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    Chemistry

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    Also known as: 64872-77-1, Femstat, Gynomyk, Gynazole-1, Rs-35887, Butoconazole (nitrate)
    Molecular Formula
    C19H18Cl3N3O3S
    Molecular Weight
    474.8  g/mol
    InChI Key
    ZHPWRQIPPNZNML-UHFFFAOYSA-N
    FDA UNII
    4805237NP5
    Butoconazole Nitrate
    Butoconazole Nitrate is the nitrate salt form of butaconazole, a synthetic imidazole derivative with fungistatic properties. Butoconazole nitrate interferes with steroid biosynthesis by inhibiting the conversion of lanosterol to ergosterol, thereby changing the fungal cell membrane lipid composition. This alters cell permeability and leads to growth inhibition. Butaconazole nitrate is active against many dermatophytes and yeasts. It also contains antibacterial effects against some gram-positive organisms.
    1 2D Structure

    Butoconazole Nitrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole;nitric acid
    2.1.2 InChI
    InChI=1S/C19H17Cl3N2S.HNO3/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22;2-1(3)4/h1-5,7-8,10-11,13,16H,6,9,12H2;(H,2,3,4)
    2.1.3 InChI Key
    ZHPWRQIPPNZNML-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC(=C(C(=C1)Cl)SC(CCC2=CC=C(C=C2)Cl)CN3C=CN=C3)Cl.[N+](=O)(O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    4805237NP5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl)-1h-imidazole

    2. Butoconazole

    3. Femstal

    4. Femstat

    5. Gynazole-1

    6. Gynomyk

    7. Mycelex-3

    8. Rs 35887

    2.3.2 Depositor-Supplied Synonyms

    1. 64872-77-1

    2. Femstat

    3. Gynomyk

    4. Gynazole-1

    5. Rs-35887

    6. Butoconazole (nitrate)

    7. Gynazole

    8. Rs 35887

    9. Butaconazole Nitrate

    10. Rs-35887-00-10-3

    11. Chebi:3241

    12. 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1h-imidazole Nitrate

    13. 1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole;nitric Acid

    14. Mycelex-3

    15. (+-)-1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1h-imidazole Mononitrate

    16. (+-)-1-(4-(p-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)imidazole Mononitrate

    17. Exelgyn

    18. 4805237np5

    19. Femstat One

    20. 1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole Nitrate

    21. 1-{4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl}-1h-imidazole Nitrate

    22. Dsstox_cid_25452

    23. Dsstox_rid_80888

    24. Dsstox_gsid_45452

    25. Mls002153798

    26. 1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)butyl)-1h-imidazole Nitrate

    27. Butoconazole Nitrate [usan]

    28. Cas-64872-77-1

    29. Mfcd00058159

    30. Smr001233176

    31. Butoconazole Nitrate [usan:usp]

    32. Unii-4805237np5

    33. Femstat (tn)

    34. Gynazole-1 (tn)

    35. Nitrato De Butoconazol

    36. Ncgc00016812-01

    37. Butoconazole Nitrate (usp)

    38. Schembl41394

    39. Chembl1200398

    40. Dtxsid6045452

    41. Amy8930

    42. Butoconazole Nitrate [mi]

    43. Hms1569a18

    44. Hms2096a18

    45. Hms2234a19

    46. Hms3370o18

    47. Hms3655a16

    48. Hms3713a18

    49. Act06285

    50. Bcp02595

    51. Hy-b0293

    52. Butoconazole Nitrate [vandf]

    53. Tox21_110624

    54. Ac-199

    55. Butoconazole Nitrate [mart.]

    56. S1833

    57. Butoconazole Nitrate [usp-rs]

    58. Butoconazole Nitrate [who-dd]

    59. Akos015855542

    60. Akos015964937

    61. Tox21_110624_1

    62. Butoconazole Nitrate, >=90% (hplc)

    63. Ccg-220408

    64. Ncgc00179596-03

    65. 1h-imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (+-)-, Mononitrate

    66. 1h-imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, Mononitrate, (+-)-

    67. As-14137

    68. Butoconazole Nitrate [orange Book]

    69. Butoconazole Nitrate [usp Monograph]

    70. B4801

    71. Ft-0653569

    72. Sw197153-3

    73. C08066

    74. D00880

    75. Sr-01000841222

    76. Sr-01000841222-2

    77. Q27105999

    78. 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]imidazole Nitrate

    79. Butoconazole Nitrate, United States Pharmacopeia (usp) Reference Standard

    80. 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1h-imidazolenitrate

    81. 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1h-imidazole Nitrate;rs-35887

    82. 1-{4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl}-1h-imidazole Nitrate

    83. Butoconazole Nitrate, Pharmaceutical Secondary Standard; Certified Reference Material

    84. (+/-)-1-(4-(p-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)imidazole Mononitrate

    85. 1h-imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, Mononitrate, (+/-)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 474.8 g/mol
    Molecular Formula C19H18Cl3N3O3S
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass473.013446 g/mol
    Monoisotopic Mass473.013446 g/mol
    Topological Polar Surface Area109 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity408
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameButoconazole nitrate
    Active IngredientButoconazole nitrate
    Dosage FormCream
    RouteVaginal
    Strength2%
    Market StatusPrescription
    CompanyPerrigo Israel

    2 of 4  
    Drug NameFemstat 3
    Drug LabelGYNAZOLE 1 Butoconazole Nitrate Vaginal Cream USP, 2% contains butoconazole nitrate 2%, an imidazole derivative with antifungal activity. Its chemical name is ()-1-[4- (p-chlorophenyl)-2- [(2,6-dichlorophenyl) thio]butyl] imidazole mononitrat...
    Active IngredientButoconazole nitrate
    Dosage FormCream
    RouteVaginal
    Strength2%
    Market StatusOver the Counter
    CompanyBayer

    3 of 4  
    Drug NameButoconazole nitrate
    Active IngredientButoconazole nitrate
    Dosage FormCream
    RouteVaginal
    Strength2%
    Market StatusPrescription
    CompanyPerrigo Israel

    4 of 4  
    Drug NameFemstat 3
    Drug LabelGYNAZOLE 1 Butoconazole Nitrate Vaginal Cream USP, 2% contains butoconazole nitrate 2%, an imidazole derivative with antifungal activity. Its chemical name is ()-1-[4- (p-chlorophenyl)-2- [(2,6-dichlorophenyl) thio]butyl] imidazole mononitrat...
    Active IngredientButoconazole nitrate
    Dosage FormCream
    RouteVaginal
    Strength2%
    Market StatusOver the Counter
    CompanyBayer

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Azoles [CS]; Azole Antifungal [EPC]

    API Reference Price

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    30-Apr-2024
    30-Apr-2024
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