Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H32N6O12S2 |
| Molecular Weight | 612.631 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
InChI
InChIKey=YPZRWBKMTBYPTK-BJDJZHNGSA-N
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
DescriptionCurator's Comment: description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022193lbl.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/6137189
Curator's Comment: description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022193lbl.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/6137189
Oxiglutathione is the oxidized disulfide form of glutathione (GSH) with potential protective activity. Glutathione disulfide (GSSG) is reduced by glutathione reductase to GSH. GSSG and GSH together play important roles in numerous redox reactions, such as those involved in the detoxification of harmful substances and free radicals, and in reactions preventing oxidative damage in erythrocytes. Upon ocular administration in irrigation solution, glutathione disulfide may exert a beneficial effect on the intracellular redox state of glutathione, thereby protecting the integrity and barrier function of the corneal endothelial cells.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2755 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | NAVSTEL Approved UseNavstel is a sterile intraocular irrigating solution for use during all surgical procedures, including those requiring a relatively long intraocular perfusion time (e.g. vitrectomy, extracapsular cataract extraction/lens aspiration, anterior segment reconstruction, etc.). Upon ocular administration in irrigation solution, oxiglutathione disulfide exerts a beneficial effect on the intracellular redox state of glutathione, thereby protecting the integrity and barrier function of the corneal endothelial cells. Launch Date2008 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.65 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20359856/ |
250 mg/kg single, intraperitoneal dose: 250 mg/kg route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
OXIGLUTATIONE plasma | Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.18 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20359856/ |
250 mg/kg single, intraperitoneal dose: 250 mg/kg route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
OXIGLUTATIONE plasma | Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20359856/ |
250 mg/kg single, intraperitoneal dose: 250 mg/kg route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
OXIGLUTATIONE plasma | Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
Other AEs: Increased intraocular pressure, Headache... Other AEs: Increased intraocular pressure (12%) Sources: Headache (3%) Ocular discomfort (5%) Macular edema (4%) Conjunctival hyperemia (4%) Dry eye (3%) Iritis (3%) Retinal hemorrhage (3%) Vision blurred (2%) Posterior capsule opacification (2%) Cataract (11%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Cataract | 11% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Increased intraocular pressure | 12% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Posterior capsule opacification | 2% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Vision blurred | 2% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Dry eye | 3% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Headache | 3% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Iritis | 3% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Retinal hemorrhage | 3% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Conjunctival hyperemia | 4% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Macular edema | 4% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
| Ocular discomfort | 5% | 10 mL single, intraocular Dose: 10 mL Route: intraocular Route: single Dose: 10 mL Co-administed with:: hypromellose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) Sources: dextrose(10 mL or 20 mL of intraocular irrigating solution (each mL contains: calcium chloride, magnesium chloride, dextrose, gluthathione disulfide (oxidized glutathione))) |
unhealthy Health Status: unhealthy Condition: surgical procedures Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Time-dependent oxidative stress caused by benznidazole. | 2001 |
|
| Melatonin, a pineal secretory product with antioxidant properties, protects against cisplatin-induced nephrotoxicity in rats. | 2001 Apr |
|
| Effects of R- and S-apomorphine on MPTP-induced nigro-striatal dopamine neuronal loss. | 2001 Apr |
|
| Modulation of ceramide-induced NF-kappaB binding activity and apoptotic response by caffeic acid in U937 cells: comparison with other antioxidants. | 2001 Apr 1 |
|
| Oxidative modification of H-ras: S-thiolation and S-nitrosylation of reactive cysteines. | 2001 Apr 1 |
|
| Effects of aging on the susceptibility to the toxic effects of cyclosporin A in rats. Changes in liver glutathione and antioxidant enzymes. | 2001 Apr 15 |
|
| Non-enzymatic antioxidative defence mechanisms against reactive oxygen species in bovine-retained and not-retained placenta: vitamin C and glutathione. | 2001 Aug |
|
| Crayfish Procambarus clarkii shows circadian variations in different parameters of the GSH cycle. | 2001 Aug |
|
| Protective effect of melatonin against adriamycin toxicity in the rat. | 2001 Aug |
|
| A comparative study of glutathione and ascorbate metabolism during germination of Pinus pinea L. seeds. | 2001 Aug |
|
| Determination of blood total, reduced, and oxidized glutathione in pediatric subjects. | 2001 Aug |
|
| Vascular and hepatocellular peroxynitrite formation during acetaminophen toxicity: role of mitochondrial oxidant stress. | 2001 Aug |
|
| An ion exchange liquid chromatography/mass spectrometry method for the determination of reduced and oxidized glutathione and glutathione conjugates in hepatocytes. | 2001 Aug |
|
| Human immunodeficiency virus type 1 Tat protein impairs selenoglutathione peroxidase expression and activity by a mechanism independent of cellular selenium uptake: consequences on cellular resistance to UV-A radiation. | 2001 Feb 15 |
|
| In vivo and in vitro influence of selenium on DNA/RNA synthesis in spleen and lymphocytes in culture--possible mediation of changes in GSH/GSSG ratio. | 2001 Jan |
|
| Analysis of glutathione by capillary electrophoresis based on sample stacking. | 2001 Jul |
|
| Effects of chronic N-acetylcysteine treatment on the actions of peroxynitrite on aortic vascular reactivity in hypertensive rats. | 2001 Jul |
|
| Thiols prevent H2O2-mediated loss of sperm motility in cryopreserved bull semen. | 2001 Jul 15 |
|
| Influences of glutathione on anionic substrate efflux in tumour cells expressing the multidrug resistance-associated protein, MRP1. | 2001 Jul 15 |
|
| Oxidative stress in zebrafish cells: potential utility of transgenic zebrafish as a deployable sentinel for site hazard ranking. | 2001 Jul 2 |
|
| Modulation of rat liver mitochondrial antioxidant defence system by thyroid hormone. | 2001 Jul 27 |
|
| Regulation of the plant-type 5'-adenylyl sulfate reductase by oxidative stress. | 2001 Jul 31 |
|
| Potential mechanisms for the inhibition of tumor cell growth by manganese superoxide dismutase. | 2001 Jun |
|
| Lack of protective effect by intermittent hypoxia on MPTP-induced neurotoxicity in mice. | 2001 Jun |
|
| A possible role of glutathione and glutathione disulfide in tracheary element differentiation in the cultured mesophyll cells of Zinnia elegans. | 2001 Jun |
|
| Hydrogen peroxide removal and glutathione mixed disulfide formation during metabolic inhibition in mesencephalic cultures. | 2001 Jun |
|
| Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells. | 2001 Jun |
|
| Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. | 2001 Jun 1 |
|
| Metabolism of S-nitrosoglutathione in intact mitochondria. | 2001 Jun 1 |
|
| Benzo(a)pyrene-coated onto Fe(2)O(3) particles-induced lung tissue injury: role of free radicals. | 2001 Jun 10 |
|
| Characterization of glutathione amide reductase from Chromatium gracile. Identification of a novel thiol peroxidase (Prx/Grx) fueled by glutathione amide redox cycling. | 2001 Jun 15 |
|
| Thiram-induced cytotoxicity is accompanied by a rapid and drastic oxidation of reduced glutathione with consecutive lipid peroxidation and cell death. | 2001 Jun 21 |
|
| Redox-dependent modulation of lipid synthesis induced by oleic acid in the human intestinal epithelial cell line Caco-2. | 2001 Mar |
|
| Effect of the glutathione/glutathione disulfide redox couple on thiopurine methyltransferase. | 2001 Mar 15 |
|
| Putative disulfide-forming pathway of porcine insulin precursor during its refolding in vitro. | 2001 Mar 6 |
|
| Glutathione deficiency intensifies ischaemia-reperfusion induced cardiac dysfunction and oxidative stress. | 2001 May |
|
| Regulation of LPS induced IL-12 production by IFN-gamma and IL-4 through intracellular glutathione status in human alveolar macrophages. | 2001 May |
|
| Calorie restriction attenuates inflammatory responses to myocardial ischemia-reperfusion injury. | 2001 May |
|
| Differential antioxidant enzyme activities and glutathione content between rat and rabbit conceptuses. | 2001 May 15 |
|
| Glutathiolation of the proteasome is enhanced by proteolytic inhibitors. | 2001 May 15 |
|
| Effect of DL-alpha-lipoic acid on mitochondrial enzymes in aged rats. | 2001 Nov 28 |
|
| Induction of mild intracellular redox imbalance inhibits proliferation of CaCo-2 cells. | 2001 Oct |
|
| Glutathione stability in whole blood: effects of various deproteinizing acids. | 2001 Oct |
|
| The functions of inter- and intracellular glutathione transport systems in plants. | 2001 Oct |
|
| Redox regulation of endothelial barrier integrity. | 2001 Oct |
|
| COPD as a muscle disease. | 2001 Oct 1 |
|
| Redox-mediated effects of selenium on apoptosis and cell cycle in the LNCaP human prostate cancer cell line. | 2001 Oct 1 |
|
| Differences in basal airway antioxidant concentrations are not predictive of individual responsiveness to ozone: a comparison of healthy and mild asthmatic subjects. | 2001 Oct 15 |
|
| Application of double-impedance system and cyclic voltammetry to study the adsorption of fullerols (C60(OH)n) on biological peptide-adsorbed gold electrode. | 2001 Sep |
|
| Inhibition of rat PC12 cell calpain activity by glutathione, oxidized glutathione and nitric oxide. | 2001 Sep 28 |
Patents
Sample Use Guides
NAVSTEL solution, should be used according to the standard technique employed by the operating surgeon. Do not use NAVSTEL until Part I is fully reconstituted with Part II. Reconstitute just prior to surgery. After reconstitution, use a single patient administration set with an air-inlet in the plastic spike since the bottle does not contain a separate airway tube. Follow the directions for the particular administration set to be used. Insert the spike aseptically into the bottle through the center target area of the rubber stopper. Allow the fluid to flow to remove air from the tubing before intraocular irrigation begins. If a second bottle is necessary to complete the surgical procedure, insure that the vacuum is vented from the second bottle BEFORE attachment to the administration set.
Route of Administration:
Irrigation
Kinetic studies were carried out at 25 °C in a volume of 1 mL. The assay mixtures contained 100 mM potassium phosphate buffer pH 7.0, 200 mM KCl, 100 uM NADPH, and 1 mM GSSG. Inhibitor stock solutions were prepared in 100% DMSO. One % final DMSO concentration was kept constant in the assay cuvette. The reaction was started with the addition of the enzyme (8 milliunits or 1.2 pmol of FAD-containing subunit in 5 uL aliquot), and initial rates were determined from NADPH oxidation measured at 340 nm. Km for GSSG reduction was found to be 12.5 uM.
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NCI_THESAURUS |
C26170
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m5781
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5130
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C62624
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65359
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ULW86O013H
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DTXSID5048972
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CHEMBL1372
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GLUTATHIONE DISULFIDE
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100000087102
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6698
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
