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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 SUPPLIERS

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LGM Pharma

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Inabata France S.A.S

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Jai Radhe Sales

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Tenatra Chemie

India

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Solara Active Pharma Sciences

India

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Erregierre SpA

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Erregierre SpA

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Mitsubishi Corporation

Japan

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Mitsubishi Corporation

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Hengdian Group

China

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Precise Group

India

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Optimus Pharma

India

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Optimus Pharma

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USDMF

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Erregierre Spa

Italy

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Pfizer Ltd

Japan

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Pfizer Ltd

Japan
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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 4881

Submission : 1983-10-14

Status : Inactive

Type : II

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Tioconazole (Ph.Eur)

Date of Issue : 2022-11-03

Valid Till : 2025-07-02

Written Confirmation Number : WC-0182

Address of the Firm : Sy.no. 239 and 240 Dothigudem Village, Pochampally mandal, Nalgonda, District-50...

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TIOCONAZOLE

NDC Package Code : 49706-1283

Start Marketing Date : 2010-01-08

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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TIOCONAZOLE

NDC Package Code : 49706-1282

Start Marketing Date : 2010-01-08

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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TIOCONAZOLE

NDC Package Code : 72643-029

Start Marketing Date : 2022-07-06

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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LGM Pharma

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Tioconazole

About the Company : LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, ...

LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, analytical method development and testing, and commercial manufacturing. LGM Pharma offers custom API synthesis, analytical development, and regulatory services. With a network of over 300 accredited CGMP manufacturing partners, LGM provides unparalleled supply chain security. And, with over 100,000 square feet of FDA-inspected cGMP manufacturing and warehouse capacity, LGM Pharma provides a one-stop solution for solid dose, powder, semi-solid and liquid drugs.
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About the Company : Established in 1990, Inabata France, a part of the Inabata Group, used to export chemical and pharmaceutical products to Japan. In 2006, it acquired Pharmasynthèse. Today, Inabata...

Established in 1990, Inabata France, a part of the Inabata Group, used to export chemical and pharmaceutical products to Japan. In 2006, it acquired Pharmasynthèse. Today, Inabata-Pharmasynthèse offers a wide range of services, including sourcing, manufacturing, and the development of raw materials for the pharmaceutical and cosmetic industries. It supplies these ingredients to Europe, Japan, and other countries. With expertise in fine chemical production, Inabata-Pharmasynthèse conducts manufacturing operations, ranging from pilot to commercial quantities, at its GMP-certified facility at St. Pierre-Les-Elbeuf in France.
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About the Company : Jai Radhe Sales was founded in 1999 as an out-of-the-box distribution firm specializing in the global supply of high-quality pharmaceutical ingredients. The firm provides complete ...

Jai Radhe Sales was founded in 1999 as an out-of-the-box distribution firm specializing in the global supply of high-quality pharmaceutical ingredients. The firm provides complete sourcing solutions for pharmaceutical products from India, including technical and regulatory assistance. It believes in providing its customers with high-quality products at reasonable prices. It has always endeavored to achieve global standards in the field of pharmaceuticals and has carved out a niche for itself through new methods based on current market needs. Today, it has established itself as a truly global company, with exports to almost every continent.
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Tioconazole

About the Company : Tenatra International was established as a proprietorship firm in 1999. It got off to a very good start, supporting clients in the United States, Mexico and Europe. As business opp...

Tenatra International was established as a proprietorship firm in 1999. It got off to a very good start, supporting clients in the United States, Mexico and Europe. As business opportunities grew, it was felt that the proprietorship firm had outlived its usefulness and that it needed a corporate structure. So, Tenatra Chemie Private Limited (TCPL) was incorporated in 2002. Since then, the company has come a long way, gaining valuable experience and knowledge in the fields of chemicals and pharmaceuticals in India.
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About the Company : Aspire group was established in the year 2000 with a motto of quality drug for better health of all. In its journey till date, aspire has developed enormous reputation, consistent ...

Aspire group was established in the year 2000 with a motto of quality drug for better health of all. In its journey till date, aspire has developed enormous reputation, consistent growth, unique technologies and world class quality healthcare products. Aspire is pioneer in manufacturing and sourcing unique healthcare products. True to the statement, “Where the future started yesterday” with a foresight on the current trends in the healthcare market, Aspire has grown from strength combining its research strength, Human resources and well established quality systems. Aspire has crossed numerous milestones in a comparatively short period since its inception.
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About the Company : HENGDIAN GROUP was established in 1975, till now it has become a transnational,conglomerate group and been one of the largest private-owned enterprises in China. The Pharmaceutical...

HENGDIAN GROUP was established in 1975, till now it has become a transnational,conglomerate group and been one of the largest private-owned enterprises in China. The Pharmaceutical & Chemical division has 3 sub-companies with over 3,000 employees of which over 30% are technicians; This division is mainly producing APIs, Agrochemical and Dyestuffs with related intermediates as well as other special chemicals. The group also focuses on CONTRACT MANUFACTURE service under GMP and confidential agreement with our clients.
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Tioconazole

About the Company : Hermes Chemical Company Pvt Ltd is a chemicals company established in 2001 and headquartered in Hyderabad. It is specialized in developing, manufacturing, and selling complex molec...

Hermes Chemical Company Pvt Ltd is a chemicals company established in 2001 and headquartered in Hyderabad. It is specialized in developing, manufacturing, and selling complex molecules. The core competence of Hermes lies in its ability to develop and deliver niche molecules from gram scales to multi-ton levels. They have been credited with being the first company in India to manufacture N-Butyl Lithium, Montelukast Intermediates, Donepezil Intermediates, and Biperiden Hydrochloride.
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Tioconazole

About the Company : Optimus is one of the fastest-growing pharmaceutical companies with 16 years of experience in providing the best quality of API, Intermediates & Finished formulations in Global mar...

Optimus is one of the fastest-growing pharmaceutical companies with 16 years of experience in providing the best quality of API, Intermediates & Finished formulations in Global markets. Our aim from day one has been to provide and ensure better healthcare across the globe through our research, Innovations, affordable products & manufacturing excellence. Optimus was established to provide quality & affordable pharmaceutical products in the global markets.
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Tioconazole

About the Company : Indian Pharmaceutical Company, Precise Group is emerging as a global player in several verticals in healthcare. The Mumbai based drug manufacturing company’s strength lies in a s...

Indian Pharmaceutical Company, Precise Group is emerging as a global player in several verticals in healthcare. The Mumbai based drug manufacturing company’s strength lies in a strong network of industry professionals who care capable of handling the development of APIs, several Ready-to-fill Pellets and other intermediates, and chemicals. The company’s influence has a universal reach coordinating with multi-levels of global healthcare service providers for generic drugs. It holds a valued equity in niche pharma sectors in USA, Europe and Africa. Precise Group’s business encompasses the protection of the interest of their shareholders, is complaint with international regulatory bodies and meets the protocol favored in any region as a pharma suppler spanning developed and new markets. The technologically advanced manufacturing hub near Mumbai conducts manufacturing programs to sustain quality drugs at cost effect prices.
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Refarmed Chemicals

Switzerland
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Refarmed Chemicals

Switzerland
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Tioconazole

About the Company : Refarmed Chemicals is a fully integrated Swiss-based marketing company with extensive experience in the generics industry. Our global market activity and strategic offices located ...

Refarmed Chemicals is a fully integrated Swiss-based marketing company with extensive experience in the generics industry. Our global market activity and strategic offices located in India and China give customers the benefit of our expertise in API sourcing, finished formulation and new product development, technical and regulatory support, supply chain logistics, out-licensing and other business development activities. Our presence in over 60 countries gives us a vast network to monitor the latest market developments.
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30-Jan-2021
22-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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