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    Bifonazole

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 311Xls

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    2D Structure
    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

    2D Structure

    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 Weight 310.4 g/mol
    Molecular Formula C22H18N2
    XLogP34.8
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count4
    Exact Mass310.146998583 g/mol
    Monoisotopic Mass310.146998583 g/mol
    Topological Polar Surface Area17.8 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity362
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.