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    Chemistry

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    Also known as: Ketoconazole, (+)-ketoconazole, 65277-42-1, (2r,4s)-ketoconazole, 142128-59-4, Kuric
    Molecular Formula
    C26H28Cl2N4O4
    Molecular Weight
    531.4  g/mol
    InChI Key
    XMAYWYJOQHXEEK-OZXSUGGESA-N
    Ketoconazole
    Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients.
    1 2D Structure

    Ketoconazole

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
    2.1.2 InChI
    InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1
    2.1.3 InChI Key
    XMAYWYJOQHXEEK-OZXSUGGESA-N
    2.1.4 Canonical SMILES
    CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
    2.1.5 Isomeric SMILES
    CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ketoconazole

    2. Nizoral

    3. R 41400

    4. R-41400

    5. R41,400

    6. R41400

    2.2.2 Depositor-Supplied Synonyms

    1. Ketoconazole

    2. (+)-ketoconazole

    3. 65277-42-1

    4. (2r,4s)-ketoconazole

    5. 142128-59-4

    6. Kuric

    7. Ketocanazole

    8. Cpd000058460

    9. Chembl75

    10. Smr000058460

    11. Mls000069784

    12. Mls001146934

    13. 1-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone

    14. 1-acetyl-4-(4-{[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine

    15. Chebi:48336

    16. Dsstox_cid_9879

    17. R-41400

    18. Dsstox_rid_78829

    19. Dsstox_gsid_29879

    20. 1-(4-(4-(((2r,4s)-2-((1h-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethanone

    21. Mfcd00058579

    22. Rac-trans-ketoconazole

    23. Ktz

    24. Sr-01000075626

    25. Sr-01000597381

    26. Ketoconazole (k)

    27. (+)-ketoconazol

    28. Ketoconazole,(s)

    29. Ncgc00016907-01

    30. Prestwick_744

    31. Cas-65277-42-1

    32. Tocris-1103

    33. Opera_id_397

    34. Prestwick0_000389

    35. Prestwick1_000389

    36. Prestwick2_000389

    37. Prestwick3_000389

    38. R 41,400

    39. Upcmld-dp138

    40. Schembl8407

    41. Lopac0_000666

    42. Bspbio_000577

    43. Mls000758224

    44. Mls001423987

    45. Mls002207053

    46. Mls002222255

    47. Bidd:gt0696

    48. Us9150527, Ketoconazole

    49. Spbio_002498

    50. Amy917

    51. Bdbm8610

    52. Bpbio1_000635

    53. Dtxsid7029879

    54. Upcmld-dp138:001

    55. Bdbm60666

    56. Hy-b0105a

    57. Ketoconazole, >=98% (hplc)

    58. Dtxsid901316748

    59. Hms1569m19

    60. Hms2051a19

    61. Hms2089n05

    62. Hms2096m19

    63. Hms2234h17

    64. Hms3262e13

    65. Hms3414j19

    66. Hms3678j17

    67. Hms3713m19

    68. Zinc643138

    69. Bcp28528

    70. Piperazine, (+/-)-1-acetyl-4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, Rel-

    71. Ketoconazole 2.0 Mg/ml In Methanol

    72. Tox21_110676

    73. Tox21_300267

    74. Tox21_500666

    75. Ei-107

    76. S1353

    77. Akos007930650

    78. Ccg-100815

    79. Cs-1846

    80. Ks-1205

    81. Lp00666

    82. Nc00065

    83. Sdccgsbi-0050645.p002

    84. Ketoconazole 100 Microg/ml In Methanol

    85. Mrf-0000100

    86. 24f2-1,25(oh)d3

    87. Ncgc00025000-01

    88. Ncgc00025000-02

    89. Ncgc00025000-03

    90. Ncgc00025000-04

    91. Ncgc00025000-05

    92. Ncgc00025000-06

    93. Ncgc00025000-07

    94. Ncgc00025000-08

    95. Ncgc00025000-09

    96. Ncgc00025000-10

    97. Ncgc00025000-14

    98. Ncgc00025000-16

    99. Ncgc00025000-28

    100. Ncgc00253967-01

    101. Ncgc00261351-01

    102. ( Inverted Exclamation Marka)-ketoconazol

    103. (+/-)-cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine

    104. Ac-15957

    105. Cis-1-acetyl-4-[4-[[2-(2,4-

    106. 3-dioxolan-4-yl)-methoxy]phenyl)piperazine

    107. Ketoconazole 100 Microg/ml In Acetonitrile

    108. Eu-0100666

    109. K0045

    110. Sw196888-4

    111. Bim-0050645.0001

    112. K 1003

    113. M02048

    114. 277k421

    115. Ketoconazole, Antibiotic For Culture Media Use Only

    116. Q-201267

    117. Sr-01000075626-1

    118. Sr-01000075626-4

    119. Sr-01000597381-1

    120. Sr-01000597381-6

    121. Brd-k29113274-001-03-6

    122. Brd-k29113274-001-11-9

    123. Brd-k29113274-001-21-8

    124. Q27121163

    125. (+)-r 41400

    126. Ketoconazole, British Pharmacopoeia (bp) Reference Standard

    127. Ketoconazole, European Pharmacopoeia (ep) Reference Standard

    128. Ketoconazole, United States Pharmacopeia (usp) Reference Standard

    129. Dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-piperazine

    130. Ketoconazole, Pharmaceutical Secondary Standard; Certified Reference Material

    131. (2r,4s)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine

    132. 1-(4-(4-(((2r,4s)-2-((1h-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one

    133. Cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl] Methoxy]phenyl]piperazine

    134. Kz

    135. Piperazine, (+)-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-

    2.3 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 531.4 g/mol
    Molecular Formula C26H28Cl2N4O4
    XLogP34.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count7
    Exact Mass530.1487608 g/mol
    Monoisotopic Mass530.1487608 g/mol
    Topological Polar Surface Area69.1 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity735
    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 Information
    1 of 10  
    Drug NameExtina
    PubMed HealthKetoconazole
    Drug LabelEXTINA Foam contains 2% ketoconazole USP, an antifungal agent, in a thermolabile hydroethanolic foam for topical application.The chemical name for ketoconazole is piperazine, 1-acetyl-4-[4-[[2-(2,4-dichlorophenyl) -2-(1H-imidazol-l-ylmethyl)-1,3-di...
    Active IngredientKetoconazole
    Dosage FormAerosol, foam
    RouteTopical
    Strength2%
    Market StatusPrescription
    CompanyDelcor Abet

    2 of 10  
    Drug NameKetoconazole
    PubMed HealthKetoconazole
    Drug LabelNIZORAL is a synthetic broad-spectrum antifungal agent available in scored white tablets, each containing 200 mg ketoconazole base for oral administration. Inactive ingredients are colloidal silicon dioxide, corn starch, lactose, magnesium stearate...
    Active IngredientKetoconazole
    Dosage FormShampoo; Tablet; Cream; Aerosol, foam
    RouteOral; Topical
    Strength200mg; 2%
    Market StatusPrescription
    CompanyTeva; Taro; Fougera Pharms; Perrigo New York; Tolmar; Mylan; Perrigo Israel

    3 of 10  
    Drug NameNizoral
    PubMed HealthKetoconazole
    Drug LabelNIZORAL is a synthetic broad-spectrum antifungal agent available in scored white tablets, each containing 200 mg ketoconazole base for oral administration. Inactive ingredients are colloidal silicon dioxide, corn starch, lactose, magnesium stearate...
    Active IngredientKetoconazole
    Dosage FormShampoo
    RouteTopical
    Strength2%
    Market StatusPrescription
    CompanyJanben Pharms

    4 of 10  
    Drug NameNizoral a-d
    PubMed HealthKetoconazole (On the skin)
    Active IngredientKetoconazole
    Dosage FormShampoo
    RouteTopical
    Strength1%
    Market StatusOver the Counter
    CompanyMcneil Cons

    5 of 10  
    Drug NameXolegel
    PubMed HealthKetoconazole
    Drug LabelXOLEGEL contains the antifungal agent ketoconazole USP at 2% in a topical anhydrous gel vehicle for topical administration.Chemically, ketoconazole is ()-cis-1-Acetyl-4-[p-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methox...
    Active IngredientKetoconazole
    Dosage FormGel
    RouteTopical
    Strength2%
    Market StatusPrescription
    CompanyAqua Pharms

    6 of 10  
    Drug NameExtina
    PubMed HealthKetoconazole
    Drug LabelEXTINA Foam contains 2% ketoconazole USP, an antifungal agent, in a thermolabile hydroethanolic foam for topical application.The chemical name for ketoconazole is piperazine, 1-acetyl-4-[4-[[2-(2,4-dichlorophenyl) -2-(1H-imidazol-l-ylmethyl)-1,3-di...
    Active IngredientKetoconazole
    Dosage FormAerosol, foam
    RouteTopical
    Strength2%
    Market StatusPrescription
    CompanyDelcor Abet

    7 of 10  
    Drug NameKetoconazole
    PubMed HealthKetoconazole
    Drug LabelNIZORAL is a synthetic broad-spectrum antifungal agent available in scored white tablets, each containing 200 mg ketoconazole base for oral administration. Inactive ingredients are colloidal silicon dioxide, corn starch, lactose, magnesium stearate...
    Active IngredientKetoconazole
    Dosage FormShampoo; Tablet; Cream; Aerosol, foam
    RouteOral; Topical
    Strength200mg; 2%
    Market StatusPrescription
    CompanyTeva; Taro; Fougera Pharms; Perrigo New York; Tolmar; Mylan; Perrigo Israel

    8 of 10  
    Drug NameNizoral
    PubMed HealthKetoconazole
    Drug LabelNIZORAL is a synthetic broad-spectrum antifungal agent available in scored white tablets, each containing 200 mg ketoconazole base for oral administration. Inactive ingredients are colloidal silicon dioxide, corn starch, lactose, magnesium stearate...
    Active IngredientKetoconazole
    Dosage FormShampoo
    RouteTopical
    Strength2%
    Market StatusPrescription
    CompanyJanben Pharms

    9 of 10  
    Drug NameNizoral a-d
    PubMed HealthKetoconazole (On the skin)
    Active IngredientKetoconazole
    Dosage FormShampoo
    RouteTopical
    Strength1%
    Market StatusOver the Counter
    Company<