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Acetylcysteine

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		By mouth, intravenous, inhalation
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability6-10% (Oral)[6][7]
nearly 100% (intravenous)[8]
Protein binding50 to 83%[9]
MetabolismLiver[9]
Elimination half-life5.6 hours[5]
ExcretionKidney (30%),[9] faecal (3%)
Identifiers
  • (2R)-2-acetamido-3-sulfanylpropanoic acid[10]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.545 Edit this at Wikidata
Chemical and physical data
FormulaC5H9NO3S
Molar mass163.19 g·mol−1
3D model (JSmol)
Specific rotation+5° (c = 3% in water)[11]
Melting point109 to 110 °C (228 to 230 °F) [11]
  • C/C(=N/[C@@H](CS)C(=O)O)/O
  • 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 checkY
  • Key:PWKSKIMOESPYIA-BYPYZUCNSA-N checkY
  (verify)

Acetylcysteine, also known as N-acetylcysteine (NAC), not to be confused with N-acetylcarnosine, which is also abbreviated "NAC," is a medication that is used to treat paracetamol overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders like pneumonia and bronchitis.[9] It has been used to treat lactobezoar in infants. It can be taken intravenously, by mouth, or inhaled as a mist.[9] Some people use it as a dietary supplement.[12][13]

Common side effects include nausea and vomiting when taken by mouth.[9] The skin may occasionally become red and itchy with any route of administration.[9] A non-immune type of anaphylaxis may also occur.[9] It appears to be safe in pregnancy.[9] For paracetamol overdose, it works by increasing the level of glutathione, an antioxidant that can neutralise the toxic breakdown products of paracetamol.[9] When inhaled, it acts as a mucolytic by decreasing the thickness of mucus.[14]

Acetylcysteine was initially patented in 1960 and came into medical use in 1968.[15][16][17] It is on the World Health Organization's List of Essential Medicines.[18][19] It is available as a generic medication.[20]

The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids.[21][22]

  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. ^ "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.
  5. ^ a b "Acetadote- acetylcysteine injection, solution". DailyMed. 1 October 2021. Archived from the original on 30 December 2022. Retrieved 29 December 2022.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ "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.
  11. ^ a b Cite error: The named reference sial was invoked but never defined (see the help page).
  12. ^ Talbott SM (2012). A Guide to Understanding Dietary Supplements. Routledge. p. 469. ISBN 9781136805707. Archived from the original on 8 September 2017.
  13. ^ "Cysteine". University of Maryland Medical Center. Archived from the original on 1 July 2017. Retrieved 23 June 2017.
  14. ^ 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.
  15. ^ Fischer J, Ganellin CR (2006). Analogue-Based Drug Discovery. Weinheim: Wiley-VCH. p. 544. ISBN 9783527607495. Archived from the original on 8 September 2017.
  16. ^ 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
  17. ^ 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
  18. ^ Organization WH (2019). World Health Organization Model List of Essential Medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  19. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  20. ^ 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.
  21. ^ 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.
  22. ^ 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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