Smarts Call!

[kyburg]

Do I have anyone on my friends list who can tell me the difference in structure - based on the naming nomenclature - of these two substances:

hexachlorophene
chlorhexidine

One used to be used surgically when I was a tot - and was removed from the market. The second is an up and coming substance being brought to market to kill bird flu as a topical hand wash....

Looking it up, it's already in use as a mouthwash and so forth - mosting for HIV applications.

Anyone?

Comments

[7leaguebootdisk.livejournal.com]

I never took ochem. I would not have guesed their structure (yes, I googled it, should have just gone to wikipedia).

the suffix -phene...

[tomlemos.livejournal.com]

indicates that there is benzine as part of the substance.

Re: the suffix -phene...

[tomlemos.livejournal.com]

at least that's about all I was able to gather on a quick search. :)

[wednesday]

Chlorhexidine is in common usage over here -- the mouthwashes are OTC (although still offered by prescription in larger bottles, and used by hospitals) for gingivitis, post-oral-surgery stuff, &c. &c. You can also get wound wash sprays for first aid kits made with the stuff.

[foogod.livejournal.com]

I'm not good enough with chemical nomenclature to be able to derive structures off the top of my head, but based on some basic research from web sources, It looks like these compounds sound somewhat similar but are actually completely different structurally.

Hexachlorophene at ChemFinder
Chlorhexidine at ChemFinder

From what I can tell, Hexachlorophene was removed from the market in the US originally due to suspicions that it might cause cancer, but since that time as far as I can tell nobody has found any evidence to suggest that this is actually the case, and frankly it looks pretty safe. It sounds like it's still used fairly heavily in over-the-counter things (soaps, etc) in many parts of the world too..

As noted, chlorhexidine gluconate is dispensed quite readily as an antiseptic mouthwash by dentists in the US for such things as gum disease (gingivitis). I haven't found a whole lot of toxicity information for it, but what I have found suggests that it can cause hearing issues in extremely large dosages, but such dosages are pretty unlikely to happen in general practice.

[mrotakki.livejournal.com]

Without the standard IUPAC nomenclature, it's difficult to really appreciate the difference in structure since a lot of names for substances produced industrially are often times the trademark name, or a specific identifier created by the company that produced it.

I'm mostly curious why the sudden interest in the two compounds since, as far as I know, they are totally unrelated to each other and are the last thing anyone would normally just randomly think about.

[kyburg.livejournal.com]

This is someone violently allergic to ampicillin who can take penicillin without any issue - and has a father who was anaphalatically allergic to penicillin. The difference? Ampicillin has a sulfur group in the bottom right corner of its structure - I got to look it up that summer I was a pharmacy messenger. (BTW, don't piss off pharmacists - they loved "Quincy" as a television show, and could kill you a gadzillion different ways without anyone knowing. Mythbusters could add one of them to their team and I'd cheer.)

Also, chalk it up to having an excellent memory - and when the chatter came down about chlorhexidine came up this morning, it triggered the memories I had of Mom working in the hospital and the flack over Phiso-Hex that came down back in the early seventies (Hexachlorophene).

[mrotakki.livejournal.com]

Hokay.

Just curious.

I spend a lot of time thinking about organic materials, and this is still something that I would never have thought about. Well, the two specific compounds. I think about organic chemistry all the time.

[kyburg.livejournal.com]

I had organic chemistry in college in 1979. I recall that there is a method to the nomenclature (this structure is so, and the second syllable means blah), but I can't recall it.

Bad? I think I still have the textbook someplace.

[mrotakki.livejournal.com]

You're referring to the IUPAC nomenclature rules.

The names you provided aren't specifically IUPAC as far as I know.

IUPAC has also undergone fairly significant changes over the past couple of decades in terms of how things are prioritized and named. What you have in your old textbooks could be outdated.

[eve-dallas.livejournal.com]

Having been banned from my college chem lab after my first trimester, I have no clue where to look for either of those things. I do remember my mom always having a big bottle of PhisoHex around when I was growing up.

[kyburg.livejournal.com]

Banned? Oh, this I gotta hear.

[eve-dallas.livejournal.com]

First, you need to know that I went to college in the same town in which I went to high school. In high school chem., an experiment of mine got so out of hand that the whole science wing was flooded with chlorine gas and had to be evacuated. Three weeks later, I approached the experiment in a different way and scattered a whole lot of mercury around the lab. In my defense, the second mishap was as much the fault of my chem instructor as it was mine.

When I started college, my major was microbiology. I didn't really want it, but my dad was pushing for me to study a science, so I chose that. In my first trimester in chem. lab, the first thing I did was swallow a bunch of acetone and was sent immediately to the university medical center for treatment. Next I followed the instructions for an experiment exactly and, while everyone else's resulted in a white powder, mine resulted in green goo. The last straw was when I turned the wrong way holding a large test tube full of a liquid I'd just heated and burned my lab partner. As it turned out, my Chem professor knew my high school Chem teacher.

For the next trimester, I changed my major to Russian with minors in Spanish and Political Science. It's really hard to finish a degree in Microbiology when you are not allowed into a chemistry lab.

[kiyone.livejournal.com]

My friend tells me she's infamous at Smith for making Flintstones Vitamins explode in her lab. She, too, was not allowed to do any sort of experimentation after that matter.

[eve-dallas.livejournal.com]

And nor was I, in high school or in college. Oddly enough, I did very well in biology.

A year after I had chemistry in high school, my next sister had chemistry and had several not-quite-as-dramatic upsets in lab. My next sister after that ended up with the same teacher and, when she could only get her bunsen burner to light ABOVE the flint, he went down to the office and had her schedule redone so she had the other chemistry teacher thereafter. Five years later, my brother David started there, then another brother, then three more sisters. My chem. teacher refused to teach any of them!

[ersatzinsomnia.livejournal.com]

MSDSes tend to hyperventilate, but they're the best source if you're looking for toxicology information on substances. Here:

hexachlorophene
chlorhexidine

This info is pretty widely available if you just google for "MSDS" with the substance. There are dozens of MSDS indexes out there and none seem to be complete or I'd just point you at a general one. They also contain the IUPAC name for each, so you can construct it on paper if you really care...

[kyburg.livejournal.com]

Just what I needed. Exactly. Thanks!