ContaminantDB: Glutathione

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (44)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:32:13 UTC

Update Date

2026-05-14 16:24:15 UTC

Accession Number

CHEM003312

Identification

Common Name

Glutathione

Class

Small Molecule

Description

Glutathione is a compound synthesized from cysteine, perhaps the most important member of the body's toxic waste disposal team. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells don't contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. Glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione (especially in the liver) binds with toxic chemicals in order to detoxify them. Glutathione is also important in red and white blood cell formation and throughout the immune system. glutathione's clinical uses include the prevention of oxygen toxicity in hyperbaric oxygen therapy, treatment of lead and other heavy metal poisoning, lowering of the toxicity of chemotherapy and radiation in cancer treatments, and reversal of cataracts. Glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. Glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is also capable of participating in non-enzymatic conjugation with some chemicals, as in the case of n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450-reactive metabolite formed by acetaminophen, that becomes toxic when GSH is depleted by an overdose (of acetaminophen). Glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein thiol groups which would otherwise be covalently modified; when all GSH has been spent, NAPQI begins to react with the cellular proteins, killing the cells in the process. The preferred treatment for an overdose of this painkiller is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and renew the usable GSH pool. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides.

Contaminant Sources

Cosmetic Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Animal Toxin
Dietary Supplement
Drug
Food Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-L-Glutamyl-L-cysteinylglycine	ChEBI
gamma-L-Glutamyl-L-cysteinyl-glycine	ChEBI
Glutathione-SH	ChEBI
GSH	ChEBI
N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine	ChEBI
Reduced glutathione	ChEBI
Poly(gamma-glutamylcysteine)glycine	Kegg
(gamma-Glutamylcysteine)N-glycine	Kegg
Tathion	Kegg
g-L-Glutamyl-L-cysteinyl-glycine	Generator
Γ-L-glutamyl-L-cysteinyl-glycine	Generator
N-(N-g-L-Glutamyl-L-cysteinyl)glycine	Generator
N-(N-Γ-L-glutamyl-L-cysteinyl)glycine	Generator
Poly(g-glutamylcysteine)glycine	Generator
Poly(γ-glutamylcysteine)glycine	Generator
(g-Glutamylcysteine)N-glycine	Generator
(Γ-glutamylcysteine)N-glycine	Generator
Agifutol S	HMDB
Bakezyme RX	HMDB
Copren	HMDB
Deltathione	HMDB
gamma-Glutamylcysteinylglycine	HMDB
gamma-L-Glutamyl-L-cysteinylglycine	HMDB
Glutathion	HMDB
Glutathione red	HMDB
Glutathione reduced	HMDB
Glutatiol	HMDB
Glutatione	HMDB
Glutide	HMDB
Glutinal	HMDB
Isethion	HMDB
L-g-Glutamyl-L-cysteinyl-glycine	HMDB
L-gamma-Glutamyl-L-cysteinyl-glycine	HMDB
L-gamma-Glutamyl-L-cysteinylglycine	HMDB
L-Glutamyl-L-cysteinylglycine	HMDB
L-Glutathione	HMDB
L-Glutathione reduce	HMDB
Ledac	HMDB
Neuthion	HMDB
Red. glutathione	HMDB
Tathione	HMDB
Triptide	HMDB
Glutathione, reduced	HMDB
gamma L Glu L cys gly	HMDB
gamma-L-Glu-L-cys-gly	HMDB
gamma L Glutamyl L cysteinylglycine	HMDB

Chemical Formula

C₁₀H₁₇N₃O₆S

Average Molecular Mass

307.323 g/mol

Monoisotopic Mass

307.084 g/mol

CAS Registry Number

70-18-8

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid

Traditional Name

glutathione

SMILES

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

InChI Identifier

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

InChI Key

RWSXRVCMGQZWBV-WDSKDSINSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as peptides. Peptides 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

Substituents

Alpha peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Amino acid or derivatives
Amino acid
Alkylthiol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

thiol (CHEBI:16856 )
L-cysteine derivative (CHEBI:16856 )
tripeptide (CHEBI:16856 )
Coenzymes (C00051 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

All Tissues

Pathways

Name	SMPDB Link	KEGG Link
Arachidonic Acid Metabolism	SMP00075	map00590
Glutamate Metabolism	SMP00072	map00250
Glutathione Metabolism	SMP00015	map00480
Pyruvaldehyde Degradation	SMP00459	Not Available
Gamma-Glutamyltransferase Deficiency	SMP00183	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

antioxidant

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	195°C
Boiling Point	Not Available
Solubility	292.5 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-4.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	69.11 m³·mol⁻¹	ChemAxon
Polarizability	29.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-0a4i-0900000000-5841845f736f9a667622	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-0a4i-0900000000-bdecde153761cb67852e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-5841845f736f9a667622	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-bdecde153761cb67852e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-1910000000-52bc43dd913b68d74f84	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-08fs-3960000000-63ce34def2ae94b95515	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0pb9-0921000000-88168b0a9f5fc5fead3f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7890000000-5853006f66d946dd3d2e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0596-9112300000-e82cf72540c283d8e323	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-3795000000-d019cd7dcbad1f8a9e78	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-003r-9400000000-a83bf6292d41988256e3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-305a92f8a9ffea58fa0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009000000-e950bfc5867b391c6960	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0910000000-83f6c079d1112e74ecf4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-003r-0910000000-5b243cf8bd357ab270b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009000000-29ef335479f56b620d88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009001000-d1f5986166efa523d024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-056s-0495300000-dba7be381fd1ef776527	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0920000000-de5b8a5a377324599b39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-053r-0007920000-7500cef211e48c8ea244	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0119003000-4eb7ed4e2a4cf6a83c66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0uki-0290000000-6893386899c6eed6a1a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-05g0-0190000000-cacc2de4ab18ed59798b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0009000000-6b4268add43ab66ef015	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-08fr-0015009000-a01bdc13a34d6ce8416f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0uki-0290000000-ea94ec8247b4e025adbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0039210000-e1f721157a9ea89959d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a59-0039210000-35ce450ea95922abf0e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0009000000-9b01fba547d1fcde113a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0952000000-4a2a42699cf4aab2c559	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-002f-2900000000-bd9ba27b48b1322b7618	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004m-5900000000-cc7184d5bba50e6e49d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9200000000-aecd0eb18a10c3ffb7ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0729-4492000000-78a928563adf9038ba59	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Research suggests that glutathione is not orally bioactive, and that very little of oral glutathione tablets or capsules is actually absorbed by the body.

Mechanism of Toxicity

Glutathione (GSH) participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. Glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II catalyzes the conversion of S-D-Lactoyl Glutathione to Reduced Glutathione and D-lactate. GSH is known as a cofactor in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is capable of participating in non-enzymatic conjugation with some chemicals, as it is hypothesized to do to a significant extent with n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450 reactive metabolite formed by toxic overdose of acetaminophen. Glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein sulfhydryl groups which would otherwise be toxically adducted. The preferred medical treatment to an overdose of this nature, whose efficacy has been consistently supported in literature, is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and allow a usable GSH pool.

Metabolism

Not Available

Toxicity Values

ORL-MUS LD₅₀ 5000 mg/kg, IPR-MUS LD₅₀ 4020 mg/kg, SCU-MUS LD₅₀ 5000 mg/kg, IVN-RBT LD₅₀ > 2000 mg/kg, IMS-MUS LD₅₀ 4000 mg/kg

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For nutritional supplementation, also for treating dietary shortage or imbalance

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00143

HMDB ID

HMDB0000125

FooDB ID

FDB001498

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001518

BiGG ID

33669

BioCyc ID

GLUTATHIONE

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Akihiro Mizutani, “Complexes of polysaccharides or derivatives thereof with reduced glutathione and process for preparing said complexes.” U.S. Patent US4009264, issued February, 1971.

MSDS

Link

General References

1. Djurhuus R, Segadal K, Svardal AM: Glutathione in blood cells decreases without DNA breaks after a simulated saturation dive to 250 msw. Aviat Space Environ Med. 2006 Jun;77(6):597-604.

2. Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8.

3. Hung CR: Effect of lysozyme chloride on betel quid chewing aggravated gastric oxidative stress and hemorrhagic ulcer in diabetic rats. World J Gastroenterol. 2005 Oct 7;11(37):5853-8.

4. Grattagliano I, Portincasa P, Palmieri VO, Palasciano G: Contribution of canalicular glutathione efflux to bile formation. From cholestasis associated alterations to pharmacological intervention to modify bile flow. Curr Drug Targets Immune Endocr Metabol Disord. 2005 Jun;5(2):153-61.

5. Calvo-Marzal P, Chumbimuni-Torres KY, Hoehr NF, Kubota LT: Determination of glutathione in hemolysed erythrocyte with amperometric sensor based on TTF-TCNQ. Clin Chim Acta. 2006 Sep;371(1-2):152-8. Epub 2006 May 2.

6. Calabrese V, Scapagnini G, Ravagna A, Bella R, Butterfield DA, Calvani M, Pennisi G, Giuffrida Stella AM: Disruption of thiol homeostasis and nitrosative stress in the cerebrospinal fluid of patients with active multiple sclerosis: evidence for a protective role of acetylcarnitine. Neurochem Res. 2003 Sep;28(9):1321-8.

7. Sohlenius-Sternbeck AK, Schmidt S: Impaired glutathione-conjugating capacity by cryopreserved human and rat hepatocytes. Xenobiotica. 2005 Jul;35(7):727-36.

8. Iida M, Yasuhara T, Mochizuki H, Takakura H, Yanagisawa T, Kubo H: Two Japanese brothers with hereditary gamma-glutamyl transpeptidase deficiency. J Inherit Metab Dis. 2005;28(1):49-55.

9. Briz O, Romero MR, Martinez-Becerra P, Macias RI, Perez MJ, Jimenez F, San Martin FG, Marin JJ: OATP8/1B3-mediated cotransport of bile acids and glutathione: an export pathway for organic anions from hepatocytes? J Biol Chem. 2006 Oct 13;281(41):30326-35. Epub 2006 Jul 28.