U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H17N3O6S
Molecular Weight 307.325
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUTATHIONE

SMILES

C(CC(=N[C@@]([H])(CS)C(=NCC(=O)O)O)O)[C@@]([H])(C(=O)O)N

InChI

InChIKey=RWSXRVCMGQZWBV-WDSKDSINSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23036594 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3ef475c9-7938-4870-b336-fb0c2dafb3cd | https://clinicaltrials.gov/ct2/show/NCT01450267

Glutathione (GSH, also called as reduced glutathione) is a tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes such as, glutathione reductase, glutathione peroxidases, peroxiredoxins. Glutathione S-transferases catalyse the conjugation of GSH via a sulfhydryl group to electrophilic centers on a wide variety of substrates in order to make the compounds more water-soluble. As a part of homeopathic product, glutathione is used for temporary relief of symptoms related to Free Radical Toxicity including tingling in hands and feet, mood changes, frequent colds, poor digestion, fatigue, and constipation. In addition, for temporary relief of pain in the back from urinating, constant urging and frequent urination, kidneys sensitive to pressure, and pain from back extending down the thigh. Glutathione is an important nutrient for brain function and loss of glutathione has been implicated in Parkinson's disease. In phase II of the clinical trial was investigated whether administration of either dose of glutathione, as a nasal spray, improves PD symptoms over time in a population of individuals with Parkinson's disease (PD). In addition in phase II of clinical trial was shown, that reduced glutathione, an ingredient of RayGel™, has been helpful in decreasing some radiation therapy side effects to the skin. Reduced glutathione plays a vital role in both making DNA and cell repair. Cystic fibrosis (CF) is the most common inherited disease among the Caucasian population with considerable morbidity and reduced life expectancy. Glutathione (GSH) represents the first-line defence of the lung against oxidative stress-induced cell injury. Therapeutic approaches with inhaled GSH could improve the reduced lung antioxidant capacity in order to counterbalance the oxidant stress linked to the chronic airway inflammation and bacterial infection.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Glutathione S-transferases
Target ID: P00390
Gene ID: 2936.0
Gene Symbol: GSR
Target Organism: Homo sapiens (Human)
Target ID: Glutathione peroxidases
Conditions
PubMed

PubMed

TitleDatePubMed
Contribution of the mesangium to elastic strength and anchorage of the glomerular capillary tuft.
2001
Detection of phosphorylation-dependent interactions by far-western gel overlay.
2001
Perturbation of the pore of the cystic fibrosis transmembrane conductance regulator (CFTR) inhibits its atpase activity.
2001 Apr 13
A rice functional transcriptional activator, RISBZ1, responsible for endosperm-specific expression of storage protein genes through GCN4 motif.
2001 Apr 27
Localization of the C-terminus of rat glutathione S-transferase A1-1: crystal structure of mutants W21F and W21F/F220Y.
2001 Feb 1
High sensitivity of Nrf2 knockout mice to acetaminophen hepatotoxicity associated with decreased expression of ARE-regulated drug metabolizing enzymes and antioxidant genes.
2001 Jan
Effects of phenytoin on glutathione status and oxidative stress biomarker gene mRNA levels in cultured precision human liver slices.
2001 Jan
The activity of NF-kappaB in Swiss 3T3 cells exposed to aqueous extracts of cigarette smoke is dependent on thioredoxin.
2001 Jan
Ochratoxin A-induced tumor formation: is there a role of reactive ochratoxin A metabolites?
2001 Jan
Dual effects of nitric oxide in functional and regressing rat corpus luteum.
2001 Jan
Effects of dietary supplementation of alpha-lipoic acid on early glomerular injury in diabetes mellitus.
2001 Jan
Major changes in human ocular UV protection with age.
2001 Jan
Dose response of carboplatin-induced hearing loss in rats: antioxidant defense system.
2001 Jan
Oxidative stress and antioxidant defenses in goldfish Carassius auratus during anoxia and reoxygenation.
2001 Jan
Overcoming drug resistance in ovarian carcinoma.
2001 Jan
Antioxidant modulation in response to metal-induced oxidative stress in algal chloroplasts.
2001 Jan
The effect of mercury and PCBs on organisms from lower trophic levels of a Georgia salt marsh.
2001 Jan
Homocysteine and thiol metabolites in vitamin B12 deficiency.
2001 Jan
Genomic organization and putative promoters of highly conserved glutathione S-transferases originating by alternative splicing in Anopheles dirus.
2001 Jan
Single amino acid changes outside the active site significantly affect activity of glutathione S-transferases.
2001 Jan
The intracellular oxidation of 2',7'-dichlorofluorescin in murine T lymphocytes.
2001 Jan 1
Thiols can either enhance or suppress DNA damage induction by catecholestrogens.
2001 Jan 1
Superoxide radical-initiated apoptotic signalling pathway in selenite-treated HepG(2) cells: mitochondria serve as the main target.
2001 Jan 1
Differential effects of bcl-2 on cell death triggered under ATP-depleting conditions.
2001 Jan 1
Evidence for the presence of phospholipid hydroperoxide glutathione peroxidase in human platelets: implications for its involvement in the regulatory network of the 12-lipoxygenase pathway of arachidonic acid metabolism.
2001 Jan 1
Tamoxifen mutagenesis and carcinogenesis in livers of lambda/lacI transgenic rats: selective influence of phenobarbital promotion.
2001 Jan 10
Catalase in astroglia-rich primary cultures from rat brain: immunocytochemical localization and inactivation during the disposal of hydrogen peroxide.
2001 Jan 12
Preventive effect of diethyldithiocarbamate on selenite-induced opacity in cultured rat lenses.
2001 Jan-Feb
Role of multidrug resistance protein 1 (MRP1) and glutathione S-transferase A1-1 in alkylating agent resistance. Kinetics of glutathione conjugate formation and efflux govern differential cellular sensitivity to chlorambucil versus melphalan toxicity.
2001 Mar 16
Characterization of transsulfuration and cysteine biosynthetic pathways in the protozoan hemoflagellate, Trypanosoma cruzi. Isolation and molecular characterization of cystathionine beta-synthase and serine acetyltransferase from Trypanosoma.
2001 Mar 2
WD repeat domains target dictyostelium myosin heavy chain kinases by binding directly to myosin filaments.
2001 Mar 2
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.
2001 Mar 2
The cytosolic O-acetylserine(thiol)lyase gene is regulated by heavy metals and can function in cadmium tolerance.
2001 Mar 23
gamma -glutamyltransferase and its isoform mediate an endoplasmic reticulum stress response.
2001 Mar 23
Enhanced multispecificity of arabidopsis vacuolar multidrug resistance-associated protein-type ATP-binding cassette transporter, AtMRP2.
2001 Mar 23
A conserved docking site in MEKs mediates high-affinity binding to MAP kinases and cooperates with a scaffold protein to enhance signal transmission.
2001 Mar 30
Structural properties and mechanisms that govern association of C kinase adapter 1 with protein kinase C3 and the cell periphery.
2001 Mar 30
Silencing mediator for retinoid and thyroid hormone receptors interacts with octamer transcription factor-1 and acts as a transcriptional repressor.
2001 Mar 30
Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite.
2001 Mar 30
CyaG, a novel cyanobacterial adenylyl cyclase and a possible ancestor of mammalian guanylyl cyclases.
2001 Mar 30
Functional characterization of and cooperation between the double-stranded RNA-binding motifs of the protein kinase PKR.
2001 Mar 30
A direct inhibitory role for the Rab3-specific effector, Noc2, in Ca2+-regulated exocytosis in neuroendocrine cells.
2001 Mar 30
Epilysin, a novel human matrix metalloproteinase (MMP-28) expressed in testis and keratinocytes and in response to injury.
2001 Mar 30
Phosphorylation of tau is regulated by PKN.
2001 Mar 30
Assembly of scaffold-mediated complexes containing Cdc42p, the exchange factor Cdc24p, and the effector Cla4p required for cell cycle-regulated phosphorylation of Cdc24p.
2001 Mar 9
Hrs interacts with sorting nexin 1 and regulates degradation of epidermal growth factor receptor.
2001 Mar 9
Interaction with p53 enhances binding of cisplatin-modified DNA by high mobility group 1 protein.
2001 Mar 9
The modulation of oxygen radical production by nitric oxide in mitochondria.
2001 Mar 9
Hierarchy of merlin and ezrin N- and C-terminal domain interactions in homo- and heterotypic associations and their relationship to binding of scaffolding proteins EBP50 and E3KARP.
2001 Mar 9
Protein kinase C activation modulates alpha-calmodulin kinase II binding to NR2A subunit of N-methyl-D-aspartate receptor complex.
2001 Mar 9
Patents

Sample Use Guides

For temporary relief of symptoms related to Free Radical Toxicity: 1-10 drops under the tongue, 3 times a day or as directed by a health professional. Consult a physician for use in children under 12 years of age. pain in the back from urinating: 10 drops orally, 3 times a day. Consult a physician for use in children under 12 years of age. Breast Cancer: RayGel Topical Cream applied in thin layer to the area exposed to radiation 60-90 minutes prior to radiotherapy, standard skin care between treatments. Cystic Fibrosis: Inhaled Reduced Glutathione 10 mg/kg, twice daily, 12 months
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
GLUTATHIONE
EP   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
GLUTATHIONE [VANDF]
Common Name English
GLUTATHIONE [INCI]
Common Name English
ISETHION
Common Name English
AEC GLUTATHIONE
Brand Name English
GLUTHAM
Brand Name English
REDUCED L-GLUTATHIONE
Common Name English
GLUTATHIONE [MI]
Common Name English
GLUTATHIONE [WHO-DD]
Common Name English
GLUTATHIONE [EP MONOGRAPH]
Common Name English
GLUTATHIONE [II]
Common Name English
GLUTATHIONE [MART.]
Common Name English
N-(N-L-.GAMMA.-GLUTAMYL-L-CYSTEINYL)GLYCINE
Systematic Name English
TATHIONE
Common Name English
GLYCINE, L-.GAMMA.-GLUTAMYL-L-CYSTEINYL-
Systematic Name English
GLUTATHIONE [USP-RS]
Common Name English
L-GLUTATHIONE REDUCED
Brand Name English
Classification Tree Code System Code
LOINC 57005-1
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
FDA ORPHAN DRUG 303410
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
LOINC 91685-8
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
DSLD 1621 (Number of products:627)
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
WHO-VATC QV03AB32
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
FDA ORPHAN DRUG 77493
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
LOINC 16918-5
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
LOINC 65363-4
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
FDA ORPHAN DRUG 545816
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
NCI_THESAURUS C275
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
FDA ORPHAN DRUG 311910
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
CFR 21 CFR 862.1365
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
FDA ORPHAN DRUG 519216
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
EU-Orphan Drug EU/3/06/361
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
DSLD 178 (Number of products:20)
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
WHO-ATC V03AB32
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
LOINC 2383-8
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
Code System Code Type Description
WIKIPEDIA
GLUTATHIONE
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
CAS
70-18-8
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
NCI_THESAURUS
C523
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL1543
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
DRUG BANK
DB00143
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
EVMPD
SUB13990MIG
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
RXCUI
4890
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY RxNorm
PUBCHEM
124886
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
EPA CompTox
70-18-8
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
DRUG CENTRAL
1312
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
MERCK INDEX
M5781
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-725-4
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
FDA UNII
GAN16C9B8O
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
MESH
D005978
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY
USP_CATALOG
1294820
Created by admin on Fri Jun 25 21:15:01 UTC 2021 , Edited by admin on Fri Jun 25 21:15:01 UTC 2021
PRIMARY USP-RS