chemistry

Oxaliplatin

Oxaliplatin 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 Oxaliplatin rather than just read about it. In short: Oxaliplatin, sold under the brand name Eloxatin among others, is a cancer medication (platinum-based antineoplastic class) used to treat colorectal cancer. It is given by infusion into a vein.

Key takeaways

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

Reference excerpt

Oxaliplatin, sold under the brand name Eloxatin among others, is a cancer medication (platinum-based antineoplastic class) used to treat colorectal cancer. It is given by infusion into a vein. Common side effects include numbness, feeling tired, nausea, diarrhea, and low blood cell counts. Other serious side effects include allergic reactions. Use in pregnancy is known to harm the baby. Oxaliplatin is in the platinum-based antineoplastic family of medications. It is believed to work by blocking the duplication of DNA. Oxaliplatin was patented in 1976 in Japan and approved for medical use in 1996 in Europe. It is on the 2023 World Health Organization's List of Essential Medicines.

Medical uses Oxaliplatin is used for treatment of colorectal cancer, typically along with folinic acid (leucovorin) and fluorouracil in a combination known as FOLFOX or along with capecitabine in a combination known as CAPOX or XELOX. It also has uses in pancreatic cancer and stomach cancer or esophageal cancer. It may also be effective against breast cancer, germ cell tumor, ovarian cancer and non-small-cell lung cancer.

Advanced colorectal cancer Oxaliplatin by itself has modest activity against advanced colorectal cancer. When compared with just 5-fluorouracil and folinic acid administered according to the de Gramont regimen, a FOLFOX4 regime produced no significant increase in overall survival, but did produce an improvement in progression-free survival, the primary end-point of the phase III randomized trial.

Adverse effects Side-effects of oxaliplatin treatment can potentially include:

Neurotoxicity leading to chemotherapy-induced peripheral neuropathy, a progressive, enduring and often irreversible tingling numbness, intense pain and hypersensitivity to cold, beginning in the hands and feet and sometimes involving the arms and legs, often with deficits in proprioception. This chronic neuropathy may also be preceded by a transient acute neuropathy occurring at the time of infusion and associated with excitation of voltage-gated Na+ channels. Fatigue Nausea, vomiting, or diarrhea Neutropenia (low number of a type of white blood cells) Ototoxicity (hearing loss) Extravasation if oxaliplatin leaks from the infusion vein it may cause severe damage to the connective tissues. Hypokalemia (low blood potassium), which is more common in women than men Persistent hiccups Rhabdomyolysis In addition, some patients may experience an allergic reaction to platinum-containing drugs. This is more common in women. Oxaliplatin has less ototoxicity and nephrotoxicity than cisplatin and carboplatin.

Structure and mechanism The compound features a square planar platinum(II) center. In contrast to other drugs of the platinum-based antineoplastic class of drugs cisplatin and carboplatin, oxaliplatin features the bidentate ligand trans-1,2-diaminocyclohexane in place of the two monodentate ammine ligands. It also features a bidentate oxalate group. The three-dimensional structure of the molecule has been elucidated by X-ray crystallography, although the presence of pseudosymmetry in the crystal structure has caused confusion in its interpretation. According to in vivo studies, oxaliplatin fights carcinoma of the colon through non-targeted cytotoxic effects. Like other platinum compounds, its cytotoxicity is thought to result from inhibition of DNA synthesis in cells. In particular, oxaliplatin forms both inter- and intra-strand cross links in DNA, which prevent DNA replication and transcription, causing cell death.

History Oxaliplatin was first synthesized in 1978 at Nagoya City University by Yoshinori Kidani. It was later developed in Europe as a less toxic and more effective alternative to cisplatin. It gained European approval in 1996, and approval by the U.S. Food and Drug Administration in 2002. Generic oxaliplatin was first approved in the United States in August 2009. Patent disputes caused generic production to stop in 2010, but it restarted in 2012.

Patent information Eloxatin was covered by patent numbers 5338874 (expired 7 April 2013), 5420319 (expired 8 August 2016), 5716988 (expired 7 August 2015) and 5290961 (expired 12 January 2013) (see Electronic Orange Book patent info for Eloxatin). Exclusivity code I-441, which expired on 4 November 2007, is for use combination with infusional 5-FU/LV for adjuvant treatment stage III colon cancer patients who have undergone complete resection primary tumor-based on improvement in disease free survival with no demonstrated benefit overall survival after 4 years. Exclusivity code NCE, New Chemical Entity, expired on 9 August 2007.

References

Illustrations

Worked examples

Example 1 — a first encounter with Oxaliplatin

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

In research: Oxaliplatin 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 Oxaliplatin 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: Oxaliplatin is common in secondary-school and first-year university syllabi. It links to neighbouring topics Ammine complexes, Oxalato complexes, Platinum(II) compounds, so understanding it makes those chapters shorter.
In everyday life: Look for Oxaliplatin 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 Oxaliplatin in 20 minutes

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

Frequently asked questions

What is Oxaliplatin in simple terms?

Oxaliplatin, sold under the brand name Eloxatin among others, is a cancer medication (platinum-based antineoplastic class) used to treat colorectal cancer. It is given by infusion into a vein.

Why does Oxaliplatin 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 Oxaliplatin?

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 Oxaliplatin.