chemistry

Repaglinide

Repaglinide 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 Repaglinide rather than just read about it. In short: Repaglinide is an antidiabetic drug in the class of medications known as meglitinides, and was invented in 1983. Repaglinide is a medication used in addition to diet and exercise for blood sugar control in type 2 diabetes.

Key takeaways

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

Reference excerpt

Repaglinide is an antidiabetic drug in the class of medications known as meglitinides, and was invented in 1983. Repaglinide is a medication used in addition to diet and exercise for blood sugar control in type 2 diabetes. The mechanism of action of repaglinide involves promoting insulin release from β-islet cells of the pancreas; like other antidiabetic drugs, a main side effect concern is hypoglycemia. It is sold by Novo Nordisk under the name of Prandin in the United States, Gluconorm in Canada, Surepost in Japan, Repaglinide in Egypt, and Novonorm elsewhere. In Japan it is produced by Dainippon Sumitomo Pharma.

Medical uses Repaglinide is an oral medication used in addition to diet and exercise for blood sugar control in type 2 diabetes.

Contraindications Repaglinide is contraindicated in people with:

Diabetic ketoacidosis, with or without coma Type 1 diabetes Co-administration with gemfibrozil Known hypersensitivity to drug or inactive ingredients

Adverse events Common adverse events include: Metabolic

Hypoglycemia (31%) Respiratory

Upper respiratory infection (16%) Sinusitis (6%) Rhinitis (3%) Gastrointestinal

Nausea (5%) Diarrhea (5%) Constipation (3%) Vomiting (3%) Musculoskeletal

Arthralgia (6%) Back Pain (5%) Other

Headache (11%) Paresthesia (3%) Serious adverse events include:

Cardiac ischemia (2%) Angina (1.8%) Deaths due to cardiovascular events (0.5%)

Special populations Pregnancy category C: safety in pregnant women has not been established. Data is limited, and there is only one case report that notes no complications with the use of repaglinide during pregnancy. Caution should be taken in people with liver disease and decreased kidney function when using this medication.

Drug interactions Repaglinide is a major substrate of CYP3A4 and should not be administered concomitantly with gemfibrozil, clarithromycin or azole antifungals such as itraconazole or ketoconazole. Administration of both repaglinide and one or more of these drugs results in an increase in plasma concentration of repaglinide and may lead to hypoglycemia. Co-administration of repaglinide and clopidogrel (a CYP2C8 inhibitor) may lead to a significant decrease in blood glucose levels due to a drug-drug interaction. In fact, using these drugs together for even one day can cause repaglinide levels to increase over 5-fold...and may lead to significant hypoglycemia. Repaglinide should not be combined with sulfonylurea, because they have the same mechanism of action.

Pharmacology

Mechanism of action Repaglinide lowers blood glucose by stimulating the release of insulin from the beta islet cells of the pancreas. It achieves this by closing ATP-dependent potassium channels in the membrane of the beta cells. This depolarizes the beta cells, opening the cells' calcium channels, and the resulting calcium influx induces insulin secretion.

Pharmacokinetics Absorption: repaglinide has a 56% bioavailability when absorbed from the gastrointestinal tract. Bioavailability is reduced when taken with food; the maximum concentration decreases by 20%. Distribution: The protein binding of repalglinide to albumin is greater than 98%. Metabolism: repaglinide is primarily metabolized by the liver - specifically CYP450 2C8 and 3A4 - and to a lesser extent via glucuronidation. Metabolites of repaglinide are inactive and do not display glucose-lowering effects. Excretion: repaglinide is 90% excreted in the feces and 8% in the urine. 0.1% is cleared unchanged in the urine. Less than 2% is unchanged in the feces.

History Precursor drugs to repaglinide were invented in late 1983 by scientists at Dr Karl Thomae GmbH, a German drug manufacturer located at Biberach an der Riß in southern Germany which was acquired by Boehringer Ingelheim in 1990. The drug that became repaglinide was later licensed by Boehringer to Novo Nordisk, which filed an Investigational New Drug application for the compound with the Food and Drug Administration (FDA) in April 1992. Novo Nordisk filed its New Drug Application (NDA) for Prandin in July 1997 and it was quickly approved, gaining FDA approval in December 1997. The drug was the first of the meglitinide class. It was branded Prandin because its quick onset and short duration of action concentrates its effect around meal time (the prandium was the Roman meal which is comparable to the modern lunch).

Intellectual property After several attempts to file for U.S. patent protection, a filing was made in March 1990 which eventually became U.S. Patents 5,216,167 (June 1993), 5,312,924 (May 1994) and 6,143,769 (November 2000). After filing its NDA for repaglinide in 1997, Novo Nordisk applied for patent extension under the Hatch-Waxman Act. This process, called patent term restoration, allows drug patents to be extended based on the time that a drug spent in clinical trials and in the approval process. Previously it had been decided by the U.S. Patent and Trademark Office that the expiration date of U.S. Patents 5,216,167 and 5,312,924 would be 5 September 2006. In February 2001 Prandin's patent life was extended to 14 March 2009 in response to Novo Nordisk's patent term restoration application, with U.S. Patent 5,216,167 having been reissued as RE37035. Prior to the end of repaglinide's patent term, Novo Nordisk obtained a new patent, U.S. Patent 6,677,358 (January 2004), covering the combination therapy of repaglinide together with the generic anti-diabetic drug metformin. This new patent was due to expire June 2018. In January 2011, a federal court ruled Novo Nordisk's new patent invalid on the grounds of obviousness, and unenforceable on the grounds of inequitable conduct on the part of Novo Nordisk's patent attorneys.

References

External links "Repaglinide". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on January 23, 2017.

Illustrations

Worked examples

Example 1 — a first encounter with Repaglinide

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

In research: Repaglinide 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 Repaglinide 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: Repaglinide is common in secondary-school and first-year university syllabi. It links to neighbouring topics 1-Piperidinyl compounds, Acetamides, Benzoic acids, so understanding it makes those chapters shorter.
In everyday life: Look for Repaglinide 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 Repaglinide in 20 minutes

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

Frequently asked questions

What is Repaglinide in simple terms?

Why does Repaglinide 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 Repaglinide?

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 Repaglinide.