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1-[2-[(2-Chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)-ethyl]imidazole; Vagistat

1-[2-[(2-Chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)-ethyl]imidazole; Vagistat

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1-[2-[(2-Chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)-ethyl]imidazole; Vagistat

Also known as: 65899-73-2, Vagistat, Vagistat-1, Trosyd, Trosyl, Gyno-trosyd

Molecular Formula

C₁₆H₁₃Cl₃N₂OS

Molecular Weight

387.7 g/mol

InChI Key

QXHHHPZILQDDPS-UHFFFAOYSA-N

FDA UNII

S57Y5X1117

Tioconazole is a synthetic imidazole derivative, fungicidal Terconazole inhibits cell wall synthesis by inhibiting the biosynthesis of ergosterol or other sterols, damaging the fungal cell membrane, altering its permeability, and promoting loss of essential intracellular elements. Tioconazole is active against pathogenic Candida. (NCI04)

Tioconazole is an Azole Antifungal.

1 2D Structure

1-[2-[(2-Chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)-ethyl]imidazole; Vagistat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole

2.1.2 InChI

InChI=1S/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2

2.1.3 InChI Key

QXHHHPZILQDDPS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1Cl)Cl)C(CN2C=CN=C2)OCC3=C(SC=C3)Cl

2.2 Other Identifiers

2.2.1 UNII

S57Y5X1117

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Gyno-trosyd

2. Monistat 1-day

3. Mykontral

4. Trosderm

5. Trosid

6. Trosyd

7. Trosyl

8. Uk 20,349

9. Vagistat

10. Vagistat-1

2.3.2 Depositor-Supplied Synonyms

1. 65899-73-2

2. Vagistat

3. Vagistat-1

4. Trosyd

5. Trosyl

6. Gyno-trosyd

7. Fungibacid

8. Zoniden

9. Tioconazol [inn-spanish]

10. Tioconazolum [inn-latin]

11. Uk-20349

12. 1-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole

13. Uk-20,349

14. Tioconazolum

15. Nsc-759169

16. 1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole

17. Tioconazol

18. Chebi:77898

19. Mfcd00057276

20. S57y5x1117

21. Ncgc00167430-01

22. Tz-3

23. 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole

24. 1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1h-imidazole

25. 1h-imidazole, 1-(2-((2-chloro-3-thienyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-

26. Dsstox_cid_26619

27. Dsstox_rid_81771

28. Dsstox_gsid_46619

29. New Straitus

30. 1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole

31. Smr001550005

32. (+-)-tioconazole

33. Cas-65899-73-2

34. Vagistat-1 (tn)

35. Uk 20349

36. Sr-05000001939

37. Einecs 265-973-8

38. Brn 0573867

39. Tioconazole (jan/usp/inn)

40. Unii-s57y5x1117

41. 1h-imidazole, 1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-

42. 1-[(2s)-2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole

43. 1-(2,4-dichloro-beta-((2-chloro-3-thenyl)-oxy)phenethyl)imidazole

44. (+-)-1-(2,4-dichloro-beta-((2-chloro-3-ethenyl)oxy)phenethyl)imidazole

45. Tioconazole, 97%

46. Tioconazole [usan:usp:inn:ban:jan]

47. Tioconazole [mi]

48. 1-(2,4-dichloro-(beta-(2-chloro-3-thenyl)oxy)phenethyl)imidazole

49. Tioconazole [inn]

50. Tioconazole [jan]

51. (.+/-.)-tioconazole

52. Tioconazole [inci]

53. Tioconazole [usan]

54. Tioconazole [vandf]

55. Tioconazole [mart.]

56. Schembl41354

57. Tioconazole [usp-rs]

58. Tioconazole [who-dd]

59. 5-23-04-00324 (beilstein Handbook Reference)

60. Mls003899209

61. Mls004712040

62. Mls006010907

63. Chembl1200438

64. Dtxsid3046619

65. Tioconazole [orange Book]

66. Tioconazole For System Suitability

67. Hms2090b12

68. Hms2093p11

69. Hms3655k22

70. Hms3712i10

71. Pharmakon1600-01505581

72. Tioconazole [ep Monograph]

73. Tioconazole [usp Impurity]

74. Tioconazole [usp Monograph]

75. Amy32535

76. Hy-b0319

77. Tox21_112434

78. Bdbm50370218

79. Dl-515

80. Nsc759169

81. S1910

82. Akos015906500

83. Tox21_112434_1

84. Ccg-213487

85. Db01007

86. Ks-5114

87. Nsc 759169

88. (+-)-1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole

89. Ncgc00167430-02

90. Ncgc00167430-03

91. Ncgc00167430-04

92. Ac-13425

93. Ac-31721

94. Sbi-0206824.p001

95. Ft-0630756

96. Sw198590-2

97. C08082

98. D00890

99. D83125

100. Ab01275523-01

101. Ab01275523_02

102. Ab01275523_03

103. Tioconazole, Vetranal(tm), Analytical Standard

104. 899t732

105. A835270

106. Q260326

107. Sr-05000001939-1

108. Sr-05000001939-2

109. Brd-a33084557-001-01-7

110. Tioconazole, United States Pharmacopeia (usp) Reference Standard

111. 1-[2,4-dichloro-.beta.-[(2-chloro-3-thenyl)-oxy]phenethyl]imidazole

112. (.+/-.)-1-(2,4-dichloro-.beta.-((2-chloro-3-ethenyl)oxy)phenethyl)imidazole

113. 1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole #

114. 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1h-imidazole

115. Tioconazole For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₃Cl₃N₂OS
Molecular Weight	387.7 g/mol
XLogP3	5.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	385.981417 g/mol
Monoisotopic Mass	385.981417 g/mol
Topological Polar Surface Area	55.3 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	379
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	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Tioconazole
PubMed Health	Tioconazole (Topical route)
Drug Classes	Imidazole
Active Ingredient	Tioconazole
Dosage Form	Ointment
Route	Vaginal
Strength	6.5%
Market Status	Over the Counter
Company	Perrigo

2 of 4
Drug Name	Vagistat-1
Active Ingredient	Tioconazole
Dosage Form	Ointment
Route	Vaginal
Strength	6.5%
Market Status	Over the Counter
Company	Novartis

3 of 4
Drug Name	Tioconazole
PubMed Health	Tioconazole (Topical route)
Drug Classes	Imidazole
Active Ingredient	Tioconazole
Dosage Form	Ointment
Route	Vaginal
Strength	6.5%
Market Status	Over the Counter
Company	Perrigo

4 of 4
Drug Name	Vagistat-1
Active Ingredient	Tioconazole
Dosage Form	Ointment
Route	Vaginal
Strength	6.5%
Market Status	Over the Counter
Company	Novartis

4.2 Drug Indication

For the local treatment of vulvovaginal candidiasis (moniliasis).

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tioconazole is a broad-spectrum imidazole antifungal agent that inhibits the growth of human pathogenic yeasts. Tioconazole exhibits fungicidal activity in vitro against Candida albicans, other species of the genus Candida, and against Torulopsis glabrata. Tioconazole prevents the growth and function of some fungal organisms by interfering with the production of substances needed to preserve the cell membrane. This drug is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.

5.2 MeSH Pharmacological Classification

14-alpha Demethylase Inhibitors

Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism. (See all compounds classified as 14-alpha Demethylase Inhibitors.)

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

TIOCONAZOLE

5.3.2 FDA UNII

S57Y5X1117

5.3.3 Pharmacological Classes

Azoles [CS]; Azole Antifungal [EPC]

5.4 ATC Code

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AC - Imidazole and triazole derivatives

D01AC07 - Tioconazole

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AF - Imidazole derivatives

G01AF08 - Tioconazole

5.5 Absorption, Distribution and Excretion

Absorption

Systemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.

5.6 Metabolism/Metabolites

Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.

5.7 Mechanism of Action

Tioconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Tioconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.