chemistry

Miconazole

Miconazole 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 Miconazole rather than just read about it. In short: Miconazole, sold under the brand name Monistat among others, is an antifungal medication used to treat ring worm, pityriasis versicolor, and yeast infections of the skin or vagina. It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot).

Key takeaways

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

Reference excerpt

Miconazole, sold under the brand name Monistat among others, is an antifungal medication used to treat ring worm, pityriasis versicolor, and yeast infections of the skin or vagina. It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot). It is applied to the skin or vagina as a cream or ointment. Common side effects include itchiness or irritation of the area in which it was applied. Use in pregnancy is believed to be safe for the baby. Miconazole is in the imidazole family of medications. It works by decreasing the ability of fungi to make ergosterol, an important part of their cell membrane. Miconazole was patented in 1968 and approved for medical use in 1971. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.

Medical uses Miconazole is used externally for the treatment of ringworm, jock itch, and athlete's foot. Internal application is used for oral candidiasis or vaginal thrush (yeast infection).

Side effects Miconazole is generally well tolerated. The oral gel can cause dry mouth, nausea and an unpleasant taste in about 1–10% of people. Anaphylactic reactions are rare. The drug prolongs the QT interval.

Interactions Miconazole is partly absorbed in the intestinal tract when used orally, as with the oral gel, and possibly when used vaginally. This can lead to increased concentrations of drugs that are metabolized by the liver enzymes CYP3A4 and CYP2C9, because miconazole inhibits these enzymes. Such interactions occur for example with anticoagulants of the warfarin type, phenytoin, some newer atypical antipsychotics, ciclosporin, and most statins used to treat hypercholesterolemia. These interactions are not relevant for miconazole that is applied to the skin.

Contraindications Miconazole is contraindicated for people who use certain drugs that are metabolized by CYP3A4, for the reasons mentioned above:

drugs that also prolong the QT interval because of potential problems with the heart rhythm ergot alkaloids statins triazolam and oral midazolam sulfonamides with a potential to cause hypoglycaemia (low blood sugar)

Pharmacology

Mechanism of action Miconazole inhibits the fungal enzyme 14α-sterol demethylase, resulting in a reduced production of ergosterol. In addition to its antifungal actions, miconazole, similarly to ketoconazole, is known to act as an antagonist of the glucocorticoid receptor. Miconazole is also known to bind to tubulin and inhibit its polymerization. Miconazole inhibits CYP2J2.

Pharmacokinetics After application to the skin, miconazole can be measured in the skin for up to four days, but less than 1% is absorbed into the bloodstream. When applied to the oral mucosa (and possibly also for vaginal use), it is significantly absorbed. In the bloodstream, 88.2% are bound to plasma proteins and 10.6% to blood cells. The substance is partly metabolized via the liver enzyme CYP3A4 and mainly eliminated via the faeces.

Chemistry The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid. Miconazole crystallises as colourless prisms in the monoclinic space group P21/c.

Other uses Miconazole is also used in Ektachrome film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde. Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.

Brands and formulations

Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh): In 2010, the US Food and Drug Administration approved Oravig (miconazole) buccal tablets for the local treatment of oropharyngeal candidiasis, more commonly known as thrush, in adults and children age 16 and older. External skin treatment (brand names Desenex and Zeasorb in US and Canada; Micatin, Monistat-Derm, Daktarin in India, UK, Australia, Belgium and the Philippines; Kalpanax in Indonesia; Daktar in Norway; Fungidal in Bangladesh; Decocort in Malaysia) (Note that Desenex originally contained not miconazole, but rather the fungistatic agents, undecylenic acid and zinc undecylenate, which were in the foot powder developed by the US government for troops during WWII.) Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):

In Japan, Mochida Healthcare, a subsidiary of Mochida Pharmaceutical, produces a line of body soaps and shampoo under the brand name Collage (コラージュ) that contain miconazole nitrate as their main ingredient.

References

Illustrations

Worked examples

Example 1 — a first encounter with Miconazole

Start with the simplest possible case. Write down what Miconazole 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 Miconazole 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 Miconazole 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 Miconazole

In research: Miconazole 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 Miconazole 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: Miconazole is common in secondary-school and first-year university syllabi. It links to neighbouring topics 21-Hydroxylase inhibitors, Antiglucocorticoids, Aromatase inhibitors, so understanding it makes those chapters shorter.
In everyday life: Look for Miconazole 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 Miconazole in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Miconazole 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 Miconazole out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Miconazole in simple terms?

Why does Miconazole 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 Miconazole?

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 Miconazole.