chemistry

Zanoterone

Zanoterone 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 Zanoterone rather than just read about it. In short: Zanoterone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (former developmental code name WIN-49596), also known as (5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol, is a steroidal antiandrogen which was never marketed. It was investigated for the treatment of benign prostatic hyperplasia (BPH) but failed to demonstrate sufficient efficacy in phase II clinica…

Key takeaways

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

Reference excerpt

Zanoterone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (former developmental code name WIN-49596), also known as (5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol, is a steroidal antiandrogen which was never marketed. It was investigated for the treatment of benign prostatic hyperplasia (BPH) but failed to demonstrate sufficient efficacy in phase II clinical trials, and also showed an unacceptable incidence rate and severity of side effects (e.g., breast pain and gynecomastia). As such, it was not further developed. Zanoterone was derived from 5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone). It is an antagonist of the androgen receptor (Ki = 2.2 μM; RBATooltip relative binding affinity compared to metribolone = 2.2%), and with the exception of antiprogestogenic activity in rat and rabbit models, is devoid of other hormonal activities. Zanoterone does not inhibit 5α-reductase, aromatase, or 3α- or 3β-hydroxysteroid dehydrogenase in vitro. The drug significantly increases testosterone and estradiol levels in men. Zanoterone has been found to not significantly inhibit mating performance or fertility in adult male rats at high dosages for an extended period of time. It has been found to act as an inducer of the enzyme CYP3A4 in vivo in rats.

Chemistry

Synthesis The chemical synthesis of zanoterone has been described.

The Ethynylation of the keto group in Epiandrosterone [481-29-8] (1). with lithium acetylide and oxidation of the 3 hydroxy group with chromium trioxide gives 17-Ethinyl-dihydrotestosterone [13611-97-7] (2). Hydroxymethylation occurs at the C2 position upon reaction with methyl formate [107-31-3] in the presence of sodium methoxide to give PC173399331 (3). The enol alcohol is then converted to its benzoate protecting group, PC53632489 (4) and reaction give Mesylhydrazide [10393-86-9] gives the pyrazole ring (5). The benzoate group was required since reacting 3 directly with the hydrazine affords mixtures of the 2 possible regioisomers.

See also List of steroidal antiandrogens

References

Illustrations

Worked examples

Example 1 — a first encounter with Zanoterone

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

In research: Zanoterone 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 Zanoterone 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: Zanoterone is common in secondary-school and first-year university syllabi. It links to neighbouring topics Abandoned drugs, Androstanes, Antiprogestogens, so understanding it makes those chapters shorter.
In everyday life: Look for Zanoterone 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 Zanoterone in 20 minutes

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

Frequently asked questions

What is Zanoterone in simple terms?

Why does Zanoterone 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 Zanoterone?

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 Zanoterone.