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    Probucol

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 23288-49-5, Lorelco, Biphenabid, Bisphenabid, Lurselle, Bisbid
    Molecular Formula
    C31H48O2S2
    Molecular Weight
    516.8  g/mol
    InChI Key
    FYPMFJGVHOHGLL-UHFFFAOYSA-N
    FDA UNII
    P3CTH044XJ
    A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenol
    2.1.2 InChI
    InChI=1S/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3
    2.1.3 InChI Key
    FYPMFJGVHOHGLL-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)SC(C)(C)SC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    P3CTH044XJ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Biphenabid

    2. Dh 581

    3. Dh-581

    4. Dh581

    5. Lorelco

    6. Lurselle

    7. Panavir

    8. Superlipid

    2.3.2 Depositor-Supplied Synonyms

    1. 23288-49-5

    2. Lorelco

    3. Biphenabid

    4. Bisphenabid

    5. Lurselle

    6. Bisbid

    7. Lesterol

    8. Lursell

    9. Dh-581

    10. Panavir

    11. Probucolum

    12. Sinlestal

    13. Probucolum [inn-latin]

    14. Dh 581

    15. Acetone Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole

    16. 4,4'-(isopropylidenedithio)bis(2,6-di-tert-butylphenol)

    17. 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenol

    18. 4,4'-(propane-2,2-diylbis(sulfanediyl))bis(2,6-di-tert-butylphenol)

    19. Nsc 86225

    20. Nsc 652160

    21. Acetone, Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole

    22. 2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol

    23. Nsc-86225

    24. Chembl608

    25. Nsc-652160

    26. 4,4'-(propane-2,2-diyldisulfanediyl)bis(2,6-di-tert-butylphenol)

    27. P3cth044xj

    28. Mls000028492

    29. Chebi:8427

    30. Nsc86225

    31. Phenol, 4,4'-[(1-methylethylidene)bis(thio)]bis[2,6-bis(1,1-dimethylethyl)-

    32. Nsc652160

    33. 4,4'-(isopropylidenedithio)bis(2, 6-di-tert-butylphenol)

    34. 4,4'-(isopropylidenedithio)bis[2, 6-di-tert-butylphenol]

    35. Ncgc00016777-01

    36. Smr000058265

    37. Superlipid

    38. Cas-23288-49-5

    39. Phenol, 4,4'-((1-methylethylidene)bis(thio))bis(2,6-bis(1,1-dimethylethyl)-

    40. Dsstox_cid_25440

    41. Dsstox_rid_80881

    42. Dsstox_gsid_45440

    43. 4,4'- (isopropylidenedithio)bis(2,6-di-tert-butylphenol)

    44. Ccris 7510

    45. Dh581

    46. Sr-01000695447

    47. Lorelco (tn)

    48. Einecs 245-560-9

    49. Unii-p3cth044xj

    50. Brn 2026253

    51. Serterol

    52. Probucol,(s)

    53. Prestwick_408

    54. Mfcd00079281

    55. Probucol [usan:usp:inn:ban:jan]

    56. De-3872

    57. Spectrum_001296

    58. Acetone, Bis (3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole

    59. Probucol [usan]

    60. Probucol [inn]

    61. Probucol [jan]

    62. Probucol [mi]

    63. Probucol [vandf]

    64. Opera_id_1820

    65. Prestwick0_000384

    66. Prestwick1_000384

    67. Prestwick2_000384

    68. Prestwick3_000384

    69. Spectrum2_001400

    70. Spectrum3_001438

    71. Spectrum4_000414

    72. Spectrum5_001343

    73. Probucol [mart.]

    74. Probucol [usp-rs]

    75. Probucol [who-dd]

    76. Schembl4150

    77. Bspbio_000567

    78. Bspbio_003176

    79. Kbiogr_000708

    80. Kbiogr_002394

    81. Kbioss_001776

    82. Kbioss_002399

    83. Probucol, Analytical Standard

    84. Divk1c_000599

    85. Spectrum1501109

    86. Probucol (jp17/usp/inn)

    87. Spbio_001420

    88. Spbio_002488

    89. Probucol [orange Book]

    90. Bpbio1_000625

    91. Gtpl7277

    92. Probucol [usp Impurity]

    93. Dtxsid2045440

    94. Hms501n21

    95. Kbio1_000599

    96. Kbio2_001776

    97. Kbio2_002394

    98. Kbio2_004344

    99. Kbio2_004962

    100. Kbio2_006912

    101. Kbio2_007530

    102. Kbio3_002396

    103. Kbio3_002873

    104. Cmap_000039

    105. Ninds_000599

    106. 4,4'- (isopropylidenedithio)bis(2, 6-di-tert-butylphenol)

    107. Hms1569m09

    108. Hms1921d21

    109. Hms2092d05

    110. Hms2096m09

    111. Hms2233c08

    112. Hms3655p19

    113. Hms3713m09

    114. Pharmakon1600-01501109

    115. Bcp06487

    116. Hy-b0388

    117. Zinc1530755

    118. Tox21_110605

    119. Bdbm50007260

    120. Ccg-38986

    121. Nsc757837

    122. S2119

    123. Stk762566

    124. Akos001740866

    125. Tox21_110605_1

    126. Db01599

    127. Ks-1459

    128. Nsc-757837

    129. 2,6-bis(tert-butyl)-4-{1-[3,5-bis(tert-butyl)-4-hydroxyphenylthio]-isopropylth Io}phenol

    130. Idi1_000599

    131. Ncgc00016777-02

    132. Ncgc00016777-03

    133. Ncgc00016777-04

    134. Ncgc00016777-05

    135. Ncgc00016777-06

    136. Ncgc00016777-07

    137. Ncgc00016777-08

    138. Ncgc00094895-01

    139. Ncgc00094895-02

    140. Ncgc00094895-03

    141. Ncgc00094895-04

    142. Ac-31457

    143. Bp166196

    144. Sbi-0051640.p002

    145. Db-046120

    146. Ab00052202

    147. Ft-0630498

    148. P2002

    149. Sw196648-3

    150. C07373

    151. D00476

    152. F20384

    153. Ab00052202_14

    154. Ab00052202_15

    155. 288p495

    156. A918612

    157. Acetone,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole

    158. Sr-01000695447-2

    159. Sr-01000695447-3

    160. W-107409

    161. Brd-k72029282-001-04-8

    162. Brd-k72029282-001-15-4

    163. Q10354103

    164. Acetone Bis(3,5-di-t-butyl-4-hydroxyphenyl) Mercaptole

    165. Z1551900339

    166. Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone

    167. Probucol, United States Pharmacopeia (usp) Reference Standard

    168. Phenol,4'-[(1-methylethylidene)bis(thio)]bis[2,6-bis(1,1-dimethylethyl)-

    169. 2,6-di-tert-butyl-4-(2-(3,5-di-tert-butyl-4-hydroxyphenylthio)propan-2-ylthio)phenol

    170. 4,4'-[(1-methylethylidene)bis(thio)]bis[2,6-bis(1,1-dimethylethyl)phenol]

    171. 2,6-di(tert-butyl)-4-[(1-{[3,5-di(tert-butyl)-4-hydroxyphenyl]sulfanyl}-1-methylethyl)sulfanyl]phenol

    172. 2,6-di(tert-butyl)-4-{1-[3,5-di(tert-butyl)-4-hydroxyphenylsulfanyl]-1-methylethylsulfanyl}phenol

    173. 2,6-di(tert-butyl)-4-{1-[3,5-di(tert-butyl)-4-hydroxyphenylsulfanyl]-1-methylethylsulfanyl}phenol(probucol)

    174. 2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenol

    175. 2,6-ditert-butyl-4-((1-[(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl]-1-methylethyl)sulfanyl)phenol #

    176. 2,6-ditert-butyl-4-[1-(3,5-ditert-butyl-4-hydroxy-phenyl)sulfanyl-1-methyl-ethyl]sulfanyl-phenol

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 516.8 g/mol
    Molecular Formula C31H48O2S2
    XLogP311.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count8
    Exact Mass516.30957312 g/mol
    Monoisotopic Mass516.30957312 g/mol
    Topological Polar Surface Area91.1 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity583
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    Used to lower LDL and HDL cholesterol.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Probucol lowers cholesterol levels by increasing LDL (low-density lipoprotein) breakdown. Additionally, probucol may inhibit cholesterol synthesis and delay cholesterol absorption. Probucol is a powerful antioxidant drug normally used to prevent vascular disease caused by the free radicals in the body.

    5.2 MeSH Pharmacological Classification

    Anticholesteremic Agents

    Substances used to lower plasma cholesterol levels. (See all compounds classified as Anticholesteremic Agents.)

    Antioxidants

    Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

    5.3 ATC Code

    C - Cardiovascular system

    C10 - Lipid modifying agents

    C10A - Lipid modifying agents, plain

    C10AX - Other lipid modifying agents

    C10AX02 - Probucol

    5.4 Absorption, Distribution and Excretion

    Absorption

    Absorption from the gastrointestinal tract is limited and variable (about 7%).

    5.5 Biological Half-Life

    Ranges from 12 hours to more than 500 hours, the longest half-life probably being in adipose tissue.

    5.6 Mechanism of Action

    Probucol lowers serum cholesterol by increasing the fractional rate of low-density lipoprotein (LDL) catabolism in the final metabolic pathway for cholesterol elimination from the body. This drug may also act to inhibit the initial stages of cholesterol synthesis and act to inhibit the absorption of cholesterol from the diet. Recent information suggests that probucol may inhibit the oxidation and tissue deposition of LDL cholesterol, thereby inhibiting atherogenesis. It appears to inhibits ABCA1-mediated cellular lipid efflux.