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2D Structure
Also known as: 64872-76-0, Butaconazole, Butoconazol, Butoconazolum, Butoconazol [inn-spanish], Butoconazolum [inn-latin]
Molecular Formula
C19H17Cl3N2S
Molecular Weight
411.8  g/mol
InChI Key
SWLMUYACZKCSHZ-UHFFFAOYSA-N
FDA UNII
0Q771797PH

Butoconazole is a synthetic imidazole derivative with fungistatic properties. Butoconazole 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.
Butoconazole is an Azole Antifungal.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
2.1.2 InChI
InChI=1S/C19H17Cl3N2S/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/h1-5,7-8,10-11,13,16H,6,9,12H2
2.1.3 InChI Key
SWLMUYACZKCSHZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C(=C1)Cl)SC(CCC2=CC=C(C=C2)Cl)CN3C=CN=C3)Cl
2.2 Other Identifiers
2.2.1 UNII
0Q771797PH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl)-1h-imidazole

2. Butoconazole Nitrate

3. Femstal

4. Femstat

5. Gynazole-1

6. Gynomyk

7. Mycelex-3

8. Rs 35887

2.3.2 Depositor-Supplied Synonyms

1. 64872-76-0

2. Butaconazole

3. Butoconazol

4. Butoconazolum

5. Butoconazol [inn-spanish]

6. Butoconazolum [inn-latin]

7. Gynofort

8. Butoconazole (inn)

9. Gynazole-1

10. Nsc-758658

11. Chebi:3240

12. 0q771797ph

13. Butoconazole [inn]

14. Butoconazole [inn:ban]

15. Mls002153798

16. 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1h-imidazole

17. 1-[4-(4-chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1h-imidazole

18. 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1h-imidazole

19. 1h-imidazole, 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-

20. Gynofort (tn)

21. Smr001233176

22. Rs 35887-10-3

23. Unii-0q771797ph

24. 67085-13-6

25. Prestwick0_000408

26. Prestwick1_000408

27. Prestwick2_000408

28. Prestwick3_000408

29. Butoconazole [mi]

30. 1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole

31. 1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole

32. 1-{4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl}-1h-imidazole

33. Butoconazole [vandf]

34. Chembl1295

35. Schembl44237

36. Bspbio_000336

37. Cid_47471

38. Mls006010743

39. Butoconazole [who-dd]

40. Spbio_002275

41. Bpbio1_000370

42. 1-[(2s)-4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole

43. Dtxsid2048537

44. Bdbm79206

45. Hy-b0293a

46. Hms3264e14

47. Pharmakon1600-01504140

48. Albb-028967

49. Amy32540

50. Butoconazole, Butoconazole Nitrate

51. (+-)-1-((4-(p-chlorophenyl)-2-((2,6-dichlorophenyl)thio)imidazole

52. Nsc758658

53. S5359

54. Akos015900067

55. Ccg-213264

56. Db00639

57. Nsc 758658

58. (+-)-1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1h-imidazole

59. 1h-imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (+-)-

60. Ncgc00179596-01

61. Ncgc00179596-04

62. Ac-15961

63. Smr001550002

64. Db-054743

65. Ab00513831

66. Cs-0013455

67. Ft-0630751

68. C08065

69. D07598

70. Ab00513831-07

71. Ab00513831_08

72. Ab00513831_09

73. Butoconazole, Vetranal(tm), Analytical Standard

74. 872b760

75. A834909

76. Q2928948

77. Brd-a16665823-001-01-2

78. Brd-a16665823-008-03-3

79. 1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)butyl)-1h-imidazole

80. 1-[2-[(2,6-dichlorophenyl)thio]-4-(4-chlorophenyl)butyl]-1h-imidazole

81. 1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imid-azole

82. 1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-imidazole

83. (+/-)-1-(4-(p-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)imidazole

84. (.+/-.)-1-[4-(p-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]imidazole

85. 1-(4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl)-1h-imidazole #

86. 1h-imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (+/-)-

87. 1h-imidazole, 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-, (1)-

88. 1h-imidazole, 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-, Nitrate (1:1)

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 411.8 g/mol
Molecular Formula C19H17Cl3N2S
XLogP36.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count7
Exact Mass410.017803 g/mol
Monoisotopic Mass410.017803 g/mol
Topological Polar Surface Area43.1 Ų
Heavy Atom Count25
Formal Charge0
Complexity383
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the local treatment of vulvovaginal candidiasis (infections caused by Candida)


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Butoconazole is an imidazole derivative that has fungicidal activity in vitro against Candida spp. and has been demonstrated to be clinically effective against vaginal infections due to Candida albicans. Candida albicans has been identified as the predominant species responsible for vulvovaginal candidasis.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
BUTOCONAZOLE
5.3.2 FDA UNII
0Q771797PH
5.3.3 Pharmacological Classes
Chemical Structure [CS] - Azoles
5.4 ATC Code

G01AF15

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AF - Imidazole derivatives

G01AF15 - Butoconazole


5.5 Absorption, Distribution and Excretion

Absorption

Following vaginal administration of butoconazole nitrate vaginal cream, 2% to 3 women, 1.7% (range 1.3-2.2%) of the dose was absorbed on average.


5.6 Mechanism of Action

The exact mechanism of the antifungal action of butoconazole is unknown, however, it is presumed to function as other imidazole derivatives via inhibition of steroid synthesis. Imidazoles generally inhibit the conversion of lanosterol to ergosterol via the inhibition of the enzyme cytochrome P450 14α-demethylase, resulting in a change in fungal cell membrane lipid composition. This structural change alters cell permeability and, ultimately, results in the osmotic disruption or growth inhibition of the fungal cell.