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

Molecular Formula C10H17N3O6S
Molecular Weight 307.325
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Synergistic effect of diesel organic extracts and allergen Der p 1 on the release of chemokines by peripheral blood mononuclear cells from allergic subjects: involvement of the map kinase pathway.
2000 Aug
The protective effect of glutathione administration on adriamycin-induced acute cardiac toxicity in rats.
2000 Aug
Apoptosis induced by extracellular glutathione is mediated by H(2)O(2) production and DNA damage.
2000 Aug 1
A lens glutathione S-transferase, class mu, with thiol-specific antioxidant activity.
2000 Sep
Assays for mitogen-activated protein kinase (MAPK) subtypes and MAPK activating protein kinase-2 (MAPKAP K-2) using a common cell lysate.
2001
Direct interaction between endothelial nitric-oxide synthase and dynamin-2. Implications for nitric-oxide synthase function.
2001 Apr 27
Nitrogen monoxide (no) and glucose: unexpected links between energy metabolism and no-mediated iron mobilization from cells.
2001 Feb 16
Glutathiolation of proteins by glutathione disulfide S-oxide derived from S-nitrosoglutathione. Modifications of rat brain neurogranin/RC3 and neuromodulin/GAP-43.
2001 Feb 2
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 substrate binding to the active site of glutathione transferases.
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
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
Major changes in human ocular UV protection with age.
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
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
Synergistic enhancement of nuclear receptor function by p160 coactivators and two coactivators with protein methyltransferase activities.
2001 Jan 12
Affinity labeling of rat glutathione S-transferase isozyme 1-1 by 17beta -iodoacetoxy-estradiol-3-sulfate.
2001 Jan 19
2-acetylaminofluorene up-regulates rat mdr1b expression through generating reactive oxygen species that activate NF-kappa B pathway.
2001 Jan 5
Eosinophil peroxidase oxidation of thiocyanate. Characterization of major reaction products and a potential sulfhydryl-targeted cytotoxicity system.
2001 Jan 5
Inhibition of adenylate cyclase activity by 5-aminolevulinic acid in rat and human brain.
2001 Mar
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
Interaction of the type IIa Na/Pi cotransporter with PDZ proteins.
2001 Mar 23
Structural properties and mechanisms that govern association of C kinase adapter 1 with protein kinase C3 and the cell periphery.
2001 Mar 30
Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite.
2001 Mar 30
Phosphorylation of tau is regulated by PKN.
2001 Mar 30
Interaction with p53 enhances binding of cisplatin-modified DNA by high mobility group 1 protein.
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
Zinc release from the CH2C6 zinc finger domain of FILAMENTOUS FLOWER protein from Arabidopsis thaliana induces self-assembly.
2001 Mar 9
The putative glutathione peroxidase gene of Plasmodium falciparum codes for a thioredoxin peroxidase.
2001 Mar 9
Novel G proteins, Rag C and Rag D, interact with GTP-binding proteins, Rag A and Rag B.
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:15:01 UTC 2021
Edited
by admin
on Fri Jun 25 21:15:01 UTC 2021
Record UNII
GAN16C9B8O
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
SUBSTRATE -> TARGET
DERIVATIVE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY