Glutathione disulfide

Identification

Name
Glutathione disulfide
Accession Number
DB03310
Description

A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.

Type
Small Molecule
Groups
Approved, Experimental, Investigational
Structure
Thumb
Weight
Average: 612.631
Monoisotopic: 612.151961898
Chemical Formula
C20H32N6O12S2
Synonyms
  • Glutathione disulphide
  • GSSG
  • Oxidized glutathione
  • Oxiglutatione

Pharmacology

Indication
Not Available
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase Mu 2
activator
Humans
UGlutathione reductase, mitochondrial
substrate
Humans
UGlutathione peroxidaseNot Available
UMicrosomal glutathione S-transferase 1
activator
Humans
UGlutathione S-transferases (Cytosolic)
activator
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Purchasing individual compounds or compound libraries for your research?
Learn More
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Amo Endosol ExtraGlutathione disulfide (0.184 mg) + Calcium chloride (0.154 mg) + Dextrose, unspecified form (0.92 mg) + Magnesium chloride (0.2 mg) + Potassium chloride (0.38 mg) + Sodium bicarbonate (2.1 mg) + Sodium chloride (7.14 mg) + Sodium phosphate, dibasic (0.42 mg)Powder, for solutionIntraocularAmo Canada Company1993-12-312008-07-30Canada flag
Bss PlusGlutathione disulfide (4.6 mg/1mL) + Calcium chloride dihydrate (3.85 mg/1mL) + Dextrose, unspecified form (23 mg/1mL) + Magnesium chloride hexahydrate (5 mg/1mL) + Potassium chloride (0.395 mg/1mL) + Sodium bicarbonate (2.19 mg/1mL) + Sodium chloride (7.44 mg/1mL) + Sodium phosphate, dibasic, unspecified form (0.433 mg/1mL)OphthalmicALCON LABORATORIES, INC.2013-06-20Not applicableUS flag
Bss PlusGlutathione disulfide (0.0184 %) + Calcium chloride (0.0154 %) + Dextrose, unspecified form (0.092 %) + Magnesium chloride (0.02 %) + Potassium chloride (0.038 %) + Sodium bicarbonate (0.21 %) + Sodium chloride (0.714 %) + Sodium phosphate, dibasic (0.042 %)Kit; SolutionIntraocularAlcon, Inc.1982-12-31Not applicableCanada flag
NavstelGlutathione disulfide (0.184 mg) + Calcium chloride (0.154 mg) + Dextrose, unspecified form (0.92 mg) + Hypromellose (1.73 mg) + Magnesium chloride (0.2 g) + Potassium chloride (0.38 mg) + Sodium bicarbonate (2.1 mg) + Sodium chloride (7.14 mg) + Sodium phosphate, dibasic (0.42 mg)Kit; SolutionIntraocular; IrrigationAlcon, Inc.Not applicableNot applicableCanada flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
Tetracarboxylic acids and derivatives / N-acyl-alpha amino acids / L-alpha-amino acids / Dialkyldisulfides / Amino acids / Sulfenyl compounds / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids / Carboximidic acids / Organopnictogen compounds
show 4 more
Substituents
Aliphatic acyclic compound / Alpha peptide / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboximidic acid / Carboximidic acid derivative
show 20 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic disulfide, glutathione derivative (CHEBI:17858)

Chemical Identifiers

UNII
ULW86O013H
CAS number
27025-41-8
InChI Key
YPZRWBKMTBYPTK-BJDJZHNGSA-N
InChI
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
IUPAC Name
(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
SMILES
N[[email protected]@H](CCC(=O)N[[email protected]@H](CSSC[[email protected]](NC(=O)CC[[email protected]](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O

References

General References
Not Available
KEGG Drug
D00031
KEGG Compound
C00127
PubChem Compound
65359
PubChem Substance
46508372
ChemSpider
58835
BindingDB
225231
RxNav
25953
ChEBI
17858
ChEMBL
CHEMBL1372
ZINC
ZINC000003870129
PDBe Ligand
GDS
Wikipedia
Glutathione_disulfide
PDB Entries
1ykc / 2grt / 2wdu / 3fr3 / 3gx0 / 3m8u / 4c0r / 4f0b / 4f0c / 4is0
show 12 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentCataracts2
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentOvarian Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Powder, for solutionIntraocular
Kit; solutionIntraocular
Kit; solutionIntraocular; Irrigation
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7084130No2006-08-012021-11-29US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.406 mg/mLALOGPS
logP-3.6ALOGPS
logP-10ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)9.61ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area317.64 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity136.65 m3·mol-1ChemAxon
Polarizability58.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5623
Blood Brain Barrier+0.7907
Caco-2 permeable-0.7824
P-glycoprotein substrateSubstrate0.5058
P-glycoprotein inhibitor INon-inhibitor0.9122
P-glycoprotein inhibitor IINon-inhibitor0.9969
Renal organic cation transporterNon-inhibitor0.9418
CYP450 2C9 substrateNon-substrate0.9095
CYP450 2D6 substrateNon-substrate0.8077
CYP450 3A4 substrateNon-substrate0.7521
CYP450 1A2 substrateNon-inhibitor0.9373
CYP450 2C9 inhibitorNon-inhibitor0.8857
CYP450 2D6 inhibitorNon-inhibitor0.9399
CYP450 2C19 inhibitorNon-inhibitor0.8615
CYP450 3A4 inhibitorNon-inhibitor0.8874
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9907
Ames testAMES toxic0.6369
CarcinogenicityNon-carcinogens0.8726
BiodegradationReady biodegradable0.5845
Rat acute toxicity2.0571 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9765
hERG inhibition (predictor II)Non-inhibitor0.9422
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-c8147955c6b355f0fc5c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0910000000-3e6195d480fbfe87b449
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0292-1000291000-9683d81eec1eab3f9883
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01u0-8214980000-1738ea6e3b4537936eee
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-057i-9534520000-7ef32e723a98599c32d7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0147096000-e516803ef5124daee1a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-2497151000-ef5ab8f9bbe20555f37c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006y-9411230000-cc41719d1e717d214643
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0uki-0290000000-04456f914411a2ecbe4f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0039210000-772eee67ad10a2d98fa7
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-08fr-1957008000-f8812fd72d475ecd2693
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0000109000-65d563bcfc551b4a7abd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0003309000-7555effd0b74737b9d2f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0259201000-2cd328143ce713c285d9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05d0-0493000000-93bd088394049a484b9d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001r-0190000000-88b871b5a3f668f4b3a1
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0a59-0019811000-b24651cf6fc55de750b8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-053s-0495300000-69ab8e397b7a546ecd3f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-053r-0007920000-39da34018ceb610daa32
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0000009000-9cde769e8905f413f7e3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0000009000-4e3c9569882ab5507bf2
1H NMR Spectrum1D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Receptor binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTM2
Uniprot ID
P28161
Uniprot Name
Glutathione S-transferase Mu 2
Molecular Weight
25744.395 Da
References
  1. Aniya Y, Anders MW: Activation of rat liver microsomal glutathione S-transferase by reduced oxygen species. J Biol Chem. 1989 Feb 5;264(4):1998-2002. [PubMed:2492517]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nadp binding
Specific Function
Maintains high levels of reduced glutathione in the cytosol.
Gene Name
GSR
Uniprot ID
P00390
Uniprot Name
Glutathione reductase, mitochondrial
Molecular Weight
56256.565 Da
References
  1. Tamura T, McMicken HW, Smith CV, Hansen TN: Mitochondrial targeting of glutathione reductase requires a leader sequence. Biochem Biophys Res Commun. 1996 May 24;222(3):659-63. doi: 10.1006/bbrc.1996.0800. [PubMed:8651901]
Kind
Protein group
Organism
Not Available
Pharmacological action
Unknown
General Function
Glutathione peroxidase activity
Specific Function
Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione. May constitute a glutathione peroxidas...

Components:
References
  1. Heyob KM, Rogers LK, Welty SE: Glutathione reductase targeted to type II cells does not protect mice from hyperoxic lung injury. Am J Respir Cell Mol Biol. 2008 Dec;39(6):683-8. doi: 10.1165/rcmb.2008-0112OC. Epub 2008 Jun 19. [PubMed:18566333]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a wide substrate specificity.
Gene Name
MGST1
Uniprot ID
P10620
Uniprot Name
Microsomal glutathione S-transferase 1
Molecular Weight
17598.45 Da
References
  1. Aniya Y, Anders MW: Activation of rat liver microsomal glutathione S-transferase by reduced oxygen species. J Biol Chem. 1989 Feb 5;264(4):1998-2002. [PubMed:2492517]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.

Components:
References
  1. Aniya Y, Anders MW: Activation of rat liver microsomal glutathione S-transferase by reduced oxygen species. J Biol Chem. 1989 Feb 5;264(4):1998-2002. [PubMed:2492517]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates