Nexium: The Dark Side Of Pharma

January 20, 2017

The giant drug maker AstraZeneca announced last month that they would be firing 700 people across the country. in 2017. I know some of them. This one’s for you, guys.

I am usually supportive of the pharmaceutical industry (1). People who routinely criticize it usually have no idea how difficult and expensive it is to get something from the lab to the pharmacy. Also, many people think that drug companies don’t provide innovation, and do little more than manufacture something that the NIH or a university came up with. This could not be more wrong. Pharmaceutical companies have discovered and developed drugs that have had an enormous impact on human health. They do all the heavy lifting.

But, there are exceptions. For example, AstraZeneca marketed a drug that should have never been approved in the first place: Nexium. They did it solely for money—without any benefit to society— and it sure worked out well for them. It made AstraZeneca almost $48 billion during the past decade, without any innovation or benefit to people who had previously been taking Prilosec to control their heartburn. They didn’t deserve a penny of it. The “purple pill” marketing plan was brilliant.

Following is the story of how the company was able to get away with this.

First, whenever you see a drug name starting with “Es,” it is time to be suspicious:

Omeprazole (Prilosec)

Esomeprazole (Nexium)

Aside from the “Es,” the names are identical, which makes perfect sense, since the two drugs are essentially the same. But there is one tiny (and usually insignificant) difference that enabled AstraZeneca to replace  its Prilosec patent, which ran out in 2001, with Nexium (2).The chemistry here is rather difficult to explain, but I’ll try anyhow. It’s called optical isomerism.

Any molecule that contains a carbon atom (3) that has four different substituents (atoms, groups, rings…) bound to it is, by definition, asymmetrical. In the figure above, the carbon atom (gray) is attached to four different substituents, the spheres shown in red, blue, yellow, and green. Although chemically identical—the two molecules will have the exact same properties (melting point, boiling point, solubility in water…)—they are not identical in every way. Asymmetric molecules exist in two forms (4) called enantiomers – mirror images of each other. They have the same substituents on carbon, but it is impossible to superimpose one enantiomer on another—the acid test for identity.

This explains the “Es” prefix.

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