Glutathione disulfide

Identification

Name
Glutathione disulfide
Accession Number
DB03310  (EXPT01575, DB09544)
Type
Small Molecule
Groups
Approved, Experimental, Investigational
Description

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

Structure
Thumb
Synonyms
  • Glutathione disulphide
  • GSSG
  • Oxidized glutathione
  • Oxiglutatione
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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 Chloride (7.14 mg) + Sodium bicarbonate (2.1 mg) + Sodium phosphate, dibasic (0.42 mg)Powder, for solutionIntraocularAmo Canada Company1993-12-312008-07-30Canada
Bss PlusGlutathione disulfide (0.0184 %) + Calcium Chloride (0.0154 %) + Dextrose, unspecified form (0.092 %) + Magnesium chloride (0.02 %) + Potassium Chloride (0.038 %) + Sodium Chloride (0.714 %) + Sodium bicarbonate (0.21 %) + Sodium phosphate, dibasic (0.042 %)Kit; SolutionIntraocularAlcon, Inc.1982-12-31Not applicableCanada
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 Chloride (7.44 mg/1mL) + Sodium bicarbonate (2.19 mg/1mL) + Sodium phosphate, dibasic, unspecified form (0.433 mg/1mL)KitAlcon, Inc.1982-06-28Not applicableUs
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 Chloride (7.14 mg) + Sodium bicarbonate (2.1 mg) + Sodium phosphate, dibasic (0.42 mg)Kit; SolutionIntraocular; IrrigationAlcon, Inc.Not applicableNot applicableCanada
Categories
UNII
ULW86O013H
CAS number
27025-41-8
Weight
Average: 612.631
Monoisotopic: 612.151961898
Chemical Formula
C20H32N6O12S2
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[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

Pharmacology

Indication
Not Available
Associated Therapies
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase Mu 2Not AvailableHuman
UGlutathione reductase, mitochondrialNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D00031
KEGG Compound
C00127
PubChem Compound
65359
PubChem Substance
46508372
ChemSpider
58835
BindingDB
225231
ChEBI
17858
ChEMBL
CHEMBL1372
HET
GDS
Wikipedia
Glutathione_disulfide
PDB Entries
1ykc / 2grt / 2wdu / 3fr3 / 3gx0 / 3m8u / 4c0r / 4f0b / 4f0c / 4is0
show 11 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCancer, Breast1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Powder, for solutionIntraocular
Kit
Kit; solutionIntraocular
Kit; solutionIntraocular; Irrigation
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7084130No2006-08-012021-11-29Us

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

Taxonomy

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
Alpha peptide / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Tetracarboxylic acid or derivatives / Alpha-amino acid / Alpha-amino acid or derivatives / L-alpha-amino acid / Amino acid or derivatives / Amino acid / Dialkyldisulfide
show 20 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic disulfide, glutathione derivative (CHEBI:17858)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:33