Research Brief
Glutathione: Chemical Properties
20 Citacoes PubMedRevisado por EspecialistasCertificado GMPUltima Revisao: julho de 2026
Propriedades Quimicas
| Molecular Formula | C₁₀H₁₇N₃O₆S |
| Molecular Weight | 307.32 g/mol |
| CAS Number | 70-18-8 |
| PubChem CID | 124886 |
| Sequence (3-Letter) | γ-Glu-Cys-Gly |
| Sequence (1-Letter) | γ-E-C-G |
| IUPAC Name | (2S)-2-Amino-5-({(2R)-1-[(carboxymethyl)amino]-1-oxo-3-sulfanylpropan-2-yl}amino)-5-oxopentanoic acid |
| Structure | Tripeptide with gamma-peptide linkage between γ-carboxyl of glutamate and α-amino of cysteine; contem free thiol (sulfhydryl) group; forms intermolecular disulfide bond (GSSG) upon oxidation |
| Origin | Endogenous tripeptide sintetizado(a) em virtually all mammalian cells from L-glutamate, L-cysteine, and glycine via a two-step ATP-dependent enzymatic process (GCL and GS) |
| Classification | Endogenous Tripeptide Antioxidant / Redox Modulator / Research Compound |
| Half-Life | Plasma meia-vida < 3 minutes (IV administration); intracellular turnover regulado(a) por γ-glutamyl cycle |
| Bioavailability | Low oral biodisponibilidade due to intestinal hidrolise by γ-glutamyl transpeptidase (GGT); aprimorou by liposomal or sublingual delivery |
Identificadores
| Purity Standard | ≥98% by HPLC |
| Synonyms | GSH, L-Glutathione, Reduced Glutathione, γ-L-glutamyl-L-cysteinylglycine, Isethion, Tathione, Glutatiol |
| InChI Key | RWSXRVCMGQZWBV-WDSKDSINSA-N |
| SMILES | N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O |
| InChI | InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1 |
Referencias
- Allen J, Bradley RD. Effects of oral glutathione supplementation on sistemico(a) estresse oxidativo biomarcadors in human volunteers. Journal of Alternative and Complementary Medicine, 17(9), 827-833, 2011.
- Arjinpathana N, Asawanonda P. Glutathione como um(a) oral whitening agent: a randomizado, duplo-cego, controlado por placebo study. Journal of Dermatological Treatment, 23(2), 97-102, 2012.
- Ballatori N, Krance SM, Notenboom S, Shi S, Tieu K, Hammond CL. Glutathione dysregulacao e o(a) etiology and progression of human diseases. Biological Chemistry, 390(3), 191-214, 2009.
- Cascinu S, Cordella L, Del Ferro E, et al. Neuroprotective effect of reduziu glutathione on cisplatin-based chemotherapy in advanced gastric cancer: a randomizado, duplo-cego, controlado por placebo trial. Journal of Clinical Oncology, 13(1), 26-32, 1995.
- Chinta SJ, Kumar MJ, Hsu M, et al. Inducible alterations of glutathione levels in adult dopaminergic midbrain neurons result in nigrostriatal degeneration. Journal of Neuroscience, 27(51), 13997-14006, 2007.
- Handog EB, Datuin MS, Singzon IA. An open-label, single-arm trial of a seguranca and efficacy of um(a) novo(a) preparation of glutathione como um(a) skin-lightening agent in Filipino women. International Journal of Dermatology, 55(2), 153-157, 2016.
- Holmay MJ, Terpstra M, Coles LD, et al. N-Acetylcysteine boosts brain and blood glutathione in Gaucher and Parkinson diseases. Clinical Neuropharmacology, 36(4), 103-106, 2013.
- Honda Y, Kessoku T, Sumida Y, et al. Efficacy of glutathione for o tratamento of nonalcoholic fatty doenca hepatico(a)a: an open-label, single-arm, multicenter, pilot study. BMC Gastroenterology, 17(1), 96, 2017.
- Kovacs-Nolan J, Rupa P, Matsui T, et al. In vitro and ex vivo uptake of glutathione (GSH) atraves do(a) intestinal epithelium and fate of oral GSH after in vivo supplementation. Journal of Agricultural and Food Chemistry, 62(39), 9499-9506, 2014.
- Lenzi A, Culasso F, Gandini L, Lombardo F, Dondero F. Placebo-controlled, duplo-cego, cross-over trial of glutathione therapy in male infertility. Human Reproduction, 8(10), 1657-62, 1993.
- Mischley LK, Leverenz JB, Lau RC, et al. A randomizado, duplo-cego phase I/IIa study of intranasal glutathione in Parkinson's disease. Movement Disorders, 30(12), 1696-1701, 2015.
- Richie JP, Nichenametla S, Neidig W, et al. Randomized controlled trial of oral glutathione supplementation on body stores of glutathione. European Journal of Nutrition, 54(2), 251-263, 2015.
- Sechi G, Deledda MG, Bua G, et al. Reduced intravenoso(a) glutathione in o tratamento of precoce Parkinson's disease. Progress in Neuro-Psychopharmacology and Biological Psychiatry, 20(7), 1159-1170, 1996.
- Sinha R, Sinha I, Calcagnotto A, et al. Oral supplementation with liposomal glutathione elevates body stores of glutathione and markers of funcao imunologica. European Journal of Clinical Nutrition, 72(1), 105-111, 2018.
- Smyth JF, Bowman A, Perren T, et al. Glutathione reduz the toxicity and melhora qualidade de vida of women diagnosed with ovarian cancer treated with cisplatin: results of a duplo-cego, randomised trial. Annals of Oncology, 8(6), 569-73, 1997.
- Søndergård SD, Cintin I, Kuhlman AB, et al. The effects of 3 weeks of oral glutathione supplementation on whole body sensibilidade a insulina in obese males with and sem diabetes tipo 2: a randomizado trial. Applied Physiology, Nutrition, and Metabolism, 46(9), 1133-1142, 2021.
- Visca A, Bishop CT, Hilton S, Hudson VM. Oral reduziu L-glutathione melhora growth in pediatric cystic fibrose patients. Journal of Pediatric Gastroenterology and Nutrition, 60(6), 802-810, 2015.
- Watanabe F, Hashizume E, Chan GP, Kamimura A. Skin-whitening and skin-condition-improving effects of topico(a) oxidized glutathione: a duplo-cego and controlado por placebo ensaio clinico in healthy women. Clinical, Cosmetic and Investigational Dermatology, 7, 267-274, 2014.
- Weschawalit S, Thongthip S, Phutrakool P, Asawanonda P. Glutathione e seu(sua) antiaging and antimelanogenic effects. Clinical, Cosmetic and Investigational Dermatology, 10, 147-153, 2017.
- Witschi A, Reddy S, Stofer B, Lauterburg BH. The sistemico(a) availability of oral glutathione. European Journal of Clinical Pharmacology, 43(6), 667-669, 1992.
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