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    Chemistry

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    Also known as: 99592-39-9, Dermofix, Ertaczo, Zalain, Sertaconazole mononitrate, Ginedermofix
    Molecular Formula
    C20H16Cl3N3O4S
    Molecular Weight
    500.8  g/mol
    InChI Key
    HAAITRDZHUANGT-UHFFFAOYSA-N
    FDA UNII
    1DV05410M5
    Sertaconazole Nitrate
    Sertaconazole Nitrate is the nitrate salt form of sertaconazole, a synthetic imidazole derivative with antifungal property. Sertaconazole nitrate inhibits fungal cytochrome P-450 sterol C-14 alpha-demethylation, resulting in the accumulation of fungal 14 alpha-methyl sterols and the inhibition of ergosterol synthesis, an essential component of the cell membrane of fungi. This leads to a disruption of cell membrane permeability and leakage of adenine triphosphate (ATP) and other constituents from fugal cells.
    1 2D Structure

    Sertaconazole Nitrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid
    2.1.2 InChI
    InChI=1S/C20H15Cl3N2OS.HNO3/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22;2-1(3)4/h1-8,11-12,19H,9-10H2;(H,2,3,4)
    2.1.3 InChI Key
    HAAITRDZHUANGT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC2=C(C(=C1)Cl)SC=C2COC(CN3C=CN=C3)C4=C(C=C(C=C4)Cl)Cl.[N+](=O)(O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    1DV05410M5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Dermofix

    2. Dermoseptic

    3. Ginedermofix

    4. Mykosert

    5. Sertaconazole

    6. Sertaconazole Mononitrate

    7. Zalain

    2.3.2 Depositor-Supplied Synonyms

    1. 99592-39-9

    2. Dermofix

    3. Ertaczo

    4. Zalain

    5. Sertaconazole Mononitrate

    6. Ginedermofix

    7. Dermovit

    8. Fi 7056

    9. Sertaconazole (nitrate)

    10. Fi-7045

    11. 99592-39-9 (nitrate)

    12. 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric Acid

    13. 1dv05410m5

    14. Fi-7056

    15. 1-[2-[(7-chloro-1-benzothien-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole Nitrate

    16. 1h-imidazole, 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-, Mononitrate

    17. Dermoseptic

    18. 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1h-imidazole; Nitric Acid

    19. Fisderm

    20. Extens

    21. Onabet

    22. Sr-05000001439

    23. Unii-1dv05410m5

    24. Sertaconazolenitrate

    25. Ertaczo (tn)

    26. Zalain (tn)

    27. 1-(2-((7-chlorobenzo[b]thiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole Nitrate

    28. 1h-imidazole, 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-, Nitrate (1:1)

    29. Ncgc00016966-01

    30. Cas-99592-39-9

    31. Dsstox_cid_25529

    32. Dsstox_rid_80932

    33. Dsstox_gsid_45529

    34. Mls002154122

    35. Schembl261807

    36. Chembl1200725

    37. Dtxsid2045529

    38. Hy-b0736a

    39. Hms1571a12

    40. Hms2098a12

    41. Hms2231n14

    42. Hms3372h01

    43. Hms3715a12

    44. Sertaconazole Nitrate [mi]

    45. Amy32537

    46. Bcp09311

    47. Tox21_110718

    48. Ac-739

    49. Fi7056

    50. Mfcd00918063

    51. S3161

    52. Sertaconazole Nitrate [mart.]

    53. Akos015888158

    54. Akos015964610

    55. Sertaconazole Nitrate [who-dd]

    56. Ccg-221045

    57. 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole; Nitric Acid

    58. As-14332

    59. Smr001233429

    60. Sertaconazole Nitrate [orange Book]

    61. Sertaconazole Nitrate [ep Monograph]

    62. Ft-0674558

    63. D08510

    64. F20635

    65. A846049

    66. A851341

    67. Sr-05000001439-3

    68. Q27252298

    69. 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole Mononitrate

    70. 1-[2-[(7-chloranyl-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole; Nitric Acid

    71. 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole,nitric Acid

    2.3.3 Other Synonyms

    1. Sertaconazole

    2. Sertaconazol

    3. Demofix

    2.4 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 500.8 g/mol
    Molecular Formula C20H16Cl3N3O4S
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass498.992710 g/mol
    Monoisotopic Mass498.992710 g/mol
    Topological Polar Surface Area121 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity513
    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 2  
    Drug NameErtaczo
    PubMed HealthSertaconazole (On the skin)
    Drug ClassesAntifungal
    Drug LabelERTACZO (sertaconazole nitrate) Cream, 2%, contains the imidazole antifungal, sertaconazole nitrate. Sertaconazole nitrate contains one asymmetric carbon atom and exists as a racemic mixture of equal amounts of R and S enantiomers.Sertaconazole nit...
    Active IngredientSertaconazole nitrate
    Dosage FormCream
    RouteTopical
    Strength2%
    Market StatusPrescription
    CompanyValeant Luxembourg

    2 of 2  
    Drug NameErtaczo
    PubMed HealthSertaconazole (On the skin)
    Drug ClassesAntifungal
    Drug LabelERTACZO (sertaconazole nitrate) Cream, 2%, contains the imidazole antifungal, sertaconazole nitrate. Sertaconazole nitrate contains one asymmetric carbon atom and exists as a racemic mixture of equal amounts of R and S enantiomers.Sertaconazole nit...
    Active IngredientSertaconazole nitrate
    Dosage FormCream
    RouteTopical
    Strength2%
    Market StatusPrescription
    CompanyValeant Luxembourg

    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]

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    06-Jan-2021
    14-Sep-2024
    KGS
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