Talk:Paclitaxel

message: I added the nomenclature section from the Paclitaxel total synthesis article because it seems more relevant here. Hansonrstolaf (talk) 12:32, 6 March 2009 (UTC)
thread_title: Nomenclature

message: Several reference sources are given more than one number in the reference list.  Using different pages in Goodman and Walsh does not require it to be referenced fifteen separate times.  There is no reason for Jo Whelan's paper to be given three different citation numbers.  —Preceding unsigned comment added by 138.38.154.172 (talk) 15:01, 25 February 2009 (UTC)
thread_title: References

message: Peter Wiernik, M.D. a medical oncologist then at the Albert Einstein Cancer Center devised a method for preventing most of the anaphylactoid reactions to the drug, and thereby saved the drug from extinction and allowed clinical development to continue. He also published the earliest human pharmacokinetic studies of the drug.
: An anonymous user added the above paragraph but managed to insert it between a different statement and its reference source so it appeared incorrectly to be sourced. Given that, and lack of any detail on what the 'anaphylactoid reactions' are or when this 'saving the drug from extinction' occurred, I have parked this on the talk page until someone can provide properly referenced detail. Js229 11:26, 10 September 2007 (UTC)
replies: text: Will look into it.  Le Prof  Leprof 7272 (talk) 22:41, 30 May 2014 (UTC)
thread_title: Wiernik

message: I have read that Taxol can be produced also from a shrub common in Eastern Canada called ground hemlock or eastern yew (Taxus canadensis). See Natural resources Canada and CBC news. Is the drug produced from shrubs cheaper/simpler/higher quality than the drug produced by fermentation? Brona 15:33, 6 Jul 2004 (UTC)
replies: text: In Biotechnology: An Introduction 2ed () on page 128, the last line of a table labeled Some Pharmaceutical Products Manufactured Using Recombinant DNA Technology reads: Taxol - Plan product used for treatment of ovarian cancer; produced by E. coli. However, this doesn't seem correct considering the other reading I have done. Can anybody confirm if paclitaxel has ever been produced by E. coli? 70.237.144.179 07:27, 4 June 2007 (UTC)
thread_title: Other sources of paclitaxel

message: St. Petersburg Times November 8, 2004:"
The St. Petersburg Times recently asked two University of South Florida professors to read a few Wikipedia articles on topics in their expertise. Chemistry professor Bill Baker said he was surprised at the amount of technical knowledge posted on the site, but said he found several small errors. 'The cancer drug Taxol, for example, is not produced by microbial fermentation.'
'That bothers me,' Baker said of the errors. 'I think that even if 99 percent of your facts check out, it is a disservice to promulgate 1 percent inaccuracies.'"
Probably out of date but just posting just in case.
lots of issues  | leave me a message 08:30, 24 May 2005 (UTC)
replies: text: . Also, your signature is confusing! JFW | T@lk 12:51, 24 May 2005 (UTC)
replies: text: It still says this, but is cited. Huh?----occono (talk) 09:26, 28 August 2009 (UTC)
thread_title: St. Petersburg Times 

message: I have put the license on the past tense as per Bristol Myers Squibb and replaced many Taxols with paclitaxels.  Please revert if I'm wrong. Rich Farmbrough 21:30, 8 October 2005 (UTC)
thread_title: License and name

message: I'd say the structure of taxol isn't "extremely" complex... it certainly is complex, yes, but the adjective "extremely" would suit more a molecule like Maitotoxin.
:I disagree.  Maitotoxin is actually simpler than Taxol, since it has a quasirepetitive motif with only a small set of functional groups.  However, judgement calls like that don't belong in wikipedia. —The preceding unsigned comment was added by 137.131.130.118 (talk) 10:23, 8 February 2007 (UTC)
replies: text: The "crystal structure" given as a figure (reference 4) is not, in the traditional sense, a crystal structure obtained through typical single-crystal x-ray diffraction methods. This is because paclitaxel doesn't form good single crystals for traditional methods of analysis.  In fact, there is only one known crystal structure of paclitaxel [D.  Mastropaolo, A.  Camerman, Y.  Luo and G.D.  Brayer, Proc.  Natl.  Acad.  Sci.  USA, 1995, 92, 6920-6924. ] This contains two molecules per asymmetric unit and crystallizes in the P21 space group. This form shared characteristics of the "polar" form predicted for paclitaxel. Unfortunately, the crystal also contains the toxic solvent dioxane and, therefore, isn't useful for studies in vivo. Because paclitaxel's bioactivity is strongly linked with its conformation, structural studies are extremely important for this molecule. E heider 01:12, 8 August 2007 (UTC)
replies: text: What is the perceived point, of the impact on utility, of an adventitious dioxane molecule co-crystallizing with paclitaxel in the study you report (i.e., the basis for saying "the crystal… isn't useful for studies in vivo)? This seems a fantastically important study, with broad, significant impact on therapeutic use of the molecule and its analogs—insofar it unequivocally confirms the structure and stereochemistry derived via synthesis and NMR spectroscopy. Non?  Le Prof  Leprof 7272 (talk) 23:27, 30 May 2014 (UTC)
thread_title:  Structure 

message: Mostly spelling, capitalization, paragraph structure, readability, etc.  However, clarification of various Taxus species and uses, with new info on current production methods.  Thanks!
Dcwest 19:35, 19 February 2007 (UTC)
thread_title:  Updates 

message: See this press release.
:Pierre Potier’s team also invented a process to produce, in unlimited quantity, a substance previously discovered in the United States, called TAXOL®, and made of yew bark extract. Thanks to the discovery by the Gif-sur-Yvette researchers of a precursor of Taxol® in local yew leaves, it is no longer necessary to cut down yew trees in order to make the drug.
CNRS is a fairly serious institution, so I'm inclined to believe them. I'm told that the patents over the production of Taxol and Taxotere are their first two patents in terms of income. This should surely be mentioned in the "production" section. David.Monniaux 10:59, 12 July 2007 (UTC)
replies: text: I will look to see how their contributions can be substantiated independently, and so appear here.  Cheers.  Le Prof  Leprof 7272 (talk) 23:20, 30 May 2014 (UTC)
thread_title:  Pierre Potier 

message: Is this considered a chemo drug?
:The term 'chemotherapy' actually refers to any type of drug-related therapy, irregardless of disease state. However, in recent years, it has become associated with cancer drug therapies by most laypeople. Dr. Cash 02:43, 29 September 2007 (UTC)
thread_title:  Cruious 

message: ACETYLOXY IS  ETHANOILOXY ?  —Preceding unsigned comment added by 89.77.15.69 (talk) 02:42, 15 September 2007 (UTC)
thread_title:  IUPAC 

message: Please visit the blog posting I made tonight
http://www.chemspider.com/blog/?p=168
I cannot put into this email since there are a lot of graphics to consult.
Here's the bottom line for Taxol on Wikipedia.
I can confirm at this point the CAS Number is correct in Wikipedia.
I can confirm the structure on Wikipedia IS Correct. 
The link to the PubChem record is to an INCORRECT structure and should be edited to link to CID:5147169.
The name should be 
IUPAC:    (1R,2R,3S,4R,7S,9R,10R,12S,15R)-4,12-Diacetoxy-15-{[(2S,3R)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl rel-benzoate
or 
CAS Index:
benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-  —Preceding unsigned comment added by 24.162.249.146 (talk) 01:55, 28 September 2007 (UTC)
replies: text: Hi Antony—I've fixed the PubChem accession number. As for the IUPAC name...which is most adequate? I'd like to see further input on this. As an aside, anyone can edit Wikipedia, you know—wouldn't you like to join? :) Fvasconcellos (t·c) 02:51, 28 September 2007 (UTC)

text: Hi..I tried editing the DrugBox and couldn't so assumed it was locked. Only to discover that I hadn't logged in...oops. Sorry, I would have done it myself. I have pasted the new IUPAC Name in:
(1R,2R,3S,4R,7S,9R,10R,12S,15R)-4,12-Diacetoxy-15-{[(2S,3R)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl rel-benzoate
I hate the fact that I have introduce spaces to not expand the Drug Box--Tony27587 13:36, 1 October 2007 (UTC)
thread_title:  Taxol Drug Box issues. 

message: Please do not revert the edit to which this Talk section refers , paragraph 3 of lede; rather, refute soundly the following arguments made with regard to POV and article accuracy issues, beforehand. (On unexplained reversion, I will elevate immediately for administrative review. Since this relates to two living chemists, I am treating this as, in essence, a BLP issue.) 
The lede sentence mentioning only the Holton group in the synthesis of paclitaxel is being edited for the following reasons:
*use of the word "notable" is unacceptable at Wikipedia with regard to discussing individual accomplishments, apart from reporting use of the word, about an individual, by others; it is specifically listed as an example of puffery, and is forbidden at WP:PEA, see , and its use here is just that, absent a citation using the term;
*to list only the Holton group, whose article was first to be accepted for publication, and not list the Nicolaou group, whose article was first to be published, when both appeared essentially simultaneously in 1994, and to do so when other areas of reporting and Wikipedia represent the accomplishments as comparable and simultaneous (see further below), is to to represent history in a biased manner; compare the third paragraph of the lede, here, to the following (from elsewhere in Wikipedia):
:
*in doing the foregoing, to further exclude mention of the ferment of broad paclitaxel synthetic activity taking place concurrently with the profound efforts of these two groups—this choice, alongside the "notable" wordchoice and the Nicolaou omission, further support the conclusion that the current description in the lede misrepresents the history of the period;
*to do so when other Wikipedia articles  and the remainder of this article  do not do so, reinforces the point;
*these points are all the more critical, given that this is both a high profile article, and the point-article for a series of articles on this natural product and on its activities; and finally
*to limit mention to one research team is to contradict the preponderance of scientific reporting, including from the most prominent American scientific news source,  where the report of this matter, appearing in Science, by Flam, is entitled "Race to synthesize taxol ends in a tie." See .
I am therefore editing the relevant sentence in the lede to reflect a substantiated, POV-neutral perspective, as it appears already within Wikipedia (e.g., here: ), without in any way marginalizing the important and fine work of the Holton group. This edit removes the critical POV issue, better reflects the remainder of the article and related articles at WP, and makes the text neutral with regard to this exciting chapter in natural products total synthesis.  
Note/disclaimer (a la Nature Publishing Group requirements): I have trained under none of the fine synthetic chemists now named in this revision of the article, have sat on faculty or boards with none, have consulted alongside none, but have done so under and alongside their peers, and have otherwise studied and taught their work (since 1990). See my User page (click on Edit to ungrey) if you have questions as to my credentials and expertise, with regard to making this edit.
Le Prof  Leprof 7272 (talk) 22:39, 30 May 2014 (UTC)
thread_title:  Contentious edit being broadcast (possible BLP and POV issue)  

message: … fully referencing the new section, and making it essentially neutral based on the sources.  (In the Production section, the TS material was a diversion, and confusing as to the point; as now is noted and cited, TS was never seen as a means to production.)  With this change, the lede mention of the Holton paclitaxel TS is now ready to appear as a summary statement of the neutral text that appears later in the text (to be done soon).
Also done with this edit: removed all red wikilinks, fixed a "cite error" problem (in earlier reference 27, see next action), added various citation tags in the production section (!), and touched up the closing BMS section vis-a-vis quotations and reference to the naming of Taxol® and its being assigned paclitaxel as an INN.
Discuss changes here, please.  (I will seek immediate admin involvement if there is a reversion without discussion.)   Le Prof Leprof 7272 (talk) 17:29, 2 June 2014 (UTC)
thread_title:  Total synthesis material separated from Production section 

message: The coverage of endophyte production in the section "Commercially viable paclitaxel production" contradicts in its conclusion the conclusion implied in the lede about the same matter.  Needs to be reconciled, changing one or the other.  (The lede cannot be cock sure positive, while the body of the article is ambivalent in conclusion.)  Le Prof Leprof 7272 (talk) 02:13, 3 June 2014 (UTC)
thread_title:  Contradiction between lede and later section tagged 

message: The announcement of intent to edit the lede vis-a-vis its ongoing POV issue, see , has been available here and has been without comment for over three weeks now. The issue of the contradiction between lede and text body on fungal production of paclitaxel has also been posted for this much time. As a result of the lack of any rebuttal or discussion, I am making the edit to the lede this morning, to remove the POV issue and to make the lede fully consistent with the body of the text. (Given the due diligence taken in addressing this potentially controversial edit, and the lack of any interest on anyone's part over these weeks, I will respond to a reversion with immediate request for Administrator attention.) Cheers, hope this closes this odd, longstanding lede issue.  Le Prof  Leprof 7272 (talk) 14:31, 24 June 2014 (UTC)
thread_title: Editing lede today

message: How are these images truly relevant to the section in which they appeared? (Where do we say that yew bark is used in the production of the precursor of paclitaxel?) What is the point of the emphasis on easily renewable yew needle and possible culture sources, if we are going to illustrate the production section with bark stripping? 
What in fact is the actual current biomaterial used in production, and is use of these images misleading to actual process? Since I cannot provide immediate sources, I am not answering my own questions. Neither should the images be reintroduced, unless sources are placed that make clear they are truly related to the Section (how paclitaxel is actually produced), and not fanciful, theoretical associations with the topic. Le Prof 73.210.155.96 (talk) 12:08, 13 March 2017 (UTC)
replies: text: The first sentence says this was how it used to be made.. Doc James (talk · contribs · email) 17:35, 13 March 2017 (UTC)
thread_title: Moved images to Talk for duscussion

message: Hello fellow Wikipedians,
I have just modified 4 external links on Paclitaxel. Please take a moment to review my edit. If you have any questions, or need the bot to ignore the links, or the page altogether, please visit this simple FaQ for additional information. I made the following changes:
*Added archive https://web.archive.org/web/20050526050715/http://www.fda.gov/cder/foi/label/2005/021660lbl.pdf to http://www.fda.gov/cder/foi/label/2005/021660lbl.pdf
*Added  tag to http://findarticles.com/p/articles/mi_m1295/is_n2_v57/ai_13417481
*Added archive https://web.archive.org/web/20120315095242/http://mssociety.ca/en/research/PT991213.htm to http://mssociety.ca/en/research/PT991213.htm
*Added archive https://web.archive.org/web/20120315095318/http://mssociety.ca/en/research/PT020227.htm to http://mssociety.ca/en/research/PT020227.htm
*Added archive https://web.archive.org/web/20050606012941/http://www.research.fsu.edu/researchr/fall2002/taxol.html to http://www.research.fsu.edu/researchr/fall2002/taxol.html
When you have finished reviewing my changes, you may follow the instructions on the template below to fix any issues with the URLs.
Cheers.—InternetArchiveBot (Report bug) 05:50, 24 May 2017 (UTC)
thread_title:  External links modified 

message: Hello fellow Wikipedians,
I have just modified one external link on Paclitaxel. Please take a moment to review my edit. If you have any questions, or need the bot to ignore the links, or the page altogether, please visit this simple FaQ for additional information. I made the following changes:
*Added archive https://web.archive.org/web/20070927005318/http://www.sciencepub.org/nature/0202/09zhao.pdf to http://www.sciencepub.org/nature/0202/09zhao.pdf
*Added  tag to http://www.biocon.com/docs%5CPress_Release_Q2_%2008_09.pdf
When you have finished reviewing my changes, you may follow the instructions on the template below to fix any issues with the URLs.
Cheers.—InternetArchiveBot (Report bug) 21:17, 26 July 2017 (UTC)
thread_title:  External links modified