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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
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

Oxiconazole Nitrate

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]

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30-Jan-2021
06-May-2024
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Topical

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Solubilizers

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Emulsifying Agents

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Thickeners and Stabilizers

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Surfactant & Foaming Agents

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Film Formers & Plasticizers

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Lubricants & Glidants

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Parenteral

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Granulation

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Direct Compression

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Digital Content read-more

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DATA COMPILATION #PharmaFlow

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NEWS #PharmaBuzz

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Market Place

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REF. STANDARDS & IMPURITIES

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