Archive for May 7th, 2007

WARNING: This is an R-rated blog post and deals with issues related to sexual dysfunction. Do not read further if you are easily offended. If you choose to read from this point forward please do not raise objections later. You have been warned.

We’ve only had it up for six weeks but already it’s clear that sex is of interest on the ChemSpider website. Excuse me you say???

Yes indeed…as with the rest of the web the subject of the birds and the bees proliferates even onto the ChemSpider website. We expected to have people submitting crude comments to the blog, sending inappropriate emails to the chemspider.com domain and even attempting to flirt on the ChemSpider skype number. All happened. (Layla from Belgium..if you are reading I am happily married and you have been blocked). The interest in erectile dysfunction drugs at ChemSpider itself seems to actually be scientific in nature (well maybe).

One of the most common searches in the domain on erectile dysfunction (ED) chemicals is, in many ways to be expected, for Viagra. The searches have generally been by trade name but also structure-based searches of sildenafil. Viagra is not the only chemical of interest. Both Cialis and Levitra are also showing a number of hits. We’ve also seen inquiries for Yohimbine and Ginseng and we’re now waiting for a search on powdered rhino horn. Okay, so how many of these searches are by lay people and how many by chemists? If these searches are by non-chemists what are they trying to find out about these chemicals at ChemSpider? Are they looking for side effects, consumer reports, suppliers or prices? We certainly don’t advertise for the big drug companies so they are not being drawn to our site in this manner.

It’s unlikely that they have interest in the physicochemical properties. Maybe they are instead interested in the trade names, synonyms and systematic identifiers. It appears this may be so since a recent submission to the data curation section of ChemSpider commented that we were actually lacking certain synonyms for Viagra.

Synonyms

Maybe these searches were actually performed by chemists comparing what types of SMILES each of the erectile dysfunction drugs would deliver or even how big an InChI each had. Below are listed three of the most common ED drugs with their relative SMILES and InChIs. It is clear that Viagra gives bigger SMILES than either Levitra or Cialis and that Viagra also delivers more InChI than its competitors. This is a common situation for these systematic identifiers…the bigger the InChI the bigger the SMILES. There is no situation we are aware of where a small InChI doesn’t give rise to at least a little SMILES.

SMILES and InChIs

We have also noticed some combined searches occurring on ChemSpider :“ generally combinations of common drugs with erectile dysfunction drugs. For example, a) Viagra with Aspirin, b) Levitra with Glucosamine and c) Cialis with Atorvastatin. The purpose of such combinations is clear: For a) performance without a headache, b) the possibility of sexual enhancement while simultaneously preventing stiffness in the joints (isn’t that an oxymoron) and c) improved sexual performance combined with anti-stroke (personally I believe pro-stroke makes more sense in this case).

It was recently brought to our attention that Bremelanotide, a derivative of Melanotan, is about to go into a phase III clinical trial. Originally, the peptide Melanotan II that bremelanotide was developed from was tested as a sunless tanning agent. In initial testing, Melanotan II did induce tanning but additionally caused sexual arousal and spontaneous erections as unexpected side effects in eight out of the ten original male volunteer test subjects. Clearly this caused concern on the beaches and likely gave rise to a few SMILES as a result (excuse the pun). As shown below this complex structure is far more complex in nature than the other commercial ED treatments and may have the side benefit of providing a tan!

Bremelanotide

Breme SMILES

A Large InChI from Bremelanotide Clearly Also Gives Large SMILES

With the ongoing surge of interest in the erectile dysfunction chemistry exposed at ChemSpider the team is presently considering the formation of a subset database for submission to PubChem. This will likely get submitted as the NAKED Chemicals database since the database will contain the Nomenclature, Acronyms and Knowledge of Erectile Dysfunction drugs, metabolites and related materials. Considering the usage of these materials the NAKED Chemicals database will likely arouse a lot of interest.

ChemSpider has been set up with the intention of providing value to the chemical community in various ways. Direct usage of the ChemSpider system and its associated services is the most direct manner but we have made a commitment to ourselves to ensure that we return value to the date source providers supporting ChemSpider. We intend to do this through the process of curation as well as by providing data to the public domain.

In this regard ChemSpider has submitted our first database to PubChem. This database will be indexed on ChemSpider shortly. This database is generated from the conversion of a series of chemical names to chemical structures and has been performed in collaboration with Advanced Chemistry Development (ACD/Labs) using a number of their tools as detailed in a technical note posted at their site. ACD/Labs has also made the database available at their website in ChemFolder format. The database is available in SDF format by downloading the data from PubChem.

The database in question is a derivative work of a database downloaded in text file format from the U.S. Food and Drug Administration (FDA) site. ChemSpider has every intention to continue contributing such data back to the community on an ongoing basis and will post additional databases in the future.