N-Acetylcysteine ethyl ester

N-Acetylcysteine ethyl ester
Clinical data
Drug classAntioxidant
Identifiers
  • ethyl (2R)-2-acetamido-3-sulfanylpropanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC7H13NO3S
Molar mass191.25 g·mol−1
3D model (JSmol)
  • CCOC(=O)[C@H](CS)NC(=O)C
  • InChI=1S/C7H13NO3S/c1-3-11-7(10)6(4-12)8-5(2)9/h6,12H,3-4H2,1-2H3,(H,8,9)/t6-/m0/s1
  • Key:MSMRAGNKRYVTCX-LURJTMIESA-N

N-Acetylcysteine ethyl ester (NACET, NAC-Et) is an antioxidant which acts as a lipophilic prodrug for N-acetylcysteine and subsequently glutathione, with improved bioavailability over N-acetylcysteine itself, and has been researched in animal studies as a potential treatment for diabetic retinopathy.[1][2][3][4][5] It has also been sold as a "dietary supplement" in combination with glycine under the name GlyNAC-Et as a supposedly improved version of the older glycine-NAC combination GlyNAC which has been claimed to show efficacy in counteracting symptoms associated with aging as well as HIV infection, diabetes and nerve damage.[6][7][8][9][10][11][12] Several related compounds such as γ-glutamylcysteine ethyl ester and glutathione ethyl ester have been investigated for similar applications.[13][14][15]

References

  1. ^ Giustarini D, Milzani A, Dalle-Donne I, Tsikas D, Rossi R (December 2012). "N-Acetylcysteine ethyl ester (NACET): a novel lipophilic cell-permeable cysteine derivative with an unusual pharmacokinetic feature and remarkable antioxidant potential". Biochemical Pharmacology. 84 (11): 1522–1533. doi:10.1016/j.bcp.2012.09.010. PMID 23000913.
  2. ^ Giustarini D, Galvagni F, Dalle Donne I, Milzani A, Severi FM, Santucci A, et al. (October 2018). "N-acetylcysteine ethyl ester as GSH enhancer in human primary endothelial cells: A comparative study with other drugs". Free Radical Biology & Medicine. 126: 202–209. doi:10.1016/j.freeradbiomed.2018.08.013. hdl:11365/1061971. PMID 30114478.
  3. ^ Kularatne RN, Bulumulla C, Catchpole T, Takacs A, Christie A, Stefan MC, et al. (May 2020). "Protection of human retinal pigment epithelial cells from oxidative damage using cysteine prodrugs". Free Radical Biology & Medicine. 152: 386–394. doi:10.1016/j.freeradbiomed.2020.03.024. PMID 32229256.
  4. ^ Tosi GM, Giustarini D, Franci L, Minetti A, Imperatore F, Caldi E, et al. (January 2021). "Superior Properties of N-Acetylcysteine Ethyl Ester over N-Acetyl Cysteine to Prevent Retinal Pigment Epithelial Cells Oxidative Damage". International Journal of Molecular Sciences. 22 (2): 600. doi:10.3390/ijms22020600. PMC 7827200. PMID 33435325.
  5. ^ Realini G, Amato R, Rasa M, Ceccatelli R, Cannavale A, Bottoni L, et al. (December 2025). "N-acetyl-l-cysteine ethyl ester (NACET) induces the transcription factor NRF2 and prevents retinal aging and diabetic retinopathy". Redox Biology. 88 103914. doi:10.1016/j.redox.2025.103914. PMC 12793733. PMID 41205411.
  6. ^ Kumar P, Liu C, Hsu JW, Chacko S, Minard C, Jahoor F, et al. (March 2021). "Glycine and N-acetylcysteine (GlyNAC) supplementation in older adults improves glutathione deficiency, oxidative stress, mitochondrial dysfunction, inflammation, insulin resistance, endothelial dysfunction, genotoxicity, muscle strength, and cognition: Results of a pilot clinical trial". Clinical and Translational Medicine. 11 (3) e372. doi:10.1002/ctm2.372. PMC 8002905. PMID 33783984.
  7. ^ Sekhar RV (December 2021). "GlyNAC Supplementation Improves Glutathione Deficiency, Oxidative Stress, Mitochondrial Dysfunction, Inflammation, Aging Hallmarks, Metabolic Defects, Muscle Strength, Cognitive Decline, and Body Composition: Implications for Healthy Aging". The Journal of Nutrition. 151 (12): 3606–3616. doi:10.1093/jn/nxab309. PMID 34587244.
  8. ^ Sekhar RV (January 2022). "GlyNAC (Glycine and N-Acetylcysteine) Supplementation Improves Impaired Mitochondrial Fuel Oxidation and Lowers Insulin Resistance in Patients with Type 2 Diabetes: Results of a Pilot Study". Antioxidants. 11 (1): 154. doi:10.3390/antiox11010154. PMC 8773349. PMID 35052658.
  9. ^ Kumar P, Liu C, Suliburk J, Hsu JW, Muthupillai R, Jahoor F, et al. (January 2023). "Supplementing Glycine and N-Acetylcysteine (GlyNAC) in Older Adults Improves Glutathione Deficiency, Oxidative Stress, Mitochondrial Dysfunction, Inflammation, Physical Function, and Aging Hallmarks: A Randomized Clinical Trial". The Journals of Gerontology. Series A, Biological Sciences and Medical Sciences. 78 (1): 75–89. doi:10.1093/gerona/glac135. PMC 9879756. PMID 35975308.
  10. ^ Xu X, Zhang CJ, Talifu Z, Liu WB, Li ZH, Wang XX, et al. (April 2024). "The Effect of Glycine and N-Acetylcysteine on Oxidative Stress in the Spinal Cord and Skeletal Muscle After Spinal Cord Injury". Inflammation. 47 (2): 557–571. doi:10.1007/s10753-023-01929-9. PMC 11074018. PMID 37975960.
  11. ^ Broome SC, Whitfield J, Karagounis LG, Hawley JA (September 2024). "Mitochondria as Nutritional Targets to Maintain Muscle Health and Physical Function During Ageing". Sports Medicine. 54 (9): 2291–2309. doi:10.1007/s40279-024-02072-7. PMC 11393155. PMID 39060742.
  12. ^ Nicoletti GR, Mangano K, Nicoletti F, Cavalli E (December 2025). "From Elixirs to Geroscience: A Historical and Molecular Perspective on Anti-Aging Medicine". Molecules. 30 (24): 4728. doi:10.3390/molecules30244728. PMC 12735892. PMID 41471752.
  13. ^ Pocernich CB, Butterfield DA (May 2012). "Elevation of glutathione as a therapeutic strategy in Alzheimer disease". Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease. 1822 (5): 625–630. doi:10.1016/j.bbadis.2011.10.003. PMC 3277671. PMID 22015471.
  14. ^ Rice B, Overbay J, Sebastian A, Sullivan PG, Reed TT (September 2025). "Restoration of Enzymatic Activity of Energy-Related Proteins in Rats with Traumatic Brain Injury Following Administration of Gamma-Glutamylcysteine Ethyl Ester". Brain Sciences. 15 (10): 1067. doi:10.3390/brainsci15101067. PMC 12563604. PMID 41154162.
  15. ^ Guo J, Li Z, Wang J, Ma B, Zhang L, Wang H, et al. (November 2025). "In Situ Evaluation of the GSH Depletion Ability of Various Alkylating Agents and the Protective Effect of Several Active Thiol Compounds Based on High-Content Cell Analysis". Toxics. 13 (12): 1016. Bibcode:2025Toxic..13.1016G. doi:10.3390/toxics13121016. PMC 12737281. PMID 41441237.
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