chemistry

Mazindol

Mazindol 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 Mazindol rather than just read about it. In short: Mazindol, sold under the brand names Mazanor and Sanorex, is an appetite suppressant which is used in the short-term treatment of obesity. It is also used off-label in the treatment of narcolepsy and cataplexy.

Key takeaways

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

Reference excerpt

Mazindol, sold under the brand names Mazanor and Sanorex, is an appetite suppressant which is used in the short-term treatment of obesity. It is also used off-label in the treatment of narcolepsy and cataplexy. The drug is taken orally. Mazindol was developed by Sandoz-Wander in the 1960s. The US Food and Drug Administration approved mazindol in June 1973, but Novartis, the manufacturer, discontinued it in 1999 for reasons unrelated to its efficacy or safety.

Medical uses Mazindol is used in short-term (i.e., a few weeks) treatment of obesity, in combination with a regimen of weight reduction based on caloric restriction, exercise, and behavior modification in people with a body mass index greater than 30, or in those with a body mass index greater than 27 in the presence of risk factors such as hypertension, diabetes, or hyperlipidemia. Mazindol is not currently available as a commercially marketed and FDA-regulated prescription agent for the treatment of obesity. Off-label use of mazindol has demonstrated efficacy in treating symptoms of narcolepsy and cataplexy. Studies beginning in the 1970s indicated that mazindol reduced sleep attacks and cataplexy with comparable efficacy to amphetamine, but with reduced cardiovascular side effects.

Overdose Symptoms of a mazindol overdose include restlessness, tremor, rapid breathing, confusion, hallucinations, panic, aggression, nausea, vomiting, diarrhea, irregular heartbeat, and seizures.

Pharmacology

Pharmacodynamics

Mazindol is a sympathomimetic amine, which is similar to amphetamine. It stimulates the central nervous system, which increases heart rate and blood pressure, and decreases appetite. Sympathomimetic anoretics (appetite suppressants) are used in the short-term treatment of obesity. Their appetite-reducing effect tends to decrease after a few weeks of treatment. Because of this, these medicines are useful only during the first few weeks of a weight-loss program. Although the mechanism of action of the sympathomimetics in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Like other sympathomimetic appetite suppressants, mazindol is thought to act as a reuptake inhibitor of norepinephrine, dopamine, and serotonin. In addition to its other actions, mazindol has been found to act as a very-low-potency partial agonist of the orexin OX2 receptor. It showed 35% binding inhibition at the human orexin OX2 receptor at a concentration of 10,000 nM (a measure of binding affinity), an activational potency (EC50Tooltip half-maximal effective concentration) of 16,000 nM, and an activational efficacy (EmaxTooltip maximal efficacy) of approximately 25 to 50%. This action is profoundly less potent than mazindol's monoamine reuptake inhibition. Whether the orexin OX2 receptor partial agonism of mazindol occurs at clinically relevant concentrations or is pharmacologically significant is unclear.

Chemistry

Tautomers Mazindol exhibits pH dependent tautomerization between the keto form and the cyclic hemiaminal. Mazindol exists in the tricyclic (-ol) form in neutral media and undergoes protonation to the benzophenone tautomer in acidic media. QSAR studies have indicated that the ability of mazindol to inhibit NE and DA reuptake may be mediated by the protonated (benzophenone) tautomer.

Synthesis The chemical synthesis of mazindol has been described.

Related compounds Some analogues and related compounds include ciclazindol, setazindol, trazium, dazadrol, and AW-15'1129, among others.

QSAR From available QSAR data, the following trends are apparent:

Removal of the tertiary alcohol improves DAT and SERT binding without substantially reducing NET affinity. This compound has been called "mazindane". Removal of the p-chlorine atom increases NET affinity and substantially reduces DAT and SERT affinity. Expansion of the imidazoline ring to the corresponding six-membered homolog increases DAT affinity by ~10 fold. Replacement of the phenyl moiety with a naphthyl ring system results in a ~50 fold increase in SERT affinity without significant decreases in NET or DAT affinities. Halogenation of 3' and/or 4' position of the phenyl ring of mazindol results in increased potency at NET, DAT, and SERT. Fluorination of the 7' position of the tricyclic phenyl ring results in a ~2 fold increase in binding affinity to DAT.

Research Additional patented uses include for the treatment of schizophrenia, reducing cravings for cocaine, and for the treatment of neurobehavioral disorders.

Attention deficit hyperactivity disorder As of 2016 mazindol was being studied in clinical trials for attention-deficit hyperactivity disorder (ADHD). There is a Swiss study investigating its efficacy in treating attention deficit hyperactivity disorder (ADHD).

Notes

References

Illustrations

Worked examples

Example 1 — a first encounter with Mazindol

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

In research: Mazindol 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 Mazindol 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: Mazindol is common in secondary-school and first-year university syllabi. It links to neighbouring topics 4-Chlorophenyl compounds, Imidazolines, Serotonin–norepinephrine–dopamine reuptake inhibitors, so understanding it makes those chapters shorter.
In everyday life: Look for Mazindol 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 Mazindol in 20 minutes

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

Frequently asked questions

What is Mazindol in simple terms?

Why does Mazindol 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 Mazindol?

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 Mazindol.