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    Oxiconazole Nitrate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Oxistat, Myfungar, Oceral, 64211-46-7, Sgd 301-76, St 813
    Molecular Formula
    C18H14Cl4N4O4
    Molecular Weight
    492.1  g/mol
    InChI Key
    WVNOAGNOIPTWPT-NDUABGMUSA-N
    FDA UNII
    RQ8UL4C17S
    Oxiconazole Nitrate is the nitrate salt form of oxiconazole, a broad spectrum imidazole derivative with antifungal activity. Although the exact mechanism of action has yet to be fully elucidated, oxiconazole, like other azole antifungals, most likely inhibits the cytochrome P450-dependent demethylation of lanosterol. This prevents the synthesis of ergosterol which is a crucial component of fungal cell membrane. By disrupting fungal cell membrane synthesis and integrity, oxiconazole alters fungal cell membrane permeability, promotes loss of essential intracellular components and eventually inhibits fungal cell growth.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (Z)-1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-ylethanimine;nitric acid
    2.1.2 InChI
    InChI=1S/C18H13Cl4N3O.HNO3/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22;2-1(3)4/h1-8,11H,9-10H2;(H,2,3,4)/b24-18+;
    2.1.3 InChI Key
    WVNOAGNOIPTWPT-NDUABGMUSA-N
    2.1.4 Canonical SMILES
    C1=CC(=C(C=C1Cl)Cl)CON=C(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]
    2.1.5 Isomeric SMILES
    C1=CC(=C(C=C1Cl)Cl)CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    RQ8UL4C17S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (z)-1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)-o-(2,4-dichlorobenzyl) Ethanone Oxime Nitrate

    2. 2',4'-dichloro-2-imidazol-1-ylacetophenone (z)-(o-(2,4-dichlorobenzyl)oxime), Mononitrate

    3. Fonx

    4. Gyno-myfungar

    5. Myfungar

    6. Oceral

    7. Oxiconazole

    8. Oxiconazole Mononitrate, (z)-isomer

    9. Oxistat

    10. Oxizole

    11. Oxyconazole

    12. Ro-13-8996

    13. Salongo

    14. Sgd 301-76

    2.3.2 Depositor-Supplied Synonyms

    1. Oxistat

    2. Myfungar

    3. Oceral

    4. 64211-46-7

    5. Sgd 301-76

    6. St 813

    7. Einecs 264-730-3

    8. St-813

    9. Ro-13-8996

    10. Nsc-758958

    11. Sgd-301-76

    12. Rq8ul4c17s

    13. 2',4'-dichloro-2-imidazol-1-ylacetophenone (z)-(o-(2,4-dichlorobenzyl)oxime), Mononitrate

    14. Chebi:7826

    15. Ro 13-8996

    16. Ethanone, 1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)-, O-((2,4-dichlorophenyl)methyl)oxime, (z)-, Mononitrate

    17. Ncgc00095170-01

    18. Dsstox_cid_25943

    19. Dsstox_rid_81241

    20. Dsstox_gsid_45943

    21. Ethanone, 1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)-,o-[(2,4-dichlorophenyl)methyl]oxime, (1z)-, Mononitrate

    22. Cas-64211-46-7

    23. Oxiconazole Nitrate [usan:jan]

    24. (z)-1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)ethanone O-(2,4-dichlorobenzyl) Oxime Nitrate

    25. Sr-05000002005

    26. 64211-45-6

    27. Unii-rq8ul4c17s

    28. Okinazole

    29. Oxiconazole Mono-nitrate (z)-isomer

    30. Oxistat (tn)

    31. Oxiconazole Nitrate- Bio-x

    32. 2',4'-dichloro-2-imidazol-1-ylacetophenone (z)-(o-(2,4-dichlorobenzyl))oxime Nitrate

    33. Mls001424103

    34. Schembl153416

    35. Schembl153417

    36. Spectrum1505330

    37. Sgd-30176

    38. Chembl1200836

    39. Dtxsid2045943

    40. Oxiconazole Nitrate [mi]

    41. Oxiconazole Nitrate (jan/usan)

    42. Oxiconazole Nitrate [jan]

    43. Hms1922d18

    44. Hms2093b21

    45. Hms3714a13

    46. Oxiconazole Nitrate [usan]

    47. Pharmakon1600-01505330

    48. Hy-b1324

    49. Oxiconazole Nitrate [mart.]

    50. Tox21_111467

    51. Ccg-40020

    52. Mfcd01727545

    53. Nsc758958

    54. Oxiconazole Nitrate [usp-rs]

    55. Oxiconazole Nitrate [who-dd]

    56. Akos016339564

    57. Tox21_111467_1

    58. Cs-7908

    59. Ks-5288

    60. Nsc 758958

    61. Ncgc00095170-02

    62. Ncgc00177980-03

    63. Oxiconazole Nitrate [orange Book]

    64. (z)-1-(2-(2,4-dichlorophenyl)-2-(((2,4-dichlorophenyl)oxy)imino)ethyl)-1h-imidazole Mononitrate

    65. Bo164217

    66. Ethanone, 1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)-, O-((2,4-dichlorophenyl)methyl)oxime, Nitrate, (z)-

    67. Smr000469293

    68. Ro-13-8996/001

    69. C08075

    70. D00885

    71. Sr-05000002005-1

    72. Sr-05000002005-2

    73. Sr-05000002005-3

    74. (z)-1-(2,4-dichlorophenyl)-n-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-yl-ethanimine

    75. 2',4'-dichloro-2-imidazol-1-ylacetophenone (z)-[oo-(2,4-dichlorobenzyl)oxime] Mononitrate

    76. (1z)-n-[(2,4-dichlorobenzyl)oxy]-1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)ethanimine Nitrate

    77. 1-[(2z)-2-{[(2,4-dichlorobenzyl)oxy]imino}-2-(2,4-dichlorophenyl)ethyl]-1h-imidazol-3-ium Nitrate

    2.4 Create Date
    2006-10-23
    3 Chemical and Physical Properties
    Molecular Weight 492.1 g/mol
    Molecular Formula C18H14Cl4N4O4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass491.973966 g/mol
    Monoisotopic Mass489.976916 g/mol
    Topological Polar Surface Area106 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity506
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameOxistat
    PubMed HealthOxiconazole (On the skin)
    Drug ClassesAntifungal
    Drug LabelOXISTAT (oxiconazole nitrate cream) Cream, 1% and OXISTAT (oxiconazole nitrate lotion) Lotion, 1% formulations contain the antifungal active compound oxiconazole nitrate. Both formulations are for topical dermatologic use only.Chemically, oxicona...
    Active IngredientOxiconazole nitrate
    Dosage FormCream; Lotion
    RouteTopical
    Strengtheq 1% base
    Market StatusPrescription
    CompanyFougera Pharms

    2 of 2  
    Drug NameOxistat
    PubMed HealthOxiconazole (On the skin)
    Drug ClassesAntifungal
    Drug LabelOXISTAT (oxiconazole nitrate cream) Cream, 1% and OXISTAT (oxiconazole nitrate lotion) Lotion, 1% formulations contain the antifungal active compound oxiconazole nitrate. Both formulations are for topical dermatologic use only.Chemically, oxicona...
    Active IngredientOxiconazole nitrate
    Dosage FormCream; Lotion
    RouteTopical
    Strengtheq 1% base
    Market StatusPrescription
    CompanyFougera Pharms

    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]