chemistry

Terconazole

Terconazole is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Terconazole rather than just read about it. In short: Terconazole is an antifungal drug used to treat vaginal yeast infection. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell.

Key takeaways

Terconazole belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Terconazole to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Terconazole from memory before moving on to harder problems.

Reference excerpt

Terconazole is an antifungal drug used to treat vaginal yeast infection. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell. It has a relatively broad spectrum compared to azole compounds but not triazole compounds. Testing shows that it is a suitable compound for prophylaxis for those that suffer from chronic vulvovaginal candidiasis.

Medical uses Terconazole is approved to treat vulvovaginal candidiasis (vaginal thrush). It works as a broad spectrum antifungal and has shown to be an effective first-line treatment against other Candida species. It also shows effectiveness against dermatomycoses in animal models. A review found that short-term rates for intravaginally administered azole treatments shows cure in 80% of cases in a short term follow-up and 66% over long term follow-up. In a double-blind study by Slavin in 1992, terconazole showed a 75% mycological cure over a short-term period (7–14 days) and 100% mycological cure over a long-term period (28–34 days). This study focused on the drug as an 80 mg vaginal suppository, taken three times overnight by 10 women. In another placebo-controlled, double blind study by Schmidt et al., the efficacy of different concentrations of terconazole creams were tested. Cream was applied for three days to 24 women between the ages of 18 and 60. The results showed 0.8% terconazole mycologic cure rates were 83.3% within 1–3 days of starting treatment, 83.3% within 8–11 days of treatment and 58.3% within 30–35 days of treatment. The suppository is more effective after a long-term follow-up than terconazole as a cream or other intravaginal treatments.

Side effects The most common side effects of terconazole include headaches, vulvar/vaginal irritation, rash, itching, burning or discomfort. Other side effects may include abdominal pain or cramps, dysmenorrhea, chills, fever and allergic reactions. Flu-like symptoms have been recorded in those that take suppositories greater than 160 mg. May cause birth defects if used in the first trimester. Terconazole is not considered hazardous when handled under normal conditions. It is generally non-flammable and non-carcinogenic. Generally is non-toxic, however, can emit toxic fumes when dust is set alight. Can cause respiratory distress as dust. Can be absorbed by embryo within the first trimester of pregnancy and cause birth defects. Cross inhibition shows that there may be some toxicity.

Interactions Terconazole may interact with the spermicide nonoxynol-9. A precipitate is formed upon combination of both drugs. Terconazole may weaken latex-based condoms.

Chemistry Terconazole is a triazole ketal with broad-spectrum antifungal/antimycotic tendencies. Terconazole synthesis synologous with ketoconazole except for the fact that triazole and not imidazole heterocyclic ring is used, and that isopropyl group instead of acetamide.

Terconazole has the chemical formula C26H31Cl2N5O3. The chemical name for terconazole is 1-{[(2S,4S)-2-(2,4-dichlorophenyl)-4-{[p-(4-isopropyl-1-piperazinyl)phenoxy]methyl}-1,3-dioxolan-2-yl]methyl}-1H-1,2,4-triazole. Terconazole has a melting point of 126.3 °C (259.34 °F). The molecular weight of terconazole is 532.462 g/mol. Terconazole is synthesized using two chemical compounds: cis-[2(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl] methyl benzoate and the sodium salt of triazole, created by mixing triazole with sodium hydride. These are put in a solution and catalyzed using dimethyl sulfate at 1300 °C (2372 °F) to give many different types of triazole derivatives. These are purified using alcohol and chromatography. Terconazole is non-reactive except when exposed to strong oxidizing agents or strong bases due to the nitrogen attached to the triazole ring. It has been found to be photosensitive.

Mechanism of action Terconazole binds to the heme iron component on the cytochrome P450 enzyme lanosterol of fungi, also known as CYP3A4. The gene ERG11 controls lanosterol creation. Lanosterol is found within the yeast plasma membrane. It is a class of methylsterol. Within a normal yeast cell, lanosterol is demethylated using 14α-demethylation. This process creates zymosterol: a major constituent in the ergosterol biosynthesis pathway for the creation of cell membrane constituents in yeast. This structure provides the membrane with fluidity. This occurs by transforming lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-β-ol. This stops respiration by prohibiting reduction of NADH to NAD. This stops biosynthesis of cell membrane products as well as transport and catabolism. Eventually, membrane fluidity and activity of membrane bound enzymes become depleted. It has also been shown to inhibit morphologic change of yeast as well as cell adherence and is directly toxic to yeast. Terconazole targets fungi specifically since humans do not use lanosterol in this pathway. This process does not affect all fungi such as Pneumocystis jirovecii, which lacks lanosterol.

Metabolism Absorption of terconazole is 5–8% in patients that have had a hysterectomy and 12–16% in other patients. In those that administered 0.8% terconazole, plasma concentrations of the drug remained quite low with the peak plasma concentration being 0.006 mcg at 6.6 hours. Those metabolism rates show similar results in pregnant vulvovaginal candidiasis, non-pregnant vulvovaginal candidiasis and healthy women. The half-life of terconazole in blood is recorded to be around 6.9 hours over a range of 4–11.3 hours). Radioactivity of plasma terconazole is low compared to terconazole at 0.6%. Excretion of radioactivity is via two routes, renal (32–53%) and fecal (47–52%). Metabolism is extensive and is highly protein bound (94.9%) with the degree of binding being independent of drug concentration.

… excerpt ends here. Continue reading the full article.

Illustrations

Worked examples

Example 1 — a first encounter with Terconazole

Start with the simplest possible case. Write down what Terconazole claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Terconazole before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Terconazole ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Terconazole

In research: Terconazole appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Terconazole in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Terconazole is common in secondary-school and first-year university syllabi. It links to neighbouring topics Dichlorophenyl compounds, Dioxolanes, Isopropyl compounds, so understanding it makes those chapters shorter.
In everyday life: Look for Terconazole outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Terconazole in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Terconazole means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Terconazole out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Terconazole in simple terms?

Terconazole is an antifungal drug used to treat vaginal yeast infection. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell.

Why does Terconazole matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Terconazole?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Terconazole.