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    Chemistry

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    Also known as: 70-18-8, L-glutathione, Glutathion, Isethion, L-glutathione reduced, Tathion
    Molecular Formula
    C10H17N3O6S
    Molecular Weight
    307.33  g/mol
    InChI Key
    RWSXRVCMGQZWBV-WDSKDSINSA-N
    FDA UNII
    GAN16C9B8O
    Glutathione
    A tripeptide with many roles in cells. 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.
    1 2D Structure

    Glutathione

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
    2.1.2 InChI
    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
    2.1.3 InChI Key
    RWSXRVCMGQZWBV-WDSKDSINSA-N
    2.1.4 Canonical SMILES
    C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N
    2.1.5 Isomeric SMILES
    C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    GAN16C9B8O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gamma L Glu L Cys Gly

    2. Gamma L Glutamyl L Cysteinylglycine

    3. Gamma-l-glu-l-cys-gly

    4. Gamma-l-glutamyl-l-cysteinylglycine

    5. Glutathione, Reduced

    6. Reduced Glutathione

    2.3.2 Depositor-Supplied Synonyms

    1. 70-18-8

    2. L-glutathione

    3. Glutathion

    4. Isethion

    5. L-glutathione Reduced

    6. Tathion

    7. Reduced Glutathione

    8. Glutathione-sh

    9. Glutinal

    10. Tathione

    11. Deltathione

    12. Neuthion

    13. Copren

    14. Glutide

    15. Triptide

    16. Ledac

    17. Gsh

    18. Glutatione

    19. Glutatiol

    20. Glutathione Reduced

    21. Panaron

    22. Glutathione Sh

    23. L-glutatione

    24. Agifutol S

    25. Glutathione (reduced)

    26. L-gamma-glutamyl-l-cysteinylglycine

    27. Gamma-l-glutamyl-l-cysteinylglycine

    28. Glutathione [jan]

    29. L-glutathione, Reduced

    30. Gamma-l-glutamyl-l-cysteinyl-glycine

    31. 5-l-glutamyl-l-cysteinylglycine

    32. Glutham

    33. Gamma-l-glutamylcysteinylglycine

    34. Glutathione Red

    35. Aec Glutathione

    36. Red. Glutathione

    37. Bakezyme Rx

    38. L-glutathione Reduce

    39. Glycine, L-gamma-glutamyl-l-cysteinyl-

    40. Reduced L-glutathione

    41. (2s)-2-amino-5-[[(2r)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic Acid

    42. (s)-2-amino-5-(((r)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)amino)-5-oxopentanoic Acid

    43. N-(n-gamma-l-glutamyl-l-cysteinyl)glycine

    44. N-(n-l-gamma-glutamyl-l-cysteinyl)glycine

    45. Glycine, N-(n-l-gamma-glutamyl-l-cysteinyl)-

    46. Gan16c9b8o

    47. L-glutamyl-l-cysteinylglycine

    48. L-glutathione (reduced Form)

    49. Glycine, L-.gamma.-glutamyl-l-cysteinyl-

    50. Benzenamine, 2-[(4-methoxyphenyl)methoxy]-

    51. Chebi:16856

    52. (2s)-2-amino-4-{[(1r)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic Acid

    53. 106272-20-2

    54. 95687-20-0

    55. Dsstox_cid_3101

    56. N-(n-l-.gamma.-glutamyl-l-cysteinyl)glycine

    57. N5-((r)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)-l-glutamine

    58. Dsstox_rid_76875

    59. Dsstox_gsid_23101

    60. [glu(-cys)]n-gly

    61. Mfcd00065939

    62. Cas-70-18-8

    63. (s)-2-amino-5-((r)-1-(carboxymethylamino)-3-mercapto-1-oxopropan-2-ylamino)-5-oxopentanoic Acid

    64. Glutathione, Reduced

    65. Ccris 2094

    66. Sr-05000002567

    67. Glutathione [ban:jan]

    68. Einecs 200-725-4

    69. L-glutathione Reduced Form

    70. Unii-gan16c9b8o

    71. Nsc 400639

    72. Phytochelatins

    73. Readisorb

    74. Glutathione;

    75. Nsc400639

    76. 1lbk

    77. Ncgc00094976-01

    78. Tathion (tn)

    79. Glutathione (jp17)

    80. Spectrum_000419

    81. 1oe7

    82. 1oe8

    83. 1r4w

    84. C(n-.gamma.glu-)g

    85. Glutathione [ii]

    86. Glutathione [mi]

    87. Reduced Glutathione,(s)

    88. Spectrum2_001500

    89. Spectrum3_000946

    90. Spectrum4_001056

    91. Spectrum5_000940

    92. Glutathione, Reduced Form

    93. Glutathione [inci]

    94. Bmse000185

    95. Bmse000952

    96. Bmse000956

    97. Glutathione (reduced Type)

    98. Glutathione [vandf]

    99. Cys(n-.gamma.glu-)-gly

    100. Schembl9167

    101. Chembl1543

    102. Glutathione [mart.]

    103. Glutathione [usp-rs]

    104. Glutathione [who-dd]

    105. Kbiogr_001352

    106. Kbioss_000899

    107. Mls001333069

    108. Divk1c_000075

    109. Spectrum1502248

    110. Spbio_001519

    111. Gamma-glutamyl-cysteinyl-glycine

    112. Gtpl6737

    113. Dtxsid6023101

    114. L-?-glutamyl-l-cysteinylglycine

    115. L-glutathione Reduced, 97.0%

    116. Chebi:60836

    117. Hms500d17

    118. Kbio1_000075

    119. Kbio2_000899

    120. Kbio2_003467

    121. Kbio2_006035

    122. Kbio3_002012

    123. (gamma-glutamylcysteine)n-glycine

    124. L-g-glutamyl-l-cysteinyl-glycine

    125. Y-l-glutamyl-l-cysteinyl-glycine

    126. L-?-glutamyl-l-cysteinyl-glycine

    127. Ninds_000075

    128. Glutathione [ep Monograph]

    129. Hms1921n22

    130. Pharmakon1600-01502248

    131. Poly(gamma-glutamylcysteine)glycine

    132. Hy-d0187

    133. L-glutathione Reduced, >=98.0%

    134. Zinc3830891

    135. Gam.-l-glutamyl-l-cysteinyl-glycine

    136. Tox21_111371

    137. Bdbm50422268

    138. Ccg-38876

    139. L-gamma-glutamyl-l-cysteinyl-glycine

    140. Nsc758199

    141. S4606

    142. Akos015999135

    143. Tox21_111371_1

    144. Cs-7948

    145. Db00143

    146. Nsc-758199

    147. Sdccgmls-0066687.p001

    148. .gamma.-l-glutamyl-l-cysteinyl-glycine

    149. Idi1_000075

    150. N-(n-l-?-glutamyl-l-cysteinyl)glycine

    151. Pharm Biol 11: 539 (1968)

    152. Smp1_000247

    153. Ncgc00264046-02

    154. Ds-14675

    155. Gsh;gamma-l-glutamyl-l-cysteinyl-glycine

    156. Smr000857220

    157. Sbi-0051743.p002

    158. L-glutathione Reduced, Bioxtra, >=98.0%

    159. B7775

    160. G0074

    161. Glycine, N-(n-l-gamma-glutamyl-l-cysteinyl)

    162. C00051

    163. C02471

    164. D00014

    165. G-3980

    166. P19615

    167. Ab00443568_03

    168. Glutathione 100 Microg/ml In Acetonitrile:water

    169. A866658

    170. Q116907

    171. Sr-05000002567-1

    172. Sr-05000002567-2

    173. L-glutathione Reduced, Vetec(tm) Reagent Grade, >=98%

    174. Z2183947556

    175. Glutathione, European Pharmacopoeia (ep) Reference Standard

    176. Glutathione, United States Pharmacopeia (usp) Reference Standard

    177. Glutathione, Pharmaceutical Secondary Standard; Certified Reference Material

    178. L-glutathione Reduced, Cell Culture Tested, Bioreagent, >=98.0%, Powder

    179. (2s)-2-amino-4-{[(1r)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoylbutanoic Acid

    180. (2s)-2-amino-5-({(2r)-1-[(carboxymethyl)amino]-1-oxo-3-sulfanyl-2-propanyl}amino)-5-oxopentanoic Acid

    181. Glutathione; L-glutathione Reduced; 5-l-glutamyl-l-cysteinylglycine; Gamma-l-glutamyl-l-cysteinylglycine; Gsh

    2.4 Create Date
    2005-06-08
    3 Chemical and Physical Properties
    Molecular Weight 307.33 g/mol
    Molecular Formula C10H17N3O6S
    XLogP3-4.5
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count9
    Exact Mass307.08380644 g/mol
    Monoisotopic Mass307.08380644 g/mol
    Topological Polar Surface Area160 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity389
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For nutritional supplementation, also for treating dietary shortage or imbalance

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    V - Various

    V03 - All other therapeutic products

    V03A - All other therapeutic products

    V03AB - Antidotes

    V03AB32 - Glutathione

    5.2 Absorption, Distribution and Excretion

    Absorption

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

    5.3 Mechanism of Action

    Glutathione (GSH) participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It also plays a role in the hepatic biotransformation and detoxification process; it acts as a hydrophilic molecule that is added to other lipophilic toxins or wastes prior to entering biliary excretion. It participates in the detoxification of methylglyoxal, a toxic by-product of metabolism, mediated by glyoxalase enzymes. 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. 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 a cofactor of conjugation and reduction reactions that are catalyzed by glutathione S-transferase enzymes expressed in the 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.

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INGREDIENTS","customerCountry":"INDIA","quantity":"650.00","actualQuantity":"650","unit":"KGS","unitRateFc":"53","totalValueFC":"36853.4","currency":"USD","unitRateINR":"4708.3","date":"14-Aug-2024","totalValueINR":"3060401.83","totalValueInUsd":"36853.4","indian_port":"Bombay Air","hs_no":"29309099","bill_no":"5047968","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Non Pharma","supplierPort":"EZHOU HUAHU","supplierAddress":"NO. 5 WEIYI ROAD, HIGH-TECH ZONE,ANQING CITY, ANHUI PROVINCE,SDNF CHINA","customerAddress":"N\/A"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724005800,"product":"G4251-VAR GLUTATHIONE FREE ACID REDUCED FORM*CRYST (FOR LABPURPOSE) (3500 GMS)","address":"PLOT.NO.12,BOMMASANDRA-JIGANI LINK","city":"BANGALORE","supplier":"MERCK GROUP","supplierCountry":"UNITED STATES","foreign_port":"CHICAGO, IL","customer":"SIGMA ALDRICH CHEMICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"3.50","actualQuantity":"3.5","unit":"KGS","unitRateFc":"182947.2","totalValueFC":"7715.3","currency":"INR","unitRateINR":"183057","date":"19-Aug-2024","totalValueINR":"640699.39","totalValueInUsd":"7715.3","indian_port":"Bangalore Air","hs_no":"29309070","bill_no":"5131580","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"CHICAGO, IL","supplierAddress":"2425 S 2ND ST ST LOUIS MO 63104-4712 United States, , United StatesSDNF United States","customerAddress":"PLOT.NO.12,BOMMASANDRA-JIGANI LINK"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724869800,"product":"L-GLUTATHIONE REDUCED ( NOT FOR MEDICINAL USE) CAS NO 70-18-8","address":"OFFICE NO 501, 5TH FLOOR, K L ACCOLADE, ROAD NO 6","city":"Mumbai","supplier":"HUNAN BIO-ESSENTIAL TECH CO.LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"CHEMKART INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"52","totalValueFC":"53263.8","currency":"USD","unitRateINR":"4423.2","date":"29-Aug-2024","totalValueINR":"4423172.92","totalValueInUsd":"53263.8","indian_port":"JNPT","hs_no":"29309099","bill_no":"5319063","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Non Pharma","supplierPort":"SHANGHAI","supplierAddress":"NO.317,KANGNING ROAD, LIUYANG NATIONAL ECONOMIC& TECHNICAL DEVELOPMENTZONE, CHINA CHINA","customerAddress":"OFFICE NO 501, 5TH FLOOR, K L ACCOLADE, ROAD NO 6"}]
    25-Jan-2021
    31-Aug-2024
    KGS
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