Talk:Teriflunomide

Structure

Is the double bond really Z? I only found this structure on the web (Prous, ÖAZ, FreePatentsOnline (image), FreePatentsOnline (text)), but the formula on A77 1726 (seems to be deleted now) showed E. E also seems to be the natural outcome of the activation reaction. --ἀνυπόδητος (talk) 20:14, 10 September 2008 (UTC)

Teriflunomide might not be the same as A77 1726, contrary to Drugs of the Future. PubChem has

• an id 5479847 for teriflunomide (calling it the active metabolite of leflunomide) with a link to the MeSH entry on A77 1726
• and an id 16760239 for A77 1726 (which ís the active metabolite of leflunomide according to the Wikipedia article A77 1726).

I removed the references to the identity of teriflunomide and A77 1726 (on Leflunomide and Therapies under investigation for multiple sclerosis as well) --ἀνυπόδητος (talk) 17:16, 11 September 2008 (UTC)

According to rINN list 42, the double bond is Z, and the structure of teriflunomide corresponds to CID 5479847 from PubChem (nitrile, not isocyanide). Martindale also states: "After oral doses leflunomide undergoes first-pass metabolism to A771726 (teriflunomide)".[1] See also PMID 16979204, PMID 16142756, and [2]. Image:A77 1726.png was deleted from Commons by the uploader himself, Edgar181, as "incorrect chemical structure".

I think it's safe to say teriflunomide and A77 1726 are one and the same, and CID 16760239 from PubChem is incorrect. Fvasconcellos (t·c) 17:46, 11 September 2008 (UTC)

Chemical Abstracts lists teriflunomide and A 77-1726 as synonyms under CAS#163451-81-8 with structure and Z-geometry matching what's in the drugbox now. PubChem is error prone, so I wouldn't worry that one structure there doesn't match. This is why I changed the PubChem link in this article and deleted the original image I created Image:A77 1726.png which was based on that wrong PubChem listing. The issue of the double bond geometry is a minor point, in my mind. The E form will be the one produced by metabolism, but the structure will actually interconvert between the E/Z enolic forms and the corresponding keto-amide, with the Z enol being the most stable and therefore most predominant form. -- Ed (Edgar181) 20:14, 11 September 2008 (UTC)

I have taken a look at quite a few journal articles published on teriflunomide, including the Drugs of the Future review cited in the article. It is clear that the literature consistently treats teriflunomide and A 77-1726 as synonyms. I have therefore reverted the article back to one of Anypodetos' earlier versions. If anyone objects, please let me know. -- Ed (Edgar181) 20:35, 11 September 2008 (UTC)

Thanks for taking the trouble! I will revert Leflunomide and Therapies under investigation for multiple sclerosis as well. And thanks for reminding me of the enolic E/Z conversion thing - seems I'm forgetting chemistry... --ἀνυπόδητος (talk) 20:46, 11 September 2008 (UTC)

External links

I am quite new at editing. But I think it might be good to add some external links to this? such as [3] and perhaps [4] ? Don't want to stick them in refs —Preceding unsigned comment added by Hyperism (talk • contribs) 11:42, 22 November 2010 (UTC)

Hi! Instead of just adding external links, it would be better (but more work) to extract the interesting information from these pages and work them into the article. The ideal structure of a drug article is to be found at WP:MOSMED#Drugs; there it also says that "External link" sections are discouraged because they attract spam. Of course it is not mandatory to follow the structure given there, but it might help getting you started with the organisation of the text.

The links you gave could (and should) still be added afterwards, namely in the form of references. The overall effect would be that people get a single consistent text containing (ideally) all important information about the drug instead of clicking their way through a number of links. If anyone is in doubt whether a particular sentence is true, they can still click the reference to find out where the information is from.

If you need any help with editing, please don't hesitate to ask here. I am watching this page and will come back to your requests. Happy editing! --ἀνυπόδητος (talk) 14:04, 22 November 2010 (UTC)

Thank you! I guess the subject matter made me a bit nervous about adding content as it is medication and I know very little about it. I am just a person with MS with a big intrest in treatment! I'll have a go at reading those articles properly again and adding some content! Thanks for your help! —Preceding unsigned comment added by Hyperism (talk • contribs) 11:53, 23 November 2010 (UTC)

Yes, please just add anything worth noting. I'll help you with formatting if you want. In case you don't know already: It is generally not allowed to copypaste text into Wikipedia – try to rephrase what you want to tell our readers. Cheers, ἀνυπόδητος (talk) 17:07, 23 November 2010 (UTC)

Tenere trial

According to the FDA's clinicaltrials.gov website The Tenere Trial WAS NEVER POWERED to be a "Superiority" trial just a COMPARISON TRIAL. Here is the Official Verbage on TENERE from www.clinicaltrials.gov (FDA) -

Purpose Primary objective was to assess the effectiveness evaluated by the time to failure of two doses of teriflunomide in comparison to (NOT SUPERIOR TO) interferon beta-1a in patients with relapsing Multiple Sclerosis [MS]. Secondary objectives were: •To assess the effect of the two doses in comparison to interferon beta-1a on: ◦Frequency of relapses, ◦Fatigue, ◦Patient's satisfaction with treatment. •To evaluate the safety and tolerability of the two doses in comparison to interferon beta-1a. The study consisted of a core treatment period with a common end date defined as 48 weeks after randomization of the last participant, followed by an optional long-term extension treatment period until teriflunomide is commercially available in accordance with local regulations.

In contrast, The Gilenya TRANSFORMS study was a superiority study. The Primary Outcome of the Transforms Study was - "This study assessed the safety, tolerability, and efficacy of 2 doses of oral fingolimod versus interferon β-1a to reduce the frequency of relapses in patients with relapsing-remitting multiple sclerosis." Versus means to compete

Please make the correction. — Preceding unsigned comment added by 199.245.32.209 (talk) 17:19, 6 December 2013 (UTC)

Changed wording. Thanks for catching that. By the way, you can fix errors on Wikipedia yourself. Just be bold! Cheers --ἀνυπόδητος (talk) 07:50, 7 December 2013 (UTC)