Tioconazole
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MedKoo CAT#: 318876

CAS#: 65899-73-2

Description: Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. It is marketed under the brand names Trosyd and Gyno-Trosyd (Pfizer). Tioconazole ointments serve to treat women's vaginal yeast infections. Tioconazole topical (skin) preparations are also available for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus".


Chemical Structure

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Tioconazole
CAS# 65899-73-2

Theoretical Analysis

MedKoo Cat#: 318876
Name: Tioconazole
CAS#: 65899-73-2
Chemical Formula: C16H13Cl3N2OS
Exact Mass: 385.98142
Molecular Weight: 387.703
Elemental Analysis: C, 49.57; H, 3.38; Cl, 27.43; N, 7.23; O, 4.13; S, 8.27

Price and Availability

Size Price Availability Quantity
1.0g USD 250.0 2 Weeks
2.0g USD 450.0 2 Weeks
5.0g USD 650.0 2 Weeks
10.0g USD 850.0 2 Weeks
20.0g USD 1450.0 2 Weeks
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Synonym: Tioconazole; UK20,349; UK-20,349; UK 20,349; Gyno-Trosyd; Monistat 1-Day; Mykontral; Trosderm; Trosid; Trosyd; Trosyl; Vagistat.

IUPAC/Chemical Name: 1-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

InChi Key: QXHHHPZILQDDPS-UHFFFAOYSA-N

InChi Code: 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

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

Appearance: White to off-white crystalline powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 387.703 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Rosato A, Piarulli M, Schiavone BI, Montagna MT, Caggiano G, Muraglia M, Carone A, Franchini C, Corbo F. In vitro synergy testing of anidulafungin with fluconazole, tioconazole, 5-flucytosine and amphotericin B against some Candida spp. Med Chem. 2012 Jul;8(4):690-8. PubMed PMID: 22530916.

2: Grudzień M, Gajewska A, Pluciński F, Mazurek AP. Molecular properties relevant to bioavailability of tioconazole and its derivatives. Acta Pol Pharm. 2008 Nov-Dec;65(6):757-8. PubMed PMID: 19172861.

3: Grudzień M, Krakowiak N, Pluciński F, Mazurek AP. Molecular properties of oxyconazole and tioconazole as the criteria for their bioavailability estimation. Acta Pol Pharm. 2008 Jan-Feb;65(1):123-4. PubMed PMID: 18536184.

4: Sidou F, Soto P. A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers. Int J Tissue React. 2004;26(1-2):17-24. Erratum in: Int J Tissue React. 2004;26(3-4):119. PubMed PMID: 15573688.

5: Sobue S, Sekiguchi K. Difference in percutaneous absorption and intracutaneous distribution in guinea pigs among topical antifungal drugs (tioconazole solution, tioconazole cream, miconazole nitrate solution and bifonazole solution). Biol Pharm Bull. 2004 Sep;27(9):1428-32. PubMed PMID: 15340231.

6: Simonetti G, Simonetti N, Villa A. Increase of activity of tioconazole against resistant microorganisms by the addition of butylated hydroxyanisole. Int J Antimicrob Agents. 2003 Oct;22(4):439-43. PubMed PMID: 14522107.

7: Pereira M, Fachin AL, Martinez-Rossi NM. The gene that determines resistance to tioconazole and to acridine derivatives in Aspergillus nidulans may have a corresponding gene in Trichophyton rubrum. Mycopathologia. 1998;143(2):71-5. PubMed PMID: 10205888.

8: Faria A, Gonçalo S, Gonçalo M, Freitas C, Baptista PP. Allergic contact dermatitis from tioconazole. Contact Dermatitis. 1996 Oct;35(4):250-2. PubMed PMID: 8957651.

9: Heikkilä H, Stubb S, Reitamo S. A study of 72 patients with contact allergy to tioconazole. Br J Dermatol. 1996 Apr;134(4):678-80. PubMed PMID: 8733370.

10: Fachin AL, Maffei CM, Martinez-Rossi NM. In vitro susceptibility of Trichophyton rubrum isolates to griseofulvin and tioconazole. Induction and isolation of a resistant mutant to both antimycotic drugs. Mutant of Trichophyton rubrum resistant to griseofulvin and tioconazole. Mycopathologia. 1996;135(3):141-3. PubMed PMID: 9066154.

11: Penn SG, Bergström ET, Goodall DM. Capillary electrophoresis with chiral selectors: optimization of separation and determination of thermodynamic parameters for binding of tioconazole enantiomers to cyclodextrins. Anal Chem. 1994 Sep 15;66(18):2866-73. PubMed PMID: 7978295.

12: Gibson G, Buckley A, Murphy GM. Allergic contact dermatitis from tioconazole without cross-sensitivity to other imidazoles. Contact Dermatitis. 1994 May;30(5):308. PubMed PMID: 8088154.

13: Quirino AP, Barros MA. Contact dermatitis from tioconazole. Contact Dermatitis. 1994 Apr;30(4):240-1. PubMed PMID: 8033553.

14: Jones RN, Bale MJ, Hoban D, Erwin ME. In vitro antimicrobial activity of tioconazole and its concentrations in vaginal fluids following topical (vagistat-1 6.5%) application. Diagn Microbiol Infect Dis. 1993 Jul;17(1):45-51. PubMed PMID: 8359005.

15: Piletta P, Pasche-Koo F, Saurat JH. Contact dermatitis from tioconazole mimicking "one hand two feet syndrome". Contact Dermatitis. 1993 May;28(5):308. PubMed PMID: 8365142.

16: Penn SG, Goodall DM, Loran JS. Differential binding of tioconazole enantiomers to hydroxypropyl-beta-cyclodextrin studied by capillary electrophoresis. J Chromatogr. 1993 Apr 23;636(1):149-52. PubMed PMID: 8491834.

17: Marren P, Powell S. Contact sensitivity to tioconazole and other imidazoles. Contact Dermatitis. 1992 Aug;27(2):129-30. PubMed PMID: 1395626.

18: Brunelli D, Vincenzi C, Morelli R, Tosti A. Contact dermatitis from tioconazole. Contact Dermatitis. 1992 Aug;27(2):120. PubMed PMID: 1395619.

19: Onayemi O, Aldridge RD, Shaw S. Allergic contact dermatitis from tioconazole. A report of 2 cases. Contact Dermatitis. 1992 Mar;26(3):193-4. PubMed PMID: 1387058.

20: Stubb S, Heikkilä H, Reitamo S, Förström L. Contact allergy to tioconazole. Contact Dermatitis. 1992 Mar;26(3):155-8. PubMed PMID: 1387056.