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.


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.


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!



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.

Stumble it!

10 Responses to “InChIs and SMILES from Erectile Dysfunction Drug Searches at ChemSpider”

  1. David Bradley says:

    This post takes the ChemSpider experience to a whole new level and does for ED drugs what Paul May’s Silly Molecules does for cummingtonite and arsole. Poor Layla from Belgium, though, maybe we should hear her tortured Skyping tale, or if she was searching with ED in mind, maybe not.


  2. Will says:

    Well, I got this the other day:

    “Hi, I’m looking for the chemical way to extract cocaine from coca leaves and create the drug in question.”

    Oh, OK.


  3. David Bradley says:

    No need, you could (until this week) buy cocaine in a can – http://www.chemspider.com/chemistry-news/cocaine-in-a-can.html – I suspect there will be a few cans of this stuff left on shelves until at least Friday.

  4. Steve Gerard's Bremelanotide Bulletin says:


    I author the “Bremelanotide Bulletin” and just wanted to pop by to let you and your readers know the results of Bremelanotide Phase IIb trials will be presented at the American Urological Association’s annual meeting that takes place May 19 to the 24th…

    The Bremelanotide specific presentations will be on the 21st and include: “Phase 2b Study of Bremelanotide in the Treatment of ED in Non-Diabetic Males” with another presentation later that afternoon for Phase 2b results involving Diabetic Males with ED.

    The other earlier (~1pm) presentation is “Improvement in Sexual Relationship Satisfaction, Confidence, and Self- Esteem in ED Patients Treated with Bremelanotide”.

    Most are expecting very favorable results to be announced.


    - Steve Gerard

  5. Antony Williams says:

    666 – The Number of the Beast – and the Beast is Created By a Drug

    “Let him that hath understanding count the number of the beast: for it is the number of a man; and his number is Six hundred threescore and six.” What on earth does this quote from the Book of Revelations have to do with Drugs? Well, following on from the recent posting regarding erectile dysfunction drugs it has been pointed out that Viagra may indeed be part of the devils’ work in creating Beasts from Men. The nominal mass of Viagra, sildenafil citrate is 666 Daltons. Ah yes…and men shall become beasts….

  6. Andrew Anderson says:

    I can’t help but comment:
    I understand that metabolites of prodrugs are more “effective.” So the size InChI doesn’t necessarily means everything…

    I won’t bring down the blog any more by bringing up ships/oceans or wands/wizards, will I?

  7. David Bradley says:

    Nominal indeed Tony! With the citrate it is 666.6999 D, but there’s a kind of asymmetric rotational symmetry in that too with those three nines …

    Meanwhile, Stevee Gerhard’s comment reminded me, I wrote about Bremelanotide, time for an update.

  8. Antony Williams says:

    Now viagra is being touted for helping to cure jet-lag too. See David’s posting on Spinneret at http://www.chemspider.com/chemistry-news/cure-jet-lag-join-the-mile-high-club.html

  9. ChemSpider Blog » Blog Archive » The InChI Has is Unveiled - and now there are 17.6 MILLION of them online says:

    [...] dyscfunction and how the size of the InChI does give a bigger SMILES in general. This IS an R-rated blog-posting so maybe not… Now, with the InChI key all of these issues will be resolved for different [...]

  10. Erectile Dysfunction says:

    You may be interested in IEDR’s (Institute for Erectile Dysfunction) new resource website called Erectile Dysfunction Central. The site is a research and news portal for erectile dysfunction. Currently the site hosts a database of 11k+ research abstracts on ED. The site also aggregates research and news on viagra, cialis, and levtitra.

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