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Oxiconazole

Synopsis, Chemistry

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CREAM;TOPICAL - EQ 1% BASE, LOTION;TOPICAL - EQ 1% BASE

CREAM;TOPICAL - EQ 1% BASE
LOTION;TOPICAL - EQ 1% BASE

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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 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

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 Formula	C₁₈H₁₄Cl₄N₄O₄
Molecular Weight	492.1 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	491.973966 g/mol
Monoisotopic Mass	489.976916 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	506
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Oxistat
PubMed Health	Oxiconazole (On the skin)
Drug Classes	Antifungal
Drug Label	OXISTAT (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 Ingredient	Oxiconazole nitrate
Dosage Form	Cream; Lotion
Route	Topical
Strength	eq 1% base
Market Status	Prescription
Company	Fougera Pharms

2 of 2
Drug Name	Oxistat
PubMed Health	Oxiconazole (On the skin)
Drug Classes	Antifungal
Drug Label	OXISTAT (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 Ingredient	Oxiconazole nitrate
Dosage Form	Cream; Lotion
Route	Topical
Strength	eq 1% base
Market Status	Prescription
Company	Fougera 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]