Continuing the investigations of Fluvastatin

30 Jul

When I started to investigate Fluvastatin as an example of what’s present in different databases I thought it would be quite easy. Alas…not so…

The investigation got me as far as distinguishing different stereoforms in different databases and then asking the question is fluvastatin supposed to be the ACTIVE form of the compound or the trade name of the compound? i.e. Should the name apply only to the active stereoform or to what is shipped in the bottle? The answer appears to be… “yes”. It is both.

The World Health Organization (WHO) lists in their International Nonproprietary Name for fluvastatin the form as shown in the image below.

The representation of Fluvastatin according to its INN

So according to the WHO fluvastatin is an enantiomeric  pair, so the (3R,5S,6E) and (3S,5R,6E) pair. This coincides with the marketed drug form as on Dailymed here. This does not agree with what is listed on Wikipedia   which shows the “active” stereoisomer.

So, I think the answer is “yes” it is both the marketed drug form as well as the active form. That makes retrieval of EXPLICIT answers from database searches difficult. What would you expect as a user if you searched on Fluvastatin? Both answers to show up?


About tony

Antony (Tony) J. Williams received his BSc in 1985 from the University of Liverpool (UK) and PhD in 1988 from the University of London (UK). His PhD research interests were in studying the effects of high pressure on molecular motions within lubricant related systems using Nuclear Magnetic Resonance. He moved to Ottawa, Canada to work for the National Research Council performing fundamental research on the electron paramagnetic resonance of radicals trapped in single crystals. Following his postdoctoral position he became the NMR Facility Manager for Ottawa University. Tony joined the Eastman Kodak Company in Rochester, New York as their NMR Technology Leader. He led the laboratory to develop quality control across multiple spectroscopy labs and helped establish walk-up laboratories providing NMR, LC-MS and other forms of spectroscopy to hundreds of chemists across multiple sites. This included the delivery of spectroscopic data to the desktop, automated processing and his initial interests in computer-assisted structure elucidation (CASE) systems. He also worked with a team to develop the worlds’ first web-based LIMS system, WIMS, capable of allowing chemical structure searching and spectral display. With his developing cheminformatic skills and passion for data management he left corporate America to join a small start-up company working out of Toronto, Canada. He joined ACD/Labs as their NMR Product Manager and various roles, including Chief Science Officer, during his 10 years with the company. His responsibilities included managing over 50 products at one time prior to developing a product management team, managing sales, marketing, technical support and technical services. ACD/Labs was one of Canada’s Fast 50 Tech Companies, and Forbes Fast 500 companies in 2001. His primary passions during his tenure with ACD/Labs was the continued adoption of web-based technologies and developing automated structure verification and elucidation platforms. While at ACD/Labs he suggested the possibility of developing a public resource for chemists attempting to integrate internet available chemical data. He finally pursued this vision with some close friends as a hobby project in the evenings and the result was the ChemSpider database ( Even while running out of a basement on hand built servers the website developed a large community following that eventually culminated in the acquisition of the website by the Royal Society of Chemistry (RSC) based in Cambridge, United Kingdom. Tony joined the organization, together with some of the other ChemSpider team, and became their Vice President of Strategic Development. At RSC he continued to develop cheminformatics tools, specifically ChemSpider, and was the technical lead for the chemistry aspects of the Open PHACTS project (, a project focused on the delivery of open data, open source and open systems to support the pharmaceutical sciences. He was also the technical lead for the UK National Chemical Database Service ( and the RSC lead for the PharmaSea project ( attempting to identify novel natural products from the ocean. He left RSC in 2015 to become a Computational Chemist in the National Center of Computational Toxicology at the Environmental Protection Agency where he is bringing his skills to bear working with a team on the delivery of a new software architecture for the management and delivery of data, algorithms and visualization tools. The “Chemistry Dashboard” was released on April 1st, no fooling, at, and provides access to over 700,000 chemicals, experimental and predicted properties and a developing link network to support the environmental sciences. Tony remains passionate about computer-assisted structure elucidation and verification approaches and continues to publish in this area. He is also passionate about teaching scientists to benefit from the developing array of social networking tools for scientists and is known as the ChemConnector on the networks. Over the years he has had adjunct roles at a number of institutions and presently enjoys working with scientists at both UNC Chapel Hill and NC State University. He is widely published with over 200 papers and book chapters and was the recipient of the Jim Gray Award for eScience in 2012. In 2016 he was awarded the North Carolina ACS Distinguished Speaker Award.

Posted by on July 30, 2012 in Data Quality


2 Responses to Continuing the investigations of Fluvastatin

  1. Chris Evelo

    July 31, 2012 at 2:51 am

    Yes, I would expect both answers to show up. Depending on what I was doing I would use either one or the other. Simply put, for pharmacological work I would use mainly the active component. Not only though because the other one could actually be causing the other effects like having some antiviral activity. As a toxicologist I would have to take both into account.

    That actually brings me on a side track. I remember professor Ariens, head of the Pharmacology department in Nijmegen when I was there at an early stage in my career. He was always on a crusade to saying the two should be the same. It is a bad idea to add a pharmacological inactive stereoisomer to an active drug. After all that inactive compound could well cause side effects. He pushed the ideas that drugs should be stereochemically purified decades ago. And I think he was right.

  2. Eddie Kehoe

    August 3, 2012 at 8:55 pm

    As a patent searcher covering a range of ‘chiral’ drugs – the thought of using an ‘explicit’ search would mean I would miss a lot of patent documents. Because a lot of patent specifications show structures as racemic compounds – unless the specification is particularly concerned with the ‘chiral’ aspect! I would want to see ALL fluvastatin answers and worry about the chirality later. Some patent specifications have wrong names and wrong structures!


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