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Chemistry

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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
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

Butoconazole

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.


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Butoconazole manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Butoconazole API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Butoconazole manufacturer or Butoconazole supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Butoconazole manufacturer or Butoconazole supplier.

PharmaCompass also assists you with knowing the Butoconazole API Price utilized in the formulation of products. Butoconazole API Price is not always fixed or binding as the Butoconazole Price is obtained through a variety of data sources. The Butoconazole Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Butoconazole

Synonyms

64872-76-0, Butaconazole, Butoconazol, Butoconazolum, Butoconazol [inn-spanish], Butoconazolum [inn-latin]

Cas Number

64872-77-1

Unique Ingredient Identifier (UNII)

0Q771797PH

About Butoconazole

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 Manufacturers

A Butoconazole manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Butoconazole, including repackagers and relabelers. The FDA regulates Butoconazole manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Butoconazole API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Butoconazole Suppliers

A Butoconazole supplier is an individual or a company that provides Butoconazole active pharmaceutical ingredient (API) or Butoconazole finished formulations upon request. The Butoconazole suppliers may include Butoconazole API manufacturers, exporters, distributors and traders.

click here to find a list of Butoconazole suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Butoconazole USDMF

A Butoconazole DMF (Drug Master File) is a document detailing the whole manufacturing process of Butoconazole active pharmaceutical ingredient (API) in detail. Different forms of Butoconazole DMFs exist exist since differing nations have different regulations, such as Butoconazole USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Butoconazole DMF submitted to regulatory agencies in the US is known as a USDMF. Butoconazole USDMF includes data on Butoconazole's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Butoconazole USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Butoconazole suppliers with USDMF on PharmaCompass.

Butoconazole GMP

Butoconazole Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Butoconazole GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Butoconazole GMP manufacturer or Butoconazole GMP API supplier for your needs.

Butoconazole CoA

A Butoconazole CoA (Certificate of Analysis) is a formal document that attests to Butoconazole's compliance with Butoconazole specifications and serves as a tool for batch-level quality control.

Butoconazole CoA mostly includes findings from lab analyses of a specific batch. For each Butoconazole CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Butoconazole may be tested according to a variety of international standards, such as European Pharmacopoeia (Butoconazole EP), Butoconazole JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Butoconazole USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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