science

Naproxcinod

Naproxcinod is a science 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 Naproxcinod rather than just read about it. In short: Naproxcinod (nitronaproxen) is a nonsteroidal anti-inflammatory drug (NSAID) developed by the French pharmaceutical company NicOx. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide (NO) donor.

Key takeaways

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

Reference excerpt

Naproxcinod (nitronaproxen) is a nonsteroidal anti-inflammatory drug (NSAID) developed by the French pharmaceutical company NicOx. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide (NO) donor. This second mechanism of action makes naproxcinod the first in a new class of drugs, the cyclooxygenase inhibiting nitric oxide donators (CINODs), that are hoped to produce similar analgesic efficacy to traditional NSAIDs, but with less gastrointestinal and cardiovascular side effects. In December 2006, Scientific American distinguished naproxcinod as one of the ten most promising treatments for the world's biggest health threats. However, in 2010 the U.S. Food and Drug Administration determined that further clinical trials would be needed to obtain approval.

Current situation in pain treatment There are people who are currently relying on traditional NSAIDs and COX-2 inhibitors (for example celecoxib) to treat chronic pain and inflammation. COX-2 inhibitors have been associated with an increased risk of serious cardiovascular events such as strokes or heart attacks. Therefore, there is a need for safer medications. This need is particularly acute among patients with high cardiovascular risk like hypertension which represents 50% of osteoarthritis sufferers.

Proposed indications Three phase III clinical trials led by NicOx have shown that naproxcinod was effective to treat pain against knee osteoarthritis and hip osteoarthritis. A phase II study showed no significant differences in efficacy between naproxcinod and the COX-2 inhibitor rofecoxib in the treatment of pain. In osteoarthritis, a 750 mg dose is equipotent to 500 mg of naproxen for the treatment of inflammation but with the added benefit of attenuating the cardiovascular effects traditionally associated with NSAIDs. In July 2010 the FDA decided not to approve naproxcinod.

Mechanism of action Naproxcinoid is metabolized to naproxen and a nitric oxide donating moiety. NO has various cardiovascular effects, including vasodilatory and platelet-inhibitory actions as well as the inhibition of vascular smooth muscle proliferation that serves to maintain normal vascular tone.

Safety profile

Blood pressure profile According to some experts, cardiovascular risks induced by COX-2 inhibitors are caused by increases in blood pressure. Naproxcinod demonstrated in a clinical trial with 916 patients to have a blood pressure profile similar to placebo. Two phase II randomized controlled trials have shown a decreased systolic blood pressure by 2.1 mmHg after patients took naproxcinod (375 mg or 750 mg twice daily) for six weeks. These effects were especially pronounced in hypertensive populations.

Clinical relevance of small increase in blood pressure During a U.S. Food and Drug Administration (FDA) COX-2 advisory committee meeting, doctors have underlined the important role of small increase in blood pressure. They cited the CAMELOT trial which has concluded that even a small decrease in systolic blood pressure of 5 mmHg could lead to a reduction of 31% in cardiovascular events. Clinical studies about rofecoxib have shown that this drug increases the systolic blood pressure. A 2005 analysis shows that a blood pressure decrease of 3.1 mmHG could avoid over 30,000 deaths from stroke and 2,000 deaths from coronary disease, resulting in more than 449,000 person years of life saved and 1.4 billion US$ in direct health care cost savings.

Gastrointestinal safety NSAIDs have also been associated with gastrointestinal risks such as bleedings. Early studies demonstrated that naproxcinod had a better gastrointestinal profile than naproxen, especially for the gastroduodenal mucosa, but a 2009 review has found only a slight and possibly not clinically relevant reduction of gastrointestinal side-effects.

Commercialization Naproxcinod completed a phase III study needed for a New Drug Application (NDA). As a result, Nicox submitted its project to the FDA in September 2009. In July 2010, the FDA decided not to approve naproxcinod without further clinical trials. Nicox submitted a Marketing Authorization Application (MAA) to the European Medicines Agency (EMEA) in December 2009. Nicox and Fera Pharmaceuticals announced in November 2015 that they had entered into a license agreement for the development and commercialization of naproxcinod in the United States.

See also Nitrosoprodenafil – a dual PDE5 inhibitor / NO donor

References

Worked examples

Example 1 — a first encounter with Naproxcinod

Start with the simplest possible case. Write down what Naproxcinod claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, 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 Naproxcinod 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 Naproxcinod 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 Naproxcinod

In research: Naproxcinod appears in science 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 Naproxcinod 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: Naproxcinod is common in secondary-school and first-year university syllabi. It links to neighbouring topics Carboxylate esters, Naphthol ethers, Nitrate esters, so understanding it makes those chapters shorter.
In everyday life: Look for Naproxcinod 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 Naproxcinod in 20 minutes

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

Frequently asked questions

What is Naproxcinod in simple terms?

Why does Naproxcinod matter?

Because it connects several science 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 Naproxcinod?

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 Naproxcinod.