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    Chemistry

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    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
    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

    Tioconazole

    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 Weight 387.7 g/mol
    Molecular Formula C16H13Cl3N2OS
    XLogP35.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count6
    Exact Mass385.981417 g/mol
    Monoisotopic Mass385.981417 g/mol
    Topological Polar Surface Area55.3 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity379
    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 Information
    1 of 4  
    Drug NameTioconazole
    PubMed HealthTioconazole (Topical route)
    Drug ClassesImidazole
    Active IngredientTioconazole
    Dosage FormOintment
    RouteVaginal
    Strength6.5%
    Market StatusOver the Counter
    CompanyPerrigo

    2 of 4  
    Drug NameVagistat-1
    Active IngredientTioconazole
    Dosage FormOintment
    RouteVaginal
    Strength6.5%
    Market StatusOver the Counter
    CompanyNovartis

    3 of 4  
    Drug NameTioconazole
    PubMed HealthTioconazole (Topical route)
    Drug ClassesImidazole
    Active IngredientTioconazole
    Dosage FormOintment
    RouteVaginal
    Strength6.5%
    Market StatusOver the Counter
    CompanyPerrigo

    4 of 4  
    Drug NameVagistat-1
    Active IngredientTioconazole
    Dosage FormOintment
    RouteVaginal
    Strength6.5%
    Market StatusOver the Counter
    CompanyNovartis

    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.

    API Reference Price

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    22-Jan-2021
    17-Sep-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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