inhaled as a mist by use of a nebulizer.[10][14] It is also sometimes used as a dietary supplement.[15][16]

Common side effects include nausea and vomiting when taken orally.[10] The skin may occasionally become red and itchy with any route of administration.[10] A non-immune type of anaphylaxis may also occur.[10] It appears to be safe in pregnancy.[10] For paracetamol overdose, it works by increasing the level of glutathione, an antioxidant that can neutralize the toxic breakdown products of paracetamol.[10] When inhaled, it acts as a mucolytic by decreasing the thickness of mucus.[17]

Acetylcysteine was initially patented in 1960 and came into medical use in 1968.[18][19][20] It is on the World Health Organization's List of Essential Medicines.[21] It is available as a generic medication.[22]

The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids.[23][24]

  1. ^ DBL ACETYLCYSTEINE injection concentrate acetylcysteine 2 g/ 10 mL injection ampoule
  2. ^ "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 30 December 2022. Retrieved 30 December 2022.
  3. ^ "Acetylcysteine (Omegapharm)". Healthdirect Australia. 30 November 2022. Archived from the original on 30 December 2022. Retrieved 29 December 2022.
  4. ^ "Therapeutic Goods (Poisons Standard—February 2025) Instrument 2025". Federal Register of Legislation. February 2025. Retrieved 5 April 2025.
  5. ^ "Acepiro 600 mg effervescent tablets - Summary of Product Characteristics (SmPC)". (emc). 30 August 2022. Archived from the original on 30 December 2022. Retrieved 29 December 2022.
  6. ^ a b "Acetadote- acetylcysteine injection, solution". DailyMed. 1 October 2021. Archived from the original on 30 December 2022. Retrieved 29 December 2022.
  7. ^ Tsikas D, Mikuteit M (September 2022). "N-acetyl-L-cysteine in human rheumatoid arthritis and its effects on nitric oxide (NO) and malondialdehyde (MDA): analytical and clinical considerations". Amino Acids. 54 (9): 1251–1260. doi:10.1007/s00726-022-03185-x. PMC 9372125. PMID 35829920.
  8. ^ Stockley RA (2008). Chronic Obstructive Pulmonary Disease a Practical Guide to Management. Chichester: John Wiley & Sons. p. 750. ISBN 9780470755280. Archived from the original on 8 September 2017.
  9. ^ Luo A, Liu X, Hu Q, Yang M, Jiang H, Liu W (March 2022). "Efficacy of N-acetylcysteine on idiopathic or postinfective non-cystic fibrosis bronchiectasis: a systematic review and meta-analysis protocol". BMJ Open. 12 (3): e053625. doi:10.1136/bmjopen-2021-053625. PMC 8971804. PMID 35361640. Archived from the original on 6 August 2024. Retrieved 5 August 2024.
  10. ^ a b c d e f g h i j "Acetylcysteine". The American Society of Health-System Pharmacists. Archived from the original on 23 September 2015. Retrieved 22 August 2015.
  11. ^ "L-Cysteine, N-acetyl- — Compound Summary". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. 25 March 2005. Identification. Archived from the original on 12 January 2014. Retrieved 9 January 2012.
  12. ^ a b Cite error: The named reference Sigma-2014 was invoked but never defined (see the help page).
  13. ^ "ACC® 600 ORAL POWDER" (PDF). Sandoz. Archived from the original on 12 June 2025. Retrieved 12 June 2025. Acetylcysteine is a mucolytic agent that reduces the viscosity of non-infected bronchial secretions probably by the splitting of disulphide bonds in mucoproteins.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
  14. ^ "Acetylcysteine Oral Inhalation: MedlinePlus Drug Information". MedlinePlus. Retrieved 22 February 2025. Acetylcysteine comes as a solution (liquid) and concentrated solution to inhale by mouth using a nebulizer ...
  15. ^ Talbott SM (2012). A Guide to Understanding Dietary Supplements. Routledge. p. 469. ISBN 9781136805707. Archived from the original on 8 September 2017.
  16. ^ "Cysteine". University of Maryland Medical Center. Archived from the original on 1 July 2017. Retrieved 23 June 2017.
  17. ^ Sadowska AM, Verbraecken J, Darquennes K, De Backer WA (December 2006). "Role of N-acetylcysteine in the management of COPD". International Journal of Chronic Obstructive Pulmonary Disease. 1 (4): 425–434. doi:10.2147/copd.2006.1.4.425. PMC 2707813. PMID 18044098.
  18. ^ Fischer J, Ganellin CR (2006). Analogue-Based Drug Discovery. Weinheim: Wiley-VCH. p. 544. ISBN 9783527607495. Archived from the original on 8 September 2017.
  19. ^ US3091569A, Sheffner AL, "Mucolytic-nu-acylated sulfhydryl compositions and process for treating animal mucus", issued 28 May 1963  Archived 6 August 2024 at the Wayback Machine
  20. ^ US patent 3091569, Sheffner AL, "Mucolytic-N-acylated sulfhydryl compositions and process for treating animal mucus", published 28 May 1963, issued 28 May 1963, assigned to Mead Johnson & Co  Archived 30 June 2024 at the Wayback Machine
  21. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  22. ^ Baker E (2014). "Acetylcysteine". Top 100 Drugs: Clinical pharmacology and practical prescribing. Elsevier Health Sciences. ISBN 9780702055157. Archived from the original on 8 September 2017.
  23. ^ Bin P, Huang R, Zhou X (2017). "Oxidation Resistance of the Sulfur Amino Acids: Methionine and Cysteine". BioMed Research International. 2017: 9584932. doi:10.1155/2017/9584932. PMC 5763110. PMID 29445748.
  24. ^ Lee BC, Dikiy A, Kim HY, Gladyshev VN (November 2009). "Functions and evolution of selenoprotein methionine sulfoxide reductases". Biochimica et Biophysica Acta (BBA) - General Subjects. 1790 (11): 1471–1477. doi:10.1016/j.bbagen.2009.04.014. PMC 3062201. PMID 19406207.
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