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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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January 21, 2011

Oh, And While You're At It. . .

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Posted by Derek

Well, this is a question that (I must admit) had not crossed my mind. Courtesy of Slate, though, we can now ask how we can make pharmaceuticals more environmentally friendly. No, not the manufacturing processes: this article's worried about the drugs that are excreted into the water supply.

It's worth keeping an eye on this issue, but I haven't been able, so far, to get very worked up about it. It's true that there have been many studies that show detectable amounts of prescription drugs in the waste water stream. The possible environmental effects mentioned in the article, though, are seen at much higher concentrations. I think that much of the attention given to this issue comes from the power of modern analytical techniques -if you look for things at parts-per-billion level (or below), you'll find them. Of course, you'll also find a huge number of naturally occurring substances that are also physiologically active: can the synthetic estrogen ligands out there really compete against the huge number of phytoestrogens? I have to wonder. To me, the sanest paragraph of the article is this one:

Developing "benign-by-design" drugs poses a series of vexing challenges. In general, the qualities that make drugs effective and stable—bioactivity and resistance to degradation—are the same ones that cause them to persist disturbingly after they've done their job. And presumably even hard-core eco-martyrs (the ones who keep the thermostat at 60 all winter and renounce air travel) would hesitate to sacrifice medical efficacy for the sake of aquatic wildlife. What's more, the molecular structures of pharmaceuticals are, in the words of Carnegie Mellon chemist Terry Collins, "exquisitely specific." Typically, you can't just tack on a feature like greenness to a drug without affecting its entire design, including important medical properties.

And even that one has its problems. That "persist disturbingly" phrase makes it sound like pharmaceuticals are like little polyethylene bags fluttering around the landscape and never wearing down. But it's worth remembering that most drugs taken by humans are metabolized on their way out of the body, and most of these metabolites don't maintain the activity of the parent compound. Other organisms have similar metabolic powers - as living creatures, we've evolved a pretty robust ability to deal with constant low levels of unknown chemicals. (Here's a good chance to point out this article by Bruce Ames and Lois Swirsky Gold on that topic as it relates to cancer; many of the same points apply here).

No one can guarantee, though, that pharmaceutical residue will always be benign. As I say, it's worth keeping an eye on the possibility. But it will indeed be hard to do something about it, for just the reasons quoted above. As it is, getting a drug molecule that hits its target, does something useful when that happens, doesn't hit a lot of other things, works in enough patients to be marketable, has blood levels sufficient for a convenient dose, doesn't cause toxic effects on the side, and can be manufactured reproducibly in bulk and formulated into a stable pill. . .well, that's enough of a challenge right there. We don't actually seem to be able to do that well enough as it stands. Making the molecules completely eco-friendly at the same time. . .

Comments (47) + TrackBacks (0) | Category: Drug Development | Toxicology


COMMENTS

1. NHR_GUY on January 21, 2011 9:23 AM writes...

FIRST!!

If there was ever an argument/proof against Homeopathy, this is it. If Homeopathic curing was real, we could all get well just by drinking tap water since it contains drugs in the ppb region. And even if the drugs weren't there, the water would contain the "memory" of the drug and be efficacious.

Permalink to Comment

2. rodentrancher on January 21, 2011 9:23 AM writes...

There seem to be few known examples of actual, measured environmental impact from administered drugs.

Outside of the agriculture-antibiotic resistance issue, I come up with only two examples: diclofenac and vultures (Indian subcontinent), and pentobarbital and assorted scavengers (multiple locations). Both caused by direct consumption of contaminated carcasses by wildlife, rather than by trace levels in water.

Anyone got anything else?

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3. metaphysician on January 21, 2011 9:37 AM writes...

You know, I really really hate the underlying assumption here: that if something can cause harm at X dosage level, then it by definition causes harm at [vastly smaller than X] dosage level.

You want me to be concerned about three parts per trillion estrogen in the water supply? Show me harmed caused by exposure to 3 parts per trillion.

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4. Anonymous on January 21, 2011 9:41 AM writes...

Just googling pharmaceuticals in wastewater fish and the top hit is about this study:

Aquatic Toxicology, v. 82, no. 1, p. 36-46, doi: doi:10.1016/j.aquatox.2007.01.003

There seem to be plenty more like it.

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5. Anonymous on January 21, 2011 10:01 AM writes...

my favorite topic in this area is the environmental effect of ivermectin on the dung beetle, and the environmental consequences. Much literature. Here's one to get you started...if you have no life.

http://www.jstor.org/pss/2404183

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6. Sev on January 21, 2011 10:06 AM writes...

Caveat: I am not a scientist, nor am I in any way associated with the pharmaceutical industry. However, my wife does study the discipline and I am a regular reader of this blog because it is well written and interesting.

That being said, my concern with pharmaceuticals in waste water is not that they are there. It's how they get there in the first place. It's the culture of waste, particularly in the USA. It's the clear and undeniable fact that the retail pharmaceutical industry, and I'm happy to name names here (walmart, walgreens and etc), treats the end users as nothing more than sales figures. And the end providers (pharmacists) as nothing more than glorified bank tellers, whose sole purpose is to give the customer what they want and shut the heck up.

Rant over, sorry about that. Drugs in the water is not the problem of the chemist. As you so rightly put it there is a fine balance between efficacy and safety in any drug. Again, the problem is not in the chemistry, it's in the end result; Pills being washed down the toilet when grandma kicks the bucket.

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7. CMC guy on January 21, 2011 10:38 AM writes...

Sev: You missed one of Derek's points -- the problem isn't the pills being washed down the toilet after grandma kicks off, it's grandma peeing in the toilet (excreting residual drug and various metabolites) the whole time she's on drug. Asking her to pee somewhere else raises other environmental issues, I think.

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8. Lester Freamon on January 21, 2011 10:40 AM writes...

@6:
If you're on a prescription drug, it will hit its target, dissociate, then get peed out. This is probably the more likely source of drugs in the water than dumping pills down the toilet.

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9. barry on January 21, 2011 11:02 AM writes...

The recent fashion for "hard" (often polyfluorinated) drugs may make hash out of the last decades of data. What we can't metabolize may survive a long time in the environment.

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10. Keith Robison on January 21, 2011 11:10 AM writes...

Have any of the studies tried to distinguish drug disposal from excretion? A few bottles flushed (which is a change-the-behavior issue) could easily swamp out a bit of excretion.

One high-tech solution to the problem is not to redesign the drugs, but redesign the waste processing -- if there really are drugs which get through the system AND are significant hazards, then spiking drug-metabolizing enzymes or microorganisms in during waste processing might be a natural route. Indeed, there may already be lots of bugs out there that do this.

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11. Bob on January 21, 2011 11:20 AM writes...

Low level antibiotics are used as growth promoters in animals and millions of tons enter the environment and you and me by eating.

Whose to say the low level residual antibiotics in food aren't acting as growth promotants in humans and one of the causes of obesity in the US?

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12. barry on January 21, 2011 11:35 AM writes...

re: #10
the immediate threat from the tons of antibiotics in our livestock's feed is that they cultivate resistant organisms in the manure lagoons and in the waste stream just as they do in the animals' guts. The dose needed to act as a growth enhancer is known to a nicety; factory "ranchers" aren't buying/using more than they believe they "need".

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13. yonemoto on January 21, 2011 11:36 AM writes...

"most of these metabolites don't maintain the activity of the parent compound"

IN HUMANS.

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14. John on January 21, 2011 11:42 AM writes...

Welcome to my world. I work for an agrochemical company and we're VERY aware (due to regulatory pressure) where our stuff ends up in the environment. If you guys had to add the sort of testing required for an agrochemical on top of all the other hurdles ... best of luck!

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15. Hasufin on January 21, 2011 11:50 AM writes...

While I can certainly see the potential (mostly unproven or at least unrealized) for environmental harm, I don't think changing the drugs is the answer. As has been repeatedly demonstrated, making effective drugs is already an immensely difficult task.

Shouldn't we instead be looking at wastewater treatment, and preventing those drugs, in addition to other pollutants?

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16. cynical1 on January 21, 2011 12:03 PM writes...

Y'all are so pessimistic! Resistant bacteria = Job security. And we need all we can get of that....

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17. cynical as well on January 21, 2011 12:39 PM writes...

I'm going the throw Occam's razor @10.

Stuffing our pie holes with too much food all day long is the cause of obesity...not some low level antibiotic/growth hormone in the water supply homeopathic treatment.

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18. MTK on January 21, 2011 12:46 PM writes...

@13:

Yeah, John, but try taking out immediate and direct testing on targeted subjects and try testing your compounds on species of different families in models of dubious reliability to decide which ones to develop. Welcome to our world.

Good luck.

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19. Vlad Konings on January 21, 2011 12:51 PM writes...

#17,

And sitting in front of the game box all day. Don't forget lack of exercise.

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20. DCRogers on January 21, 2011 1:14 PM writes...

The widespread problems of wildlife found with screwed-up reproductive systems due to exposure to remnants of excreted birth-control drugs suggests that we're dealing with higher than "homoeopathic" amounts.

Whether it affects design or not, looking at the environmental destination of pharmaceuticals (for example, speed of degradation, or whether they concentrate traveling up the food chain) seems reasonable.

Permalink to Comment

21. CMCguy on January 21, 2011 1:20 PM writes...

As the first quote illustrates drug design can be a delicate balance with compromises necessary to achieve a usable product. Since seems most small molecules hits often have pour water solubility (brick dust) the challenges to med chemists and formulators to interface effectively can be a key element of success. Certain common functional groups or fragments can offer improved water dissolution and many simultaneously increase degradation (immediate and long term, physiologic and environmental) but again may blow activity.

#13 John says it well of the potential difficulty for adding significant fate testing to drugs. Likely many things there would be a negative response at the added costs even if is directly attributable and while some might buy the "green premium" there is already a premium on drugs. There are "Environmental Impact reports" that must be submitted with focus on the dangers/waste from manufacture and not the end drug as much.

Many years ago when pharma calculated how much money was going down the drain there was substantial efforts to improve processes to not lose materials. Another driver later was environmental regs to limit effluents increased, largely started with local/city concerns for drinking supplies, the more so EPA. This is another "outsourcing driver" that can be ignored as US/EU companies have very strict compliance requirements with severe fines even for accidents, and certain countries are rather weak.

Permalink to Comment

22. Eco chemist on January 21, 2011 1:49 PM writes...

I make all my compounds biodegradable. It's stopping them biodegrading that I struggle with.

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23. Plutonium Grandad on January 21, 2011 3:30 PM writes...

This has got to be one of the stupidest things I've read in my 76 years!

#3 Metaphysician hit the nail on the head. If the idiots at Slate did a little homework, they would probably find that there are measurable levels of every kind of bad-news chemical imaginable in our water supply, and yet somehow life goes on.

I'll bet the same pot-heads at Slate complaining about legitimate drugs in the water supply have more illicit drugs flowing in their adolescent veins than we will ever have because grandma pissed out her meds last week.

Love your blog, Derek. You need to write some books. This electronic crap can get erased to easily.

Permalink to Comment

24. anon on January 21, 2011 4:09 PM writes...

I think it is worth remembering that of all the compounds found in the environment only the drugs and its metabolites have been assessed for their safety and toxicity in animals and humans, and passed!

It seems to me that by default these compounds therefor pose less of a problem than the rest of the natural products an waste out there.

Just my 2 cents


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25. GreedyCynicalSelfInterested on January 21, 2011 4:15 PM writes...

More enviro-scare stories from the scientifically illiterate media. There are 97 million cows in the US and I'm sure they are fed larger amounts of antibiotics and whatnot than people get. If they want to get rid of residual organics from wastewater, they can just treat it with ozone and be done with it.

Really, how much does one care if the frogs are growing b@@bs? Show me a picture of tits on a fish and I'll probably suspect that some underemployed biologist Photoshopped it. Predicting disasters and dire consequences for the environment is the stock and trade leftists and environmentalists for at least the last half century. Whether it's global warmists predicting death, drought and starvation unless we give up fossil fuels to Rachel Carlson predicting the birds will all die, it's the same recycled pseudo-religious BS. I've never heard a silent spring yet and never will.

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26. GeoChemGuy on January 21, 2011 4:45 PM writes...

Just an anecdotal observation, but I haven't found many geologists who buy into enviro-scare fads. When you look at things where the "million-year" is the basic unit of time measurement, there is no such thing as "constant." Chemicals come and chemicals go, and life always makes the best of it. Only people who have too much time on their hands worry about shit.

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27. milkshake on January 21, 2011 5:31 PM writes...

I have seen a coke netabolites study done on a river samples that estimated how much of stuff was being consumed in the whole city in Western Europe. (The number was rather high, in kilos per day). I think this is a good methodology that the drug cartels can use to find as yet untapped markets

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28. qetzal on January 21, 2011 5:43 PM writes...

DCRogers (#20) wrote:

The widespread problems of wildlife found with screwed-up reproductive systems due to exposure to remnants of excreted birth-control drugs suggests that we're dealing with higher than "homoeopathic" amounts.

Do you know of data that supports this claim? I.e., not just data on wildlife with screwed-up reproductive systems, but data that implicates birth-control drugs as the cause.

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29. DBS on January 21, 2011 5:48 PM writes...

I'm a grad student in a water treatment research group, and this issue is something we think about quite a bit.
fwiw, one of my colleagues detected ibuprofen and naproxen at 100 ng/L levels in a local river used as a water supply source (see chap 4 of her thesis if you're interested in the details: http://uwspace.uwaterloo.ca/handle/10012/5022). However, we only look at what's in the water and what treatment processes can remove it; we leave the possible health and environmental impacts to others.
Having sat in on a number of presentations on Pharmaceutically Active Compounds in water, my feeling is that the primary ways to deal with this issue are:
1) Better wastewater treatment - membrane filtration (with tight enough molecular weight cut-offs), and some other treatment processes, can remove many pharmaceuticals before they are discharged to the environment
2) Controlled disposal of unused pills - I think some municipalities have started to collect unused pills as household hazardous waste, which is better than letting them get flushed
3) Control of agricultural run-off - it's not just pharmaceuticals that can have hormonal effects in the environment, but also some pesticides and fertilizers.

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30. yonemoto on January 21, 2011 8:46 PM writes...

#28

Unfortunately, it's un-PC to get all anti-birth-control, because, you know, that was the driver of women's lib.

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31. ReneeL on January 21, 2011 9:24 PM writes...

What would help settle some of these concerns is for there to be more actual research on the fate of pharmaceuticals or their metabolites into the environment. Hopefully, the EPA would either do some of this research themselves, or provide grant money to have it done. And hopefully this would happen before the EPA comes under pressure to respond to this environmental 'flavor of the month', based on public alarm rather than solid data.

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32. Algirdas on January 21, 2011 10:17 PM writes...

DBS:

100 ng/L ibuprofen at first seems like a lot, for a synthetic compound "in the wild". But it works out to 86 g per day of input into entire river, assuming 10 cubic meters per second flow rate (2007 Feb data from the thesis you link to, figs 4-5 and 4-6). Given that people take 0.4 g (one time) - 1.2 g (recommended daily max for OTC sale) doses, 86 g is not such a terribly large amount for over 100000 people in the region that puts their waste into sampled river. This is assuming that treatment plant does not remove drug from the input. I can't be bothered to look up what fraction of ibuprofen is metabolized, but it could be that 1 person in 1000 taking the drug will urinate out these 86g which become 100 ng/L in the river if waste water treatment does not remove it. I do wonder, what causes large month-to-month variability in the measured levels, even when river flow is more or less constant? Photodegradation?


As far as hazard presented by these levels of compounds goes, 100 ng/L = 0.1 ppb = 0.48 nM ibuprofen. Assuming a 100 kg person consisting of pure water and say 200 mg ibuprofen in this person, an underestimated therapeutic dose is 0.2g/100kg = 2000 ppb = 9.7 uM. While this comparison is simplistic, I believe we, and fish, are probably safe.

Permalink to Comment

33. qetzal on January 21, 2011 10:28 PM writes...

#30

Huh? Women's lib & being PC have nothing to do with it. If there's evidence that birth control drugs are causing reproductive problems in wildlife, let's see it. If not, let's stop throwing around wild unsubstantiated claims.

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34. Urine trouble on January 21, 2011 11:32 PM writes...

The volume of the ocean is 1.35 billion cubic kilometers. If every person on the planet (6 billion people) took one Tylenol per day for 70 years, and every bit was excreted in their urine, it would amount to about 100 grams per cubic kilometer of ocean.

I think I'll go take a pee now.

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35. Sili on January 22, 2011 9:47 AM writes...

Huh? Women's lib & being PC have nothing to do with it. If there's evidence that birth control drugs are causing reproductive problems in wildlife, let's see it. If not, let's stop throwing around wild unsubstantiated claims.
And even if the evidence is there, the question is one of which is the lesser evil? Imprisoning women or negatively affecting the environment?

Funny how the anti-PC brigade ain't usually much in favour of protecting Nature, but if it can disenfranchise women it's suddenly the best thing since sliced bread.

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36. Chemjobber on January 22, 2011 5:50 PM writes...

A question for those in the know:

There's a lot of fuss about agricultural usage of antibiotics and how it might generate antibiotic resistance. Here's my question: how many of the agricultural antibiotics are also used in humans?

It's been difficult for me to find data on this question. Monensin seems to be one of the key agricultural antibiotics; this one doesn't have any human exposure. Seems to me -- what's the harm? At the same time, it is my understanding that fluoroquinolones are used for both humans and animals. Not knowing anything about anything, this just seems like a bad idea (potentially.)

Anybody have any thoughts/expertise?

Permalink to Comment

37. barry on January 22, 2011 8:37 PM writes...

re #36:
if bacterial resistance were compound- (or even class-)specific, the worry would be less. Alas, a lot of the resistance is in the form of export pumps that can keep a broad variety of small molecules out of the bacteria (beta lactams are different, in that they act in the periplasm, rather than in the cytoplasm). Since very different bacteria have been found to swap resistance/pump genes on plasmids, cultivating resistance to one class of "growth enhancers" can have real health effects on humans taking antibiotics that may be structurally unrelated.

Permalink to Comment

38. Telescope - wrong end of on January 23, 2011 2:17 PM writes...

"Benign by Design"... just another burden on the shoulders of the over-asked Med Chemist?

Think again - it highlights the central challenge for our industry: why do we persist in making the kind of molecules that are actually expected to be toxic, unless proven otherwise (and then usually only through massive cost and dosing sleight-of-hand)?

"Benign by Design" should start with the patient: he's ill enough.

Permalink to Comment

39. The Blue Maharaja on January 23, 2011 2:36 PM writes...

#38 Interesting point, Telescope.

However blase Pharma CEO's might be about eco-systems, you can be sure they're cr***ing themselves about pipeline attrition due to non-mechanism-related tox.

Perhaps we should start with basic toxicology training for undergraduate chemists - anyone know one with any?

Permalink to Comment

40. Behbeh on January 23, 2011 5:02 PM writes...

The estrogenic effect of trace contaminants in water is well documented. The effect is observed in fish and amphibians and caused by a number of different compounds, some herbicides/pesticides but also estrogen derivatives used in contraception which are more potent than estrogen itself.
For a well cited review (focusing on fish) se
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1518861/

Permalink to Comment

41. Chemjobber on January 23, 2011 6:58 PM writes...

@barry -- thanks for the comment; I think I understand better now.

Permalink to Comment

42. Anthony Bishop on January 24, 2011 2:04 AM writes...

If only we were so good at designing drugs that it was possible to add 'environmentally friendly' to the very long list of desirable properties..................

Permalink to Comment

43. simpl on January 24, 2011 9:27 AM writes...

This is a real area of concern, all right.I remember being shocked at first exposure when an HSE workshop reviewed some of the literature. A few weeks after, I read newspaper reports of diclofenac causing the extinction of three species of vulture in India, and am still struggling to guess a mechanism that could lead to sufficiently high levels of diclofenac in cow carcasses.
So I'm not really happy with some correspondants' attempts to argue away the topic, if only because the FDA already requests its coverage in environmental impact statements. Your chemical development people already commission toxicity studies in algae, fish and mammals - have a look at some of this data, you might get ideas of molecules where an environmentally clean successor would bring some value. There is even software to predict the environmental impact of intermediates and by-products. Ours was cobbled together between research and environmental chemists with the help of a local university.

Permalink to Comment

44. Virgil on January 24, 2011 10:29 AM writes...

#6 Sev - You have hit the nail precisely on the head.

We cleaned out out bathroom cabinet a few weeks ago, and came up with 20+ bottles of various pharmaceuticals that were past their use-by-date.

I trundled off to the local CVS with a bag full of bottles, and kindly asked the pharmacist to dispose of them. Their response was "we have no such facility for disposal here... just flush them down the toilet". The response was the same at Rite-Aid.

This leads me to conclude that the waste-water coming out of your local Rite-Aid/CVS/Wal-Greens likely contains ridiculous amounts of disposed pharmaceuticals.

Permalink to Comment

45. Conservative who isn't Misogynist on January 24, 2011 2:13 PM writes...

#35 Sili

I've always thought that civilization was built basically to impress women. All the technology, inventions (including drugs) that we surround ourselves with was pretty much invented to impress girlfriends, wives, or prospective versions thereof.

If it was just us men on the planet, we'd still be living in caves. We WOULD have nuclear weapons, and maybe plasma TVs.

Permalink to Comment

46. Anonymous on January 24, 2011 9:27 PM writes...

#40: The well-cited review that you posted contains the following line as part of its conclusion:

"To date, there is no evidence to suggest
that fish, or any other aquatic organisms,
are affected adversely by living in and
bioaccumulating estrogenic chemicals."

While I think the matter is worth considering and studying, this review suggests that so far, studies have not found any direct risk.

Permalink to Comment

47. qetzal on January 24, 2011 10:31 PM writes...

Following up on Anonymous #46, the review also points out that there are various chemicals used in petrochemicals, plastics, soaps, and detergents that are estrogenic, and that some of these are used in hundred thousand ton annual amounts. It further notes that women on birth control drugs typicall excrete estrogens in conjugated and biologically inactive forms.

So the review cited in #40 supports the claim that man-made estrogenic chemicals are disrupting reproductive systems in wild life, but it does NOT support the original claim in #20 that pharmaceuticals are doing so.

Which is not to downplay the significance of the effects that may be caused by these estrogenic chemicals. But the topic of this thread is whether pharmaceuticals have deleterious environmental effects, not whether other industrial chemicals do.

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