N-Acetylcysteine amide

Uses

N-acetylcysteine amide has been used:

• to protect retinal pigment epithelium (RPE) from oxidative stress
• to show that increased expression of cell adhesion molecule 4 (CADM4) in oligodendrocytes inhibits myelination
• to protect cells from apoptosis induced by shikonin plus erlotinib/gefitinib
• as a component in various culture media

Preparation

N-Acetyl-L-cysteine methyl ester (10 g) under a flush of nitrogen was treated with ammonium hydroxide (28% aqueous, 66 mL) over 10 minutes at room temperature and stirred for 6 hours. The resulting solution was concentrated in vacuo and ethanol (100 mL) was added. Then the solution was concentrated again under reduced pressure at 48 00 then subjected to high vacuum overnight to afford N-acetylcysteine amide as a white crystalline solid.

Biochem/physiol Actions

N-acetylcysteine amide is a membrane penetrating antioxidant with antiinflamatory activity through regulation of activation of NF-κB and HIF-1α as well as modulation of ROS. The compound readily crosses cell membranes, replenishes intracellular GSH, and defends the cell from oxidative stress. In contrast to DTT, AD4 is able to directly reduce intracellularl GSSG to GSH without the involvement of glutathione peroxidase. Such direct thiol exchange might have a protective effect. This compound has a potential in research and exploration for treatment of neurodegeneration, radiation exposure, and other oxidation-mediated disorders.

Clinical Use

N-Acetylcysteine amide has antioxidant and is often used in the preparation of Eyedrops. It has been used as a treatment for the prevention or healing of cataracts, macular degeneration, and other degenerative eye disorders.