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Probucol

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ACTIVE PHARMA INGREDIENTS

7 API Suppliers, 5 USDMF, 3 JDMF, 1 NDC API, 1 Listed Suppliers

7 API Suppliers
5 USDMF
3 JDMF
1 NDC API
1 Listed Suppliers

FINISHED DOSAGE FORMULATIONS

2 FDF Dossiers, 2 FDA Orange Book

2 FDF Dossiers
2 FDA Orange Book

REF. STANDARDS & IMPURITIES

4 USP , 4 JP , 4 Others

otherSolutions
4 USP
4 JP
4 Others

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 0

MARKET PLACE

API

FDF

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

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Finished Drug Prices

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Chemistry

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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

Probucol

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 Formula	C₃₁H₄₈O₂S₂
Molecular Weight	516.8 g/mol
XLogP3	11.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	8
Exact Mass	516.30957312 g/mol
Monoisotopic Mass	516.30957312 g/mol
Topological Polar Surface Area	91.1 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	583
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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