Acetylcysteinamide
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| ECHA InfoCard | 100.211.696 |
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| Formula | C5H10N2O2S |
| Molar mass | 162.21 g·mol−1 |
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| Density | 1.227 g/cm3 |
| Boiling point | 308 °C (586 °F) |
| Solubility in water | 22 mg/mL (20 °C) |
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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 blood–brain barrier permeability and bioavailability possessing potential antioxidant and anti-inflammatory activity[1][2]
When administered, N-acetylcysteine amide (NACA) increases glutathione levels. Glutathione neutralizes reactive oxygen species, reduces oxidative stress, and prevents induced cell damage and apoptosis. NACA has increased lipophilicity and membrane permeability compared to NAC (N-acetylcysteine).[2]
Toxicity
N-acetylcysteine is acutely toxic when taken orally.[2]
chemical designation
This compound belongs to a class of experimental compounds known as n-acyl-alpha-amino acids and their derivatives. These are compounds containing an alpha-amino acid (or its derivative) with an acyl group on the terminal nitrogen atom.[3]
pharmacokinetics and pharmacodynamics
The pharmacokinetics of N-Acetylcysteine amide remain unclear or unstudied.
N-acetylcysteineamide (NACA) is an amide derivative of N-acetylcysteine (NAC) that is rapidly converted to NAC after systemic administration.
The bioavailability of NACA is significantly higher than NAC (67% and 15%,).[4]
Its mechanism of action involves replenishment of GSH (glutathione), a major antioxidant, and direct neutralization of reactive oxygen species.[5]
References
- ^ Sunitha K, Hemshekhar M, Thushara RM, Santhosh MS, Yariswamy M, Kemparaju K, et al. (May 2013). "N-Acetylcysteine amide: a derivative to fulfill the promises of N-Acetylcysteine". Free Radical Research. 47 (5): 357–367. doi:10.3109/10715762.2013.781595. PMID 23472882. S2CID 207517783.
- ^ a b c "N-Acetylcysteine amide". PubChem. U.S. National Library of Medicine. Retrieved 2025-09-13.
- ^ "Acetylcysteine amide". go.drugbank.com. Retrieved 2025-09-09.
- ^ He R, Zheng W, Ginman T, Ottosson H, Norgren S, Zhao Y, et al. (February 2020). "Pharmacokinetic profile of N-acetylcysteine amide and its main metabolite in mice using new analytical method". European Journal of Pharmaceutical Sciences. 143 105158. doi:10.1016/j.ejps.2019.105158. PMID 31740394.
- ^ He R, Zheng W, Ginman T, Ottosson H, Norgren S, Zhao Y, et al. (2020-02-15). "Pharmacokinetic profile of N-acetylcysteine amide and its main metabolite in mice using new analytical method". European Journal of Pharmaceutical Sciences. 143 105158. doi:10.1016/j.ejps.2019.105158. ISSN 0928-0987. PMID 31740394.