Articles by: See Arr Oh

Roll-On Hormones, now on ESPN

Here’s something you don’t see every day: new drugs advertised on ESPN. Especially one you apply to your armpits.

Actual Axiron logo: Crash-test dummy with rainbow B.O.?
Source: Eli Lilly

Enter Axiron, Lilly’s new therapy for hypogonadism (decreased hormone production from the testes), a whopping dose of male sex hormone testosterone – 60 mg, compared to the normal 5-10 mg produced in the body – delivered in a convenient deodorant applicator. Lilly’s product capitalizes on its unique delivery system, but it’s actually a “me-too”: AndroGel (Unimed, Abbott) has been on the market since 2000.

Now, I don’t usually glean my drug info from sports networks, but I understand the angle – recall that Bears coaching legend Mike Ditka used to shill for Levitra. I also adore the way modern-day marketing really lasers the lingo at the target audience. Look at that brand name: AXIRON (short for ‘axillary application?’) Split down the middle, the words “Ax” and “Iron” appear, both of which imply manliness, hard work, and toughness. Allow me to suggest a few more, for when the next underarm drug rolls out:

Hammersmash | T-Power | Fueltron | Steamroller | Blasterol

Although hypogonadism appears in the official prescribing information, there’s a huge market for off-label use. Sex hormones are big business; a brief YouTube search suggests that Axiron finds applications for decreased sex drive and female-to-male transgender therapy. My favorite find? Muscle Ch3mistry (NSFW!), an online message board where bodybuilders inquire whether anyone has used Axiron as “male enhancement,” for working out, no doubt.
Readily available, skin soluble testosterone also raises some complex social issues. Lilly’s own prescribing information notes that the product can induce early onset puberty if children touch clothing saturated with delivery gel (See Section 17.2 for the gory details). And who actually sees these ads?’s own Media Kit indicates the primary users of its content are “young, affluent, male avid sports fan[s],” with a median age of 29 – perhaps the population most likely to abuse this drug for potential performance gains, exercise or otherwise.
By December 9, 2012 2 comments chemical safety, fun

LeBron James Promotes Sheet-y Science

It’s been quite a year for the NBA All-Star: claiming his first NBA Championship, winning gold in the 2012 London Olympics, and now…promoting dietary supplements?

The product in question, Sheets®, offers variations on the “breath strips” made popular roughly a decade ago. Each strip contains different GRAS additives, such as melatonin to aid sleep, or caffeine in the Energy Sheets®. Despite the fecundity of the exclamation points in the FAQs, or even the curious swath of ‘beautiful people’ who promote this product, I’d be willing to give it a pass, if it weren’t for one teeny, tiny detail: the “Science page.”

Here’s the full scientific statement:

“It’s simple…Sheets® solve problems! Sheets® are paper-thin, individually wrapped pocket-sized strips. No cans. No bottles. Simply place on tongue and your problem dissolves. How? Sheets® are packed with nutrients/vitamins and other active ingredients that, when placed on tongue, will begin to dissolve allowing for easy digestion.

Hang on a second….AAAAAUGH!

OK, all better now. Let’s see if we can break that down further for our discerning audience. Apparently, the science of Sheets® involves dissolution (“place on tongue”) followed by digestion of nutrients/vitamins. Did everyone get/understand that, or should I repeat/rehash it again? Never mind those goofy pictures with the colorful stamped film, which looks uncomfortably like another orally administered molecule



Let’s go to our good friend Google patents to find some real science on this sheet-y product. I dug up two documents in short order: US patent 4,713,243 (Johnson & Johnson, 1987) and US 6,419,903 B1 (Colgate, 2002). Both patents describe various technologies for impregnating thin, extruded films of soluble polymer with medicaments for oral administration. Translation – edible drug strips.

The base polymer of choice, even 25 years ago, seemed to be hydroxyalkyl cellulose, one form of which we call pullulan. Various swell-able filler polymers, such as gelatin, corn starch, or PEG (polyethylene glycol) mix with the pullulan to regulate its toughness and stiffness, as well as to serve as a carrier for the active ingredients. For the Colgate breath strips, these include zinc compounds or alpha-ionone, which help to fight volatile sulfur compounds (VSCs) in your mouth. The J&J patent reaches even further, engineering strips to fight bacteria (sulfadiazine), pain (potassium nitrate), or to reduce swelling (hydrocortisone).

Honestly? I was most surprised by the level of formulation science that goes into each strip: viscosity tests, dispersion, dissolution, adherence, blending, and extrusion. Sounds like the perfect job for a p-chemist.

Just don’t get LeBron involved. Please.

Lab Muppet Theory

Quick: What do Pinky and The Brain, Kirk and Spock, Bunsen and Beaker…and your research group all have in common?

Give up? They all subscribe to “Muppet Theory,” a very recent label on a very old phenomenon. As Slate writer Dahlia Lithwick explains, Muppet Theory reprises the age-old struggle between archetypes: Order fighting Chaos, Kermit against Animal, maybe even mustard vs. ketchup.

"Are you thinking what I'm thinking, Pinky?" "I think so, Brain, but isn't Nietzsche a type of cheese?"

Nietzsche formalized this philosophy in 1872 (thanks, NPR!) with his Apollonian (order-seeking) and Dionysian (chaos-loving) personae, stating that true high art comes from the successful fusion of both aspects in one venture.  Well, scientists have argued these points for the last three centuries! Consider the following quotes from two chemistry legends:

“A tidy laboratory means a lazy chemist.” Jöns Jacob Berzelius (1779-1848)

“Fortune favors the prepared mind” – Louis Pasteur (1822-1895)

Right there, you have “Muppet Theory” in action. Lab Order Muppets (Brain, Spock, Bunsen) contribute careful data collection and deep analytical thinking, while the Lab Chaos Muppets (Pinky, Kirk, Beaker) stir the pot, following gut instincts and making wild assumptions. In my experience, Lab Order Muppets are department-builders, sturdy rocks in the storm that can manage conflicts. Lab Chaos Muppets have the devil’s luck, write roguish autobiographies, and often enjoy pop-culture “crossover” success.

So, which Lab Muppet type are you? I’ll disclose my “Muppet type” in the comments, but only after I hear from a few readers.

P.S. While researching this post, I came across this fantastic Agilent ad.

Nitroolefins – The Crying Game

(This post was written for the ‘Toxic Chemicals’ carnival, over at ScienceGeist)

Let me tell you about the time I broke down crying in lab. No, it wasn’t an epic breakup, or even a death in the family. It was…a nitroolefin.

Many summers ago, I worked as a pharma intern, a small flywheel in a then-huge drugmaking machine. My supervisor, a kind, safety-conscious scientist, begged me to come straight to him if I had any questions about my reactions.

We were synthesizing a small nitroolefin – 2-nitropropene, to be exact – for some nitro-Michael additions. If you look at the Org. Syn. prep, it warns, right at the top in red letters, that the compound is a potent lachrymator. The term, from the Latin word for “teardrop,” describes compounds that irritate the eyes to such an extent that tears freely flow.

I carefully piloted the reaction, distilled the greenish-yellow product, and then watched it run up my TLC plate. Beautiful! Now, I just needed an NMR sample.

Gingerly, I dissolved a drop into some chloroform. Forgetting for an instant, I pulled the NMR tube out of the hood to cap it, and within seconds crumpled to the bench. It felt as if someone had stabbed smoldering iron toothpicks into my eyes. I stumbled around until my labmates dragged me over to the eyewash; later, I became well acquainted with our local safety officer. My eyes remained bloodshot for the rest of the day. Lesson learned: Lachrymators are not to be taken lightly! (I’ve experienced similar, though milder, reactions to benzyl bromide and thionyl chloride).

For those younger chemists thinking about summer lab work, take a few minutes to find out if your reagents might cause uncontrollable crying. Cautious handling, and a well-fit respirator, can go a long way towards your future safety and comfort.