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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H17N3O6S
Molecular Weight 307.323
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Glutathione

SMILES

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

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)
Conditions
PubMed

PubMed

TitleDatePubMed
Differential catalytic efficiency of allelic variants of human glutathione S-transferase Pi in catalyzing the glutathione conjugation of thiotepa.
1999 Jun 1
Elevation of glutathione level in rat hepatocytes by hepatocyte growth factor via induction of gamma-glutamylcysteine synthetase.
1999 Nov
Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones.
1999 Oct 1
Novel biphasic effect of pyrrolidine dithiocarbamate on neuronal cell viability is mediated by the differential regulation of intracellular zinc and copper ion levels, NF-kappaB, and MAP kinases.
2000 Jan 1
The catalytic Tyr-9 of glutathione S-transferase A1-1 controls the dynamics of the C terminus.
2000 Jun 9
Reactive oxygen species and proinflammatory cytokine signaling in endothelial cells: effect of selenium supplementation.
2000 Mar 15
Simultaneous inhibition of renal phospholipase A(2) and glutathione synthesis by manoalide and DL-buthionine sulfoximine induces acute tubular dysfunction in rats.
2000 Mar-Apr
Localization of the C-terminus of rat glutathione S-transferase A1-1: crystal structure of mutants W21F and W21F/F220Y.
2001 Feb 1
Nitrogen monoxide (no) and glucose: unexpected links between energy metabolism and no-mediated iron mobilization from cells.
2001 Feb 16
The glutathione transferase structural family includes a nuclear chloride channel and a ryanodine receptor calcium release channel modulator.
2001 Feb 2
The kinetic mechanism of the dual phosphorylation of the ATF2 transcription factor by p38 mitogen-activated protein (MAP) kinase alpha. Implications for signal/response profiles of MAP kinase pathways.
2001 Feb 23
Human glutathione transferase T2-2 discloses some evolutionary strategies for optimization of the catalytic activity of glutathione transferases.
2001 Feb 23
Cloning, expression, and up-regulation of inducible rat prostaglandin e synthase during lipopolysaccharide-induced pyresis and adjuvant-induced arthritis.
2001 Feb 9
Effects of phenytoin on glutathione status and oxidative stress biomarker gene mRNA levels in cultured precision human liver slices.
2001 Jan
Ochratoxin A-induced tumor formation: is there a role of reactive ochratoxin A metabolites?
2001 Jan
Effects of dietary supplementation of alpha-lipoic acid on early glomerular injury in diabetes mellitus.
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
Cellular thiols and reactive oxygen species in drug-induced apoptosis.
2001 Jan
Glutathione in disease.
2001 Jan
Greater susceptibility of failing cardiac myocytes to oxygen free radical-mediated injury.
2001 Jan
The effect of mercury and PCBs on organisms from lower trophic levels of a Georgia salt marsh.
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
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
Synergistic enhancement of nuclear receptor function by p160 coactivators and two coactivators with protein methyltransferase activities.
2001 Jan 12
Association with the nuclear matrix and interaction with Groucho and RUNX proteins regulate the transcription repression activity of the basic helix loop helix factor Hes1.
2001 Jan 12
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
A proteome analysis of the cadmium response in Saccharomyces cerevisiae.
2001 Mar 16
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
Silencing mediator for retinoid and thyroid hormone receptors interacts with octamer transcription factor-1 and acts as a transcriptional repressor.
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
Hrs interacts with sorting nexin 1 and regulates degradation of epidermal growth factor receptor.
2001 Mar 9
A genetic investigation of the essential role of glutathione: mutations in the proline biosynthesis pathway are the only suppressors of glutathione auxotrophy in yeast.
2001 Mar 9
Expression-independent consumption of substrates in cell-free expression system from Escherichia coli.
2001 Nov 17
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
γ-Glutamylcysteinylglycine
Systematic Name English
GLUTATHIONE [INCI]
Common Name English
ISETHION
Common Name English
γ-Glu-Cys-Gly
Systematic Name English
GLUTATHIONE, L-
Common Name English
GLUTATHIONE [JAN]
Common Name English
GLUTHAM
Brand Name English
REDUCED L-GLUTATHIONE
Common Name English
GLUTATHIONE [MI]
Common Name English
GLUTATHIONE [EP MONOGRAPH]
Common Name English
GLUTATHIONE [II]
Common Name English
GLUTATHIONE [MART.]
Common Name English
L-γ-Glutamyl-L-cysteinylglycine
Systematic Name English
TATHIONE
Common Name English
Glutathione [WHO-DD]
Common Name English
Glycine, L-γ-glutamyl-L-cysteinyl-
Systematic Name English
NSC-400639
Code 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 Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
FDA ORPHAN DRUG 303410
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
LOINC 91685-8
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
DSLD 1621 (Number of products:627)
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
WHO-VATC QV03AB32
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
FDA ORPHAN DRUG 77493
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
LOINC 16918-5
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
LOINC 65363-4
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
FDA ORPHAN DRUG 545816
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
NCI_THESAURUS C275
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
FDA ORPHAN DRUG 311910
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
CFR 21 CFR 862.1365
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
FDA ORPHAN DRUG 519216
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
EU-Orphan Drug EU/3/06/361
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
DSLD 178 (Number of products:20)
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
WHO-ATC V03AB32
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
LOINC 2383-8
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1294820
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
DAILYMED
GAN16C9B8O
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
CHEBI
16856
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
WIKIPEDIA
GLUTATHIONE
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
NSC
400639
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
CHEBI
57925
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
SMS_ID
100000092913
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
CAS
70-18-8
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
NCI_THESAURUS
C523
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL1543
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
DRUG BANK
DB00143
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
EVMPD
SUB13990MIG
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
RXCUI
4890
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY RxNorm
PUBCHEM
124886
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID6023101
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
244
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
293
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
DRUG CENTRAL
1312
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
MERCK INDEX
m5781
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-725-4
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
FDA UNII
GAN16C9B8O
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY
MESH
D005978
Created by admin on Fri Dec 15 15:12:46 UTC 2023 , Edited by admin on Fri Dec 15 15:12:46 UTC 2023
PRIMARY