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Butoconazole Nitrate

Synopsis, 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 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 Formula	C₁₉H₁₈Cl₃N₃O₃S
Molecular Weight	474.8 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	473.013446 g/mol
Monoisotopic Mass	473.013446 g/mol
Topological Polar Surface Area	109 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	408
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Butoconazole nitrate
Active Ingredient	Butoconazole nitrate
Dosage Form	Cream
Route	Vaginal
Strength	2%
Market Status	Prescription
Company	Perrigo Israel

2 of 4
Drug Name	Femstat 3
Drug Label	GYNAZOLE 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 Ingredient	Butoconazole nitrate
Dosage Form	Cream
Route	Vaginal
Strength	2%
Market Status	Over the Counter
Company	Bayer

3 of 4
Drug Name	Butoconazole nitrate
Active Ingredient	Butoconazole nitrate
Dosage Form	Cream
Route	Vaginal
Strength	2%
Market Status	Prescription
Company	Perrigo Israel

4 of 4
Drug Name	Femstat 3
Drug Label	GYNAZOLE 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 Ingredient	Butoconazole nitrate
Dosage Form	Cream
Route	Vaginal
Strength	2%
Market Status	Over the Counter
Company	Bayer

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]