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(+/-)-1-(P,.ALPHA.-DIPHENYLBENZYL)IMIDAZOLE

(+/-)-1-(P,.ALPHA.-DIPHENYLBENZYL)IMIDAZOLE

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(+-)-1-(p,alpha-Diphenylbenzyl)imidazole

Also known as: 60628-96-8, Mycospor, Trifonazole, Bifonazol, Bay h 4502, Amycor

Molecular Formula

C₂₂H₁₈N₂

Molecular Weight

310.4 g/mol

InChI Key

OCAPBUJLXMYKEJ-UHFFFAOYSA-N

FDA UNII

QYJ305Z91O

Bifonazole is an azole antifungal drug.

1 2D Structure

(+-)-1-(p,alpha-Diphenylbenzyl)imidazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[phenyl-(4-phenylphenyl)methyl]imidazole

2.1.2 InChI

InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H

2.1.3 InChI Key

OCAPBUJLXMYKEJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C2=CC=C(C=C2)C(C3=CC=CC=C3)N4C=CN=C4

2.2 Other Identifiers

2.2.1 UNII

QYJ305Z91O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-((4-biphenylyl)-phenylmethyl)-1h-imidazole

2. Amycor

3. Bay H 4502

4. Bay H-4502

5. Bifokey

6. Bifomyk

7. Bifon

8. Moldina

9. Mycospor

2.3.2 Depositor-Supplied Synonyms

1. 60628-96-8

2. Mycospor

3. Trifonazole

4. Bifonazol

5. Bay H 4502

6. Amycor

7. Azolmen

8. Bifonazol [inn-spanish]

9. Bifonazolum [inn-latin]

10. 1-[phenyl-(4-phenylphenyl)methyl]imidazole

11. Bay H-4502

12. 1-((4-biphenylyl)phenylmethyl)-1h-imidazole

13. 1-(alpha-(4-biphenylyl)benzyl)imidazole

14. (+-)-1-(p,alpha-diphenylbenzyl)imidazole

15. Bay-h-4502

16. 1h-imidazole, 1-([1,1'-biphenyl]-4-ylphenylmethyl)-

17. 1-(p,alpha-diphenylbenzyl)imidazole

18. D01ac10

19. 1-([1,1'-biphenyl]-4-yl(phenyl)methyl)-1h-imidazole

20. Nsc-758954

21. Mls000028576

22. Chembl277535

23. Qyj305z91o

24. Bifonazolum

25. Chebi:78692

26. 1-[biphenyl-4-yl(phenyl)methyl]-1h-imidazole

27. 1h-imidazole, 1-((1,1'-biphenyl)-4-ylphenylmethyl)-

28. (+-)1-([1,1'-biphenyl]-4-ylphenylmethyl)-1h-imidazole

29. Ncgc00018254-03

30. Smr000058970

31. 1-[biphenyl-4-yl(phenyl)methyl]imidazole

32. Dsstox_cid_25631

33. Dsstox_rid_81013

34. Dsstox_gsid_45631

35. Mycospor (tn)

36. Cas-60628-96-8

37. (+/-)-bifonazole

38. Sr-01000003136

39. Einecs 262-336-6

40. 1-(biphenyl-4-yl(phenyl)methyl)-1h-imidazole

41. Brn 0618427

42. Unii-qyj305z91o

43. Mycosporan

44. Bedriol

45. Bifonazole,(s)

46. Bifonazole [usan:inn:ban:jan]

47. Mfcd00865567

48. Cpd000058970

49. Bifonazole [mi]

50. Bifonazole [inn]

51. Bifonazole [jan]

52. Opera_id_1656

53. Spectrum2_000035

54. Spectrum3_001970

55. (.+/-.)-bifonazole

56. Bifonazole [usan]

57. Imidazole, 1-(alpha-(4-biphenylyl)benzyl)-

58. 1-((4-biphenylyl)-phenylmethyl)-1h-imidazole

59. 1-(biphenyl-4-yl-phenyl-methyl)-1h-imidazole

60. Bifonazole [mart.]

61. Cid_2378

62. Bifonazole [who-dd]

63. Schembl36803

64. Bspbio_003570

65. 5-23-04-00292 (beilstein Handbook Reference)

66. Mls000759537

67. Mls001074074

68. Mls001424050

69. Spectrum1505309

70. Spbio_000129

71. Bifonazole (jp17/usan/inn)

72. Bifonazole [ep Impurity]

73. Bifonazole, >=98% (hplc)

74. Dtxsid9045631

75. Bifonazole For System Suitability

76. Kbio3_002922

77. Bifonazole [ep Monograph]

78. Hms1922b18

79. Hms2051f04

80. Hms2090k13

81. Hms2093b09

82. Hms2232j24

83. Hms3374h02

84. Hms3393f04

85. Hms3651g21

86. Hms3715l21

87. Pharmakon1600-01505309

88. 1h-imidazole, 1-((1,1'-biphenyl)-4-ylphenylmethyl)-, (+-)-

89. Amy32554

90. Bcp22297

91. Hy-b0301

92. Tox21_110850

93. Bdbm50128548

94. Ccg-39996

95. Dl-338

96. Nsc758954

97. S1854

98. Stk618771

99. Akos005553008

100. Tox21_110850_1

101. Ab07497

102. Bcp9000410

103. Ccg-100993

104. Db04794

105. Ks-5111

106. Nc00243

107. Nsc 758954

108. Mrf-0000274

109. Ncgc00018254-02

110. Ncgc00018254-04

111. Ncgc00018254-05

112. Ncgc00018254-08

113. Ncgc00018254-09

114. Ncgc00089815-02

115. Ncgc00089815-03

116. Ncgc00089815-04

117. Ac-15414

118. Bp164253

119. Sbi-0206755.p001

120. 1-(.alpha.-(4-biphenylyl)benzyl)imidazole

121. 1-(alpha,4-diphenylbenzyl)imidazole

122. 1-[alpha-(4-biphenylyl)-benzyl]-imidazole

123. (biphenyl-4-yl)-imidazol-1-yl-phenylmethane

124. B4173

125. Ft-0652733

126. Sw197623-3

127. Vu0239694-7

128. 1-[phenyl(4-phenylphenyl)methyl]-1h-imidazole

129. 28b968

130. D01775

131. Imidazole, 1-(.alpha.-(4-biphenylyl)benzyl)-

132. Ab00383029-16

133. Ab00383029_17

134. Ab00383029_18

135. (.+/-.)-1-(p,.alpha.-diphenylbenzyl)imidazole

136. A832816

137. Q421162

138. 1-(1-biphenyl-4-yl-2-phenyl-methyl)-1h-imidazole

139. Q-200717

140. Sr-01000003136-4

141. Sr-01000003136-6

142. (+/-)-1-(p,.alpha.-diphenylbenzyl)imidazole

143. 1-[phenyl-(4-phenylphenyl)methyl]imidazole;bifonazole

144. Brd-a94543220-001-02-3

145. Brd-a94543220-001-12-2

146. 1-(biphenyl-4-yl-phenyl-methyl)-1h-imidazole (bifonazole)

147. 1-(biphenyl-4-yl-phenyl-methyl)-1h-imidazole( Bifanozole)

148. 1-(biphenyl-4-yl-phenyl-methyl)-1h-imidazole(bifonazole)

149. 1-[[1,1'-biphenyl]-4-yl(phenyl)methyl]-1h-imidazole #

150. Bifonazole, European Pharmacopoeia (ep) Reference Standard

151. 1h-imidazole, 1-([1,1'-biphenyl]-4-ylphenylmethyl)-, (.+/-.)-

152. 1h-imidazole, 1-((1,1'-biphenyl)-4-ylphenylmethyl)-, (+/-)-

153. Bifonazole, Pharmaceutical Secondary Standard; Certified Reference Material

154. Bifonazole For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₈N₂
Molecular Weight	310.4 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	4
Exact Mass	310.146998583 g/mol
Monoisotopic Mass	310.146998583 g/mol
Topological Polar Surface Area	17.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	362
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
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 for the treatment of various topical fungal infections, including athlete's foot (tinea pedis).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bifonazole is a type of antifungal medicine known as an imidazole. It kills fungi and yeasts by interfering with their cell membranes.

5.2 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

5.3 ATC Code

D01AC10

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AC - Imidazole and triazole derivatives

D01AC10 - Bifonazole

5.4 Absorption, Distribution and Excretion

Absorption

Very low absorption following topical administration (0.6% of an applied dose). In cases of skin lesions absorption is increased (2.5%).

5.5 Metabolism/Metabolites

Hepatic.

5.6 Biological Half-Life

1-2 hours

5.7 Mechanism of Action

Bifonazole works by inhibiting the production of a substance called ergosterol, which is an essential component of fungal cell membranes.It acts to destabilize the fungal cyctochrome p450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. The disruption in production of ergosterol disrupts the cell membrane and causes holes to appear. The cell membranes of fungi are vital for their survival. They keep unwanted substances from entering the cells and stop the contents of the cells from leaking out. As bifonazole causes holes to appear in the cell membranes, essential constituents of the fungal cells can leak out. This kills the fungi.