OK - a little professional rant here about the evils of the drug companies. Stick with me - this is longish and delves into chemistry and molecular structures, but I promise it will make sense and be worth it in the end.
When drugs lose their patent and generics are about to hit the market, the Evil Drug Companies have several nasty little tricks to extend the patent. Once way is getting approval for new indications, another is bringing lawsuits against the generic manufacturers for technicalities, and another is by coming out with a "new" copy-cat drug that they market as being better than the original. It is this third case I would like to discuss today.
Because of the way that carbons work in molecular structures, sometimes there are "chiral carbons" - carbons where the other molecules that stick to them can be arranged in one of two specific ways. This makes it so that there are essentially two drugs with the same chemical structure, but that are put together just slightly differently. The molecules are non-superimposable mirror images of one another. A great visual analogy to this is your hands - they both have a thumb and four fingers, but you have a right and a left and no matter how you turn them, they will never be the same. In fact, sometimes these carbons are referred to as "right-handed" or "left-handed" because of some optical effects they have in solution.
Anyway, usually, they way the molecules (fingers) are stuck onto the carbon (hand) are random and often it turns out to be about a 50/50 mix when the drug is made in the lab (it is possible for there to be other ratios but how and why that happens is complicated and beyond the scope of this post). Sometimes, both forms of the drug work just fine, sometimes there is one or the other that is responsible for the activity and/or side effects of the original mixture. Think of the activity sites in the body as gloves - sometimes you have a stretchy knit mitten - anything vaguely hand-shaped will do - but sometimes you have a tailored leather right handed driving glove and only the right hand of the person the glove was designed for will fit it. It is the same way with drugs- sometimes that chiral carbon matters, sometimes it doesn't.
So... the Evil Drug Companies, seeing that their big earner is about to lose its patent, will sometimes try to figure out which of the molecules is the active or more active form. They can usually then either figure out how to manufacture just that type or how to separate the two molecules after they are made. This does two things - it usually makes the process more expensive and it means that they can patent this "new" drug as a brand name drug. With sufficient advertising, they can even make people believe that this "new" drug is better than the old one. That is usually a lie. Sometimes both of the molecules were active and one was just chosen for its patentability. Sometimes the inactive or less active one was just "junk" - essentially taking up space but not doing anything. Rarely is the side effect or efficacy rate significantly changed by these little tricks.
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Some examples:
Claritin (loratadine) 10 mg and Clarinex (desloratadine) 5 mgSee? They are using the right-handed molecule (ergo the "des" prefix on the generic name) and only using half as much, because they have taken out the left-handed loratadine that presumably was inactive. Now they have a drug that can be prescription only and brand name! Yay! Money for the Evil Drug Company!
Celexa (citalopram) vs Lexapro (escitalopram)This one is a little harder to do the direct comparison because it comes in multiple dosage strengths. (In this care, it is an antidepressant that can work at different strengths for different people.) However, in general, the Lexapro doses are half the Celexa doses. This time it is the left-handed molecule that is used (es = S = sinister = left).
Prilosec (omeprazole) 20 mg and Nexium (esomeprazole) 20 mgOooh! My
favorite. Remember all those ads about the "Purple Pill"? Remember when they started talking about the "NEW Purple Pill" and the pill got these adorable gold stripes on it? They were trying to get people to stick with the brand name product when omeprazole went generic and the generics were shockingly no longer in a purple capsule.
Horrors! It won't
work if it is not in a purple capsule! They touted all this "evidence" that Nexium (oooh! even the name implies progress!) worked better than omeprazole, but if you look at this mathematically - if the left-handed molecule is the one that works and the dose of both the mixed drug omeprazole (active and inactive) and the "pure" drug esomeprazole (all active) is 20 mg, which would you expect to work better? Perhaps the one with twice as much active ingredient?
Shocking. But they don't want you to take two of the cheap-o $0.60 pills when you could take their $6.00 per pill Purple Pills! Look! they are shiny! and Purple!
Thalidomide Thalidomide is a chiral drug too and only one of its molecules is responsible for the terrible birth defects seen in children of women who took it during pregnancy. However, it (and many others) cannot be marketed as a single type of drug because the human body can interconvert the two types of molecule and change the beneficial form into the teratogenic form after the drug is consumed. Some other drugs have this conversion happen too, but it can be of little or no consequence if the other form is benign or beneficial.
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So, the take home message - when your doctor prescribes something - especially something you have seen a lot of commercials about - it is worth asking the doctor and/or your pharmacist if there is something older, cheaper, and just as good. Often, there is. Keep your money, don't give it to the Evil Drug Companies!
For those of you dorks interested in details:
Chirality the basic background chemistry
Enantiomers includes a list of drugs where this technique has been used