Dutasteride is of the same class of drug as Propecia and Proscar - the so-called 5-alpha-reductase inhbitors. These inhibit the enzyme of this name from converting testosterone into dihydrotestosterone.
Interestingly, the class is useful for both prostate hyperplasia (proscar) and hair loss (propecia) - these two are the same molecule. Avodart, which has been approved for prostate hyperplasia, was in trials for hair loss awhile back, but these were since dropped.
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This post appeared originally on 8 Feb 2006 at the old site for this blog. A frequent reader and commenter, Joe, suggested that I repost it here as it illustrates many common problems with clinical trials of botanical medicines.
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tags: Ask a Science Blogger, male birth control pill, contraceptive
The human egg at the moment of fertilization.
Image: National Museum of Health and Medicine.
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This may be a silly question, but in a molecule such as this, where there's a "floppy" looking bond (at the upper N), does the molecule fold up into different configurations like a protein would? Would that affect how the drug works in the body, or is there generally enough energy available to unkink it?
Hey Xerxes: The N you're talking about is involved in two interesting bonds; one is that it is next to a carbonyl, making it an amide. Amides (like in proteins) have some double bond character which makes the system planar. This is one way a protein maintains its structure. But here, the N is also bound to an aromatic ring (a very bulk one at that with the 2 CF3 groups). The lone pair electrons on the N will want to stay perpendicular to the plane of the benzene ring, too. I don't know which force will win (whether the electrons will choose to stay in line with the aromatic system or go towards the C=O bond) but it is likely somewhat rigid. Another factor is that the CF3 groups will not want to bump into anything, so the benzene ring will have to be oriented to avoid "steric clash."
This is a small molecule, and probably has limited mobility, and lacks the secondary structure that you refer to in proteins. Likely, this molecule binds to its target in one conformation.
I'd be interested to know the role of the aromatic ring on this drug, too, but I imagine that might require a crystal structure of it bound.
Xerxes
Looks like that upper bond is an amide conjugated to a phenyl ring, so I'm guessing that it probably doesn't have much conformational freedom. However, as I understand it, most drugs are designed to not have too much floppiness so that the entropic loss of them binding their target doesn't completely kill their binding constant.