Tioconazole

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Cat Number

API65899732

CAS Number

65899-73-2

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CAS Number

65899-73-2

EINECS

265-973-8

Storage

Room temperature

Synonyms

1-(2-((2-chloro-3-thienyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazol;vagistat

Molecular Formula

C16H13Cl3N2OS

Molecular Weight

387.7

Smiles

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

Appearance

White to off-white solid

Melting Point

79-81℃

Boiling Point

534.5℃

Relative Density

1.3

pKa

6.66

General Description

Tioconazole is a broad-spectrum imidazole antifungal with activity against dermatophytes, yeasts (including Candida species), Gram-positive bacteria, and certain protozoa (Trichomonas vaginalis). Its chemical structure features a thiazole ring rather than the imidazole ring found in most azole antifungals, which contributes to its broader spectrum of activity. The thiazole ring substitution imparts greater lipophilicity and enhanced keratin-binding properties.

Mechanism of Action

Tioconazole inhibits lanosterol 14-alpha-demethylase (CYP51) in the fungal ergosterol biosynthesis pathway, reducing ergosterol production and disrupting fungal cell membrane integrity. Its imidazole/thiazole heterocyclic system coordinates with the heme iron of CYP51, blocking the demethylation step. Additionally, tioconazole exerts antibacterial effects against Gram-positive organisms by disrupting bacterial cell membrane function, and demonstrates antiprotozoal activity against Trichomonas vaginalis.

Application

Tioconazole is indicated for the topical treatment of tinea pedis (athlete's foot), tinea cruris (jock itch), tinea corporis (ringworm), and cutaneous candidiasis.

Tioconazole, an FDA-approved antifungal drug, was identified as an ATG4 inhibitor through a drug repurposing screen integrating computational docking, molecular dynamics simulations, and biochemical/cellular assays. Tioconazole inhibited ATG4A and ATG4B with IC50 values of 1.3 μM and 1.8 μM, respectively, by occupying the active site of ATG4 in its open form. It reduced autophagic flux in cancer cells, as evidenced by accumulation of LC3-II and autophagosomes, and impaired autophagosome-lysosome fusion.
Tioconazole sensitized cancer cells to starvation and chemotherapeutic agents (doxorubicin, camptothecin) in colorectal cancer HCT116, glioblastoma H4, and breast cancer MDA-MB-231 cells, increasing apoptosis and reducing cell viability. In HCT116 xenograft mouse models, tioconazole (60 mg/kg) combined with doxorubicin reduced tumor volume and weight, increased LC3 puncta and cleaved caspase-3 in tumor tissues. Tioconazole represents a potential anticancer agent or chemosensitizer through ATG4 inhibition and autophagy suppression.

Fig. 1 Docking and MD Simulations for Tioconazole Binding to ATG4. (Liu P F.; et al. 2018)

References

Liu P F, et al. Drug repurposing screening identifies tioconazole as an ATG4 inhibitor that suppresses autophagy and sensitizes cancer cells to chemotherapy. Theranostics, 2018, 8(3): 830.

Tioconazole-loaded transferosomes (TTFs) were formulated using a thin lipid film hydration method and optimized via a factorial design. The optimized batch (B4) contained 50 mg Phospholipon®90H and 45 mg sodium deoxycholate, achieving vesicle size 171.4 nm, PDI 0.36, entrapment efficiency 93.89%, and zeta potential -20.73 mV. TTFs were incorporated into Carbopol 934/sodium CMC hydrogel. The F2 batch (1.5% sodium CMC) showed 94.23% drug release over 24 hours with flux 47.23 μg/cm²/h, following Higuchi kinetics with non-Fickian diffusion. In a DNCB-induced atopic dermatitis rat model, low-dose TTFsH (12.5 mg tioconazole) significantly reduced erythema and scratching scores compared to marketed Candiderm cream. Histopathology confirmed recovered dermis and epidermis with reduced inflammatory cell infiltration. TTFsH enhanced skin penetration through the deformable nature of transferosomes, generating osmotic gradients that disrupt stratum corneum lipids. Low-dose TTFsH demonstrated superior efficacy to high dose, offering a promising topical treatment for atopic dermatitis.

Fig. 1 Docking and MD Simulations for Tioconazole Binding to ATG4. (Kharwade R.; et al. 2023)

References

Kharwade R, et al. DOE-assisted formulation, optimization, and characterization of tioconazole-loaded transferosomal hydrogel for the effective treatment of atopic dermatitis: in vitro and in vivo evaluation. Gels, 2023, 9(4): 303.

What is the recommended storage condition for Tioconazole?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

What documentation is provided with each batch of Tioconazole?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

What is the minimum order quantity (MOQ) for Tioconazole?

Flexible MOQ options are available to support both early-stage research and large-scale manufacturing needs. Our team can tailor order quantities to match your specific requirements.

Does Tioconazole have pharmacopoeial monograph compliance?

Material meeting applicable pharmacopoeial specifications or equivalent internal quality standards can be supplied; please contact us with your specific compendial requirements.

Is Tioconazole manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.