Terconazole

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Cat Number

API0232232

CAS Number

67915-31-5

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CAS Number

67915-31-5

EINECS

267-751-6

Storage

Store at room temperature

Synonyms

Terazol 7; Triaconazole; Terazol; Gyno-Terazol; Terazol 3; Fungistat; Panlomyc; Terconazolum

Molecular Formula

C26H31Cl2N5O3

Molecular Weight

532.5

Smiles

CC(C)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl

Appearance

White to off-white solid powder

Melting Point

126.3°C

Boiling Point

681.8±65.0°C at 760 mmHg (Predicted)

Relative Density

1.35±0.1 (Predicted)

General Description

Terconazole is a synthetic triazole antifungal agent with a piperazine ring and a dichlorophenyl group, structurally related to ketoconazole. Its chemical structure is 1-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-propan-2-ylpiperazine.

Mechanism of Action

Terconazole inhibits the synthesis of ergosterol, a critical component of the fungal cell membrane, by inhibiting the cytochrome P450 enzyme lanosterol 14α-demethylase. This blocks the conversion of lanosterol to ergosterol, leading to the accumulation of toxic sterols and disruption of membrane integrity. The drug is fungistatic against Candida species, including Candida albicans, Candida tropicalis, and Candida glabrata.

Application

Terconazole is indicated for the topical treatment of vulvovaginal candidiasis (yeast infection). It is effective against both acute and recurrent infections and is available in cream and suppository formulations. The drug is also effective against Candida species that are resistant to other azoles.

A MEPS-HPLC-DAD method was developed for simultaneous determination of 12 azole drugs (bifonazole, clotrimazole, itraconazole, miconazole, etc.) in human plasma and urine. Separation took 36 min, validation ranges were 0.02–5 µg/mL (ravuconazole), 0.2–5 µg/mL (terconazole), and 0.05–5 µg/mL for others. The method met International Guidelines for precision and trueness and was successfully applied to real samples after oral administration of itraconazole and miconazole.

Fig. 1 Effects of cycles number on process efficiency for the different analytes during sample loading and sample elution. (Campestre C, et al., 2017)

References

Campestre C, et al. Analysis of imidazoles and triazoles in biological samples after MicroExtraction by packed sorbent. J Enzyme Inhib Med Chem. 2017;32(1):1-11.

Terconazole-loaded lecithin-integrated liquid crystalline nano-organogels (LCGs) were developed for dermal delivery. The optimized LCG showed promising physicochemical properties and significantly enhanced skin permeation (4.7-fold ex vivo, 2.7-fold in vivo) compared to conventional hydrogel. Acute irritation studies confirmed skin safety, and in vivo antifungal activity demonstrated superiority over conventional hydrogel for treating Candida infection. Lecithin-based LCGs are promising dermal nanocarriers for skin targeting.

Fig. 2 Ternary phase diagram of the selected system components (lecithin/capryol 90/water) in weight percentage showing area of LCG. (Elnaggar YS, et al., 2016)

References

Elnaggar YS, et al. Novel lecithin-integrated liquid crystalline nanogels for enhanced cutaneous targeting of terconazole: development, in vitro and in vivo studies. Int J Nanomedicine. 2016;11:5531-5547.

Does Terconazole require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation of the triazole and piperazine rings. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Terconazole?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate degradation.

Is Terconazole stable in topical cream and suppository formulations?

Yes, when formulated with preservatives and protected from light.

How is the impurity terconazole N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.