An imidazole antifungal
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Tioconazole

Item No. 26069

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
CAS Number
65899-73-2
Synonyms
  • (±)-Tioconazole
Molecular Formula
C16H13Cl3N2OS
Formula Weight
387.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 33 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
221 nm
SMILES
ClC1=CC(Cl)=C(C(CN2C=CN=C2)OCC3=C(Cl)SC=C3)C=C1
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
InChi Key
QXHHHPZILQDDPS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Tioconazole is an imidazole antifungal that inhibits the growth of various fungi, including C. albicans, C. neoformans, A. fumigatus, and T. rubrum (MICs = 4.7, 0.1, 5.7, and 0.5 µg/ml, respectively).1,2 It inhibits C-14 demethylation of sterols in a cell-free C. albicans homogenate (IC50 = 50-80 nM).3 Tioconazole (2% w/v cream) reduces the number of viable Candida cells recovered from the vagina in a mouse model of vaginal candidiasis.4 Formulations containing tioconazole have been used in the treatment of vaginal yeast infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fromtling, R.A. Overview of medically important antifungal azole derivatives. Clin. Microbiol. Rev. 1(2), 187-217 (1988).

    2. Jevons, S., Gymer, G.E., Brammer, K.W., et al. Antifungal activity of tioconazole (UK-20,349), a new imidazole derivative. Antimicrob. Agents Chemother. 15(4), 597-602 (1979).

    3. Marriott, M.S. Inhibition of sterol biosynthesis in Candida albicans by imidazole-containing antifungals. J. Gen. Microbiol. 117(1), 253-255 (1980).

    4. Marriott, M.S., Brammer, K.W., Faccini, J., et al. Tioconazole, a new broad-spectrum antifungal agent: Preclinical studies related to vaginal candidiasis. Gynakol. Rundsch 23(Suppl 1), 1-11 (1983).