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 role of ethanol and acetaldehyde in the induction of oxidative stress in HEP G2 cells: effect on transcription factors AP-1 and NF-kappaB.
1999 Dec
CD95-Mediated murine hepatic apoptosis requires an intact glutathione status.
1999 Jul
Differential catalytic efficiency of allelic variants of human glutathione S-transferase Pi in catalyzing the glutathione conjugation of thiotepa.
1999 Jun 1
Determination of tetrahydrothiophene formation as a probe of in vitro busulfan metabolism by human glutathione S-transferase A1-1: use of a highly sensitive gas chromatographic-mass spectrometric method.
1999 Jun 25
Stimulation of p38 mitogen-activated protein kinase is an early regulatory event for the cadmium-induced apoptosis in human promonocytic cells.
2000 Apr 14
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
Mitochondrial adaptations to obesity-related oxidant stress.
2000 Jun 15
Ligand-induced changes in the structure and dynamics of a human class Mu glutathione S-transferase.
2000 Jun 27
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
A lens glutathione S-transferase, class mu, with thiol-specific antioxidant activity.
2000 Sep
Detection of phosphorylation-dependent interactions by far-western gel overlay.
2001
Assays for mitogen-activated protein kinase (MAPK) subtypes and MAPK activating protein kinase-2 (MAPKAP K-2) using a common cell lysate.
2001
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
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
Dual effects of nitric oxide in functional and regressing rat corpus luteum.
2001 Jan
Dose response of carboplatin-induced hearing loss in rats: antioxidant defense system.
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
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
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
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
Reconstitution of pterin-free inducible nitric-oxide synthase.
2001 Jan 5
Preventive effect of diethyldithiocarbamate on selenite-induced opacity in cultured rat lenses.
2001 Jan-Feb
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
The cytosolic O-acetylserine(thiol)lyase gene is regulated by heavy metals and can function in cadmium tolerance.
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
CyaG, a novel cyanobacterial adenylyl cyclase and a possible ancestor of mammalian guanylyl cyclases.
2001 Mar 30
A direct inhibitory role for the Rab3-specific effector, Noc2, in Ca2+-regulated exocytosis in neuroendocrine cells.
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
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
Zinc release from the CH2C6 zinc finger domain of FILAMENTOUS FLOWER protein from Arabidopsis thaliana induces self-assembly.
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
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 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
FDA ORPHAN DRUG 303410
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
LOINC 91685-8
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
DSLD 1621 (Number of products:627)
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
WHO-VATC QV03AB32
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
FDA ORPHAN DRUG 77493
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
LOINC 16918-5
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
LOINC 65363-4
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
FDA ORPHAN DRUG 545816
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
NCI_THESAURUS C275
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FDA ORPHAN DRUG 311910
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
CFR 21 CFR 862.1365
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
FDA ORPHAN DRUG 519216
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
EU-Orphan Drug EU/3/06/361
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
DSLD 178 (Number of products:20)
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
WHO-ATC V03AB32
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
LOINC 2383-8
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Code System Code Type Description
RS_ITEM_NUM
1294820
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
DAILYMED
GAN16C9B8O
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
CHEBI
16856
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
WIKIPEDIA
GLUTATHIONE
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
NSC
400639
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
CHEBI
57925
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
SMS_ID
100000092913
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
CAS
70-18-8
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
NCI_THESAURUS
C523
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL1543
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PRIMARY
DRUG BANK
DB00143
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
EVMPD
SUB13990MIG
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
RXCUI
4890
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY RxNorm
PUBCHEM
124886
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PRIMARY
EPA CompTox
DTXSID6023101
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PRIMARY
GRAS Notification (GRN No.)
244
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PRIMARY
GRAS Notification (GRN No.)
293
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
DRUG CENTRAL
1312
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PRIMARY
MERCK INDEX
m5781
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-725-4
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
FDA UNII
GAN16C9B8O
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY
MESH
D005978
Created by admin on Fri Dec 15 15:12:46 GMT 2023 , Edited by admin on Fri Dec 15 15:12:46 GMT 2023
PRIMARY