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Acetylcysteine information


Acetylcysteine
Clinical data
Pronunciation/əˌstəlˈsɪstn/ and similar (/əˌsɛtəl-, ˌæsɪtəl-, -tn/)
Trade namesACC 200, Acetadote, Fluimucil, Mucomyst, others
Other namesN-acetylcysteine; N-acetyl-L-cysteine; NALC; NAC
AHFS/Drugs.comMonograph
License data
  • US DailyMed: Acetylcysteine
Pregnancy
category
  • AU: B2
Routes of
administration
By mouth, intravenous, inhalation
ATC code
  • R05CB01 (WHO) S01XA08 (WHO) V03AB23 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[1][2][3]
  • UK: POM (Prescription only)[4]
  • US: ℞-only[5]
Pharmacokinetic data
Bioavailability10% (Oral)[6]
Protein binding50 to 83%[7]
MetabolismLiver[7]
Elimination half-life5.6 hours[5]
ExcretionKidney (30%),[7] faecal (3%)
Identifiers
IUPAC name
  • (2R)-2-acetamido-3-sulfanylpropanoic acid[8]
CAS Number
  • 616-91-1 checkY
PubChem CID
  • 12035
DrugBank
  • DB06151 checkY
ChemSpider
  • 11540 checkY
UNII
  • WYQ7N0BPYC
KEGG
  • D00221 checkY
ChEBI
  • CHEBI:28939 checkY
ChEMBL
  • ChEMBL600 checkY
CompTox Dashboard (EPA)
  • DTXSID5020021 Edit this at Wikidata
ECHA InfoCard100.009.545 Edit this at Wikidata
Chemical and physical data
FormulaC5H9NO3S
Molar mass163.19 g·mol−1
3D model (JSmol)
  • Interactive image
Specific rotation+5° (c = 3% in water)[9]
Melting point109 to 110 °C (228 to 230 °F) [9]
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 checkY
  • Key:PWKSKIMOESPYIA-BYPYZUCNSA-N checkY
  (verify)

Acetylcysteine, also known as N-acetylcysteine (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.[7] It has been used to treat lactobezoar in infants. It can be taken intravenously, by mouth, or inhaled as a mist.[7] Some people use it as a dietary supplement.[10][11]

Common side effects include nausea and vomiting when taken by mouth.[7] The skin may occasionally become red and itchy with any route of administration.[7] A non-immune type of anaphylaxis may also occur.[7] It appears to be safe in pregnancy.[7] For paracetamol overdose, it works by increasing the level of glutathione, an antioxidant that can neutralise the toxic breakdown products of paracetamol.[7] When inhaled, it acts as a mucolytic by decreasing the thickness of mucus.[12]

Acetylcysteine was initially patented in 1960 and came into medical use in 1968.[13][14][15] It is on the World Health Organization's List of Essential Medicines.[16][17] It is available as a generic medication.[18]

The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids.[19][20]

  1. ^ DBL ACETYLCYSTEINE injection concentrate acetylcysteine 2 g/ 10 mL injection ampoule
  2. ^ "TGA eBS - Product and Consumer Medicine Information Licence".
  3. ^ "Acetylcysteine (Omegapharm)". Healthdirect Australia. 30 November 2022. Retrieved 29 December 2022.
  4. ^ "Acepiro 600 mg effervescent tablets - Summary of Product Characteristics (SmPC)". (emc). 30 August 2022. Retrieved 29 December 2022.
  5. ^ a b "Acetadote- acetylcysteine injection, solution". DailyMed. 1 October 2021. Retrieved 29 December 2022.
  6. ^ 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.
  7. ^ 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.
  8. ^ "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.
  9. ^ a b Cite error: The named reference sial was invoked but never defined (see the help page).
  10. ^ Talbott SM (2012). A Guide to Understanding Dietary Supplements. Routledge. p. 469. ISBN 9781136805707. Archived from the original on 8 September 2017.
  11. ^ "Cysteine". University of Maryland Medical Center. Archived from the original on 1 July 2017. Retrieved 23 June 2017.
  12. ^ 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. ISSN 1176-9106. PMC 2707813. PMID 18044098.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-Based Drug Discovery. Weinheim: Wiley-VCH. p. 544. ISBN 9783527607495. Archived from the original on 8 September 2017.
  14. ^ US3091569A, Leonard, Sheffner Aaron, "Mucolytic-nu-acylated sulfhydryl compositions and process for treating animal mucus", issued 28 May 1963 
  15. ^ US patent 3091569, Aaron Leonard Sheffner, "Mucolytic-N-acylated sulfhydryl compositions and process for treating animal mucus", published 28 May 1963, issued 28 May 1963, assigned to Mead Johnson & Co 
  16. ^ World Health Organization Model List of Essential Medicines: 21st list 2019. Geneva: World Health Organization. 2019. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  17. ^ 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.
  18. ^ 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.
  19. ^ 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.
  20. ^ Lee BC, Dikiy A, Kim HY, Gladyshev VN (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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Acetylcysteine

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Acetylcysteine, also known as N-acetylcysteine (NAC), is a medication that is used to treat paracetamol overdose and to loosen thick mucus in individuals...

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Paracetamol poisoning

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not recommended. If there is a potential for toxicity, the antidote acetylcysteine is recommended. The medication is generally given for at least 24 hours...

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Glutathione

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glutathione at the level of cell membrane. The administration of N-acetylcysteine (NAC), a cysteine prodrug, helps replenish intracellular GSH levels...

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Acetylcysteinamide

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N-Acetylcysteine amide (abbrev. NACA, AD4 and also known as acetylcysteinamide) is an amide derivative of N-acetylcysteine that appears to have better...

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Acute liver failure

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The median time to death after admission was 5 days. Intravenous N-acetylcysteine has been found to be beneficial in acetaminophen toxicity but not in...

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Blepharitis

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with antibiotics and can reduce eyelid inflammation. The supplement n-acetylcysteine may be effective for blepharitis. Cunningham ET, Riordan-Eva P (2011-05-17)...

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Idiopathic pulmonary fibrosis

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reduced the risk of death by almost 50% over one year of treatment. N-Acetylcysteine (NAC) is a precursor to glutathione, an antioxidant. It has been hypothesized...

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Paracetamol

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hospital soon after the overdose. While the antidote, acetylcysteine (also called N-acetylcysteine or NAC), acts as a precursor for glutathione, helping...

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Mucoactive agent

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— Adams, Holland, & Bostwick, 2008, p. 591 Mucoactive drugs include: acetylcysteine ambroxol ammonium chloride bromhexine carbocisteine dornase alfa erdosteine...

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Amanita virosa

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DNA-dependent RNA polymerases, leading to an increase in RNA synthesis. N-acetylcysteine has shown promise in combination with other therapies. Animal studies...

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Nail biting

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randomized clinical trial in children and adolescents indicated that N-acetylcysteine, a glutathione and glutamate modulator, could, in the short term only...

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Amanita phalloides

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prednisolone—may be useful for the treatment of human amatoxin poisoning. N-Acetylcysteine has shown promise in combination with other therapies. Animal studies...

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Cysteine

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PMID 32808029. Kanter MZ (October 2006). "Comparison of oral and i.v. acetylcysteine in the treatment of acetaminophen poisoning". Am J Health Syst Pharm...

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Sulfur

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sulfonamides, known as sulfa drugs. A more recent example is mucolytic acetylcysteine. Sulfur is a part of many bacterial defense molecules. Most β-lactam...

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Eugenol

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dizziness, tachycardia (rapid heart rate), or acute kidney injury. N-acetylcysteine may be used to treat people with eugenol or clove oil overdose. Eugenol...

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Trichotillomania

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medication and robust evidence from high-quality studies is lacking. Acetylcysteine treatment stemmed from an understanding of glutamate's role in regulation...

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Isosorbide mononitrate

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presence of sulfhydryl groups in the muscle. The combination of oral N-acetylcysteine and a single dose of sustained-release isosorbide mononitrate 60 mg...

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Management of depression

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however. A systematic review and meta-analysis of 5 studies found that N-acetylcysteine reduces depressive symptoms more than placebo and has good tolerability...

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Atelectasis

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patients with cystic fibrosis and pneumonia, mucolytic agents such as acetylcysteine (NAC) is used. This nebulized treatment works by reducing mucous viscosity...

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Sildenafil

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(thionitrites): LA810 S-Nitrosoalbumin (SNALB) S-Nitrosated AR545C S-Nitroso-N-acetylcysteine (SNAC) S-Nitroso-N-acetylpenicillamine (SNAP) S-Nitroso-N-valerylpenicillamine...

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Influenza treatment

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medicines in influenza treatment details evidence suggesting that N-acetylcysteine, elderberry, or a combination of Eleutherococcus senticosus and Andrographis...

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Sepsis

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still occurs for other reasons. A 2012 Cochrane review concluded that N-acetylcysteine does not reduce mortality in those with SIRS or sepsis and may even...

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C5H9NO3S

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163.195 g/mol, exact mass: 163.0303 u) may refer to: Acetylcysteine, also known as N-acetylcysteine (NAC) Tiopronin This set index page lists chemical structure...

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Sodium thiosulfate

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et al. (2005). "Protection against Cisplatin-Induced Toxicities by N-Acetylcysteine and Sodium Thiosulfate as Assessed at the Molecular, Cellular, and in...

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Cerefolin

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contains L-methylfolate (as Metafolin) 5.6 mg, methylcobalamin 2 mg, N-acetylcysteine 600 mg. Cerefolin is a potentially harmful drug. Adverse effects can...

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Antioxidant

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body. Although large amounts of sulfur-containing amino acids such as acetylcysteine can increase glutathione, no evidence exists that eating high levels...

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Acetyl group

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including acetic acid, the neurotransmitter acetylcholine, acetyl-CoA, acetylcysteine, acetaminophen (also known as paracetamol), and acetylsalicylic acid...

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