chemistry

Mitotane

Mitotane 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 Mitotane rather than just read about it. In short: Mitotane, sold under the brand name Lysodren, is a steroidogenesis inhibitor and cytostatic antineoplastic medication which is used in the treatment of adrenocortical carcinoma and Cushing's syndrome. It is a derivative of the early insecticide DDT and an isomer of p,p'-DDDTooltip dichlorodiphenyldichloroethane (4,4'-dichlorodiphenyldichloroethane) and is also known as 2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p…

Key takeaways

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

Reference excerpt

Mitotane, sold under the brand name Lysodren, is a steroidogenesis inhibitor and cytostatic antineoplastic medication which is used in the treatment of adrenocortical carcinoma and Cushing's syndrome. It is a derivative of the early insecticide DDT and an isomer of p,p'-DDDTooltip dichlorodiphenyldichloroethane (4,4'-dichlorodiphenyldichloroethane) and is also known as 2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD).

Medical uses Mitotane has been produced by Bristol Myers Squibb but it is marketed as an orphan drug for adrenocortical carcinoma due to the small number of patients in need of it. Its main use is in those patients who have persistent disease despite surgical resection, those who are not surgical candidates, or those who have metastatic disease. In a 2007 retrospective study of 177 patients from 1985 to 2005 showed a significant increase in the recurrence-free interval after radical surgery followed by mitotane when compared to surgery alone. The drug is also sometimes used in the treatment of Cushing's syndrome. Therapy with mitotane is initiated using an escalating regimen. The extent or intensity of the therapy is gradually increased. This depends on how well the individual patient tolerates the drug and the extent to which it affects the patient's performance status (according to the ECOG/Karnofsky Performance Status). Monitoring of the mitotane concentration in the blood is recommended. The general target value is 14-20 mg/L. Mitotane therapy is initiated using an escalating regimen. In all patients receiving mitotane therapy, glucocorticoid replacement is recommended, except for patients with persistent cortisol excess. In these cases, at least twice the standard replacement dose is generally required. This is due to the increased steroid excretion and the rise in cortisol-binding globulin. Mitotane-induced side effects must be monitored regularly and treated appropriately, avoiding over-, under-, or inappropriate treatment. Furthermore, initiating supportive therapy is advisable to improve mitotane tolerance. Ideally, this should be done before severe toxicity develops. Mitotane causes significant drug interactions due to strong induction of CYP3A4. Therefore, it is crucial to check all concomitant medications for CYP3A4 interactions and replace them with an alternative if necessary and available. Other healthcare providers should be advised not to initiate any other drug therapies without prior consultation.

Side effects The use of mitotane is unfortunately limited by side effects, which, as reported by Schteingart et al., include anorexia and nausea (88%), diarrhea (38%), vomiting (23%), decreased memory and ability to concentrate (50%), rash (23%), gynecomastia (50%), arthralgia (19%), and leukopenia (7%).

Pharmacology

Pharmacodynamics Mitotane is an inhibitor of the adrenal cortex. It acts as an inhibitor of cholesterol side-chain cleavage enzyme (P450scc, CYP11A1), and also of 11β-hydroxylase (CYP11B1), 18-hydroxylase (aldosterone synthase, CYP11B2), and 3β-hydroxysteroid dehydrogenase (3β-HSD) to a lesser extent. In addition, mitotane has direct and selective cytotoxic effects on the adrenal cortex, via an unknown mechanism, and thereby induces permanent adrenal atrophy similarly to DDD. Mitotane has also been reported to interact with tubulin and inhibit its polymerization.

Chemistry Analogues of mitotane include aminoglutethimide, amphenone B, and metyrapone.

History Mitotane was introduced in 1960 for the treatment of adrenocortical carcinoma.

Society and culture

Generic names Mitotane is the generic name of the medication and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name, and JANTooltip Japanese Accepted Name.

Brand names Mitotane is sold under the brand name Lysodren.

Veterinary use Mitotane is also used to treat Cushing's disease (pituitary-dependent Cushing's syndrome) in dogs. The medication is used in the controlled destruction of adrenal tissue, leading to a decrease in cortisol production.

References

Illustrations

Worked examples

Example 1 — a first encounter with Mitotane

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

In research: Mitotane 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 Mitotane 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: Mitotane is common in secondary-school and first-year university syllabi. It links to neighbouring topics 11β-Hydroxylase inhibitors, 2-Chlorophenyl compounds, 3β-Hydroxysteroid dehydrogenase inhibitors, so understanding it makes those chapters shorter.
In everyday life: Look for Mitotane 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 Mitotane in 20 minutes

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

Frequently asked questions

What is Mitotane in simple terms?

Why does Mitotane 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 Mitotane?

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 Mitotane.