View source for Talk:Paclitaxel

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==Nomenclature==
I added the nomenclature section from the [[Paclitaxel total synthesis]] article because it seems more relevant here. [[User:Hansonrstolaf|Hansonrstolaf]] ([[User talk:Hansonrstolaf|talk]]) 12:32, 6 March 2009 (UTC) 
==References==
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.  <span style="font-size: smaller;" class="autosigned">—Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[Special:Contributions/138.38.154.172|138.38.154.172]] ([[User talk:138.38.154.172|talk]]) 15:01, 25 February 2009 (UTC)</span><!-- Template:UnsignedIP --> <!--Autosigned by SineBot-->

==Wiernik==
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. [[User:Js229|Js229]] 11:26, 10 September 2007 (UTC)
::Will look into it.  Le Prof  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 22:41, 30 May 2014 (UTC)

==Wikipedia is great==

I was happy to see this article in the Wikipedia and delighted to be able to add a bit more information about Taxol's discoverers.  I work at RTI and know Drs. Wall and Wani.  Glad to be able to get them some Wikipedian recognition. [[user:SteveSmith|SteveSmith]]

Thanks for your contributions! Man, Wikipedia is awesome -- a little over an hour after my original submission, someone who knows the creators of Taxol adds some very useful information on it. [[User:maveric149]]


==Other sources of paclitaxel==

I have read that Taxol can be produced also from a shrub common in Eastern Canada called ground hemlock or eastern [[Taxus|yew]] (Taxus canadensis). See [http://www.atl.cfs.nrcan.gc.ca/index-e/what-e/science-e/nontimberforestproducts-e/ground_hemlock-1e.htm Natural resources Canada] and [http://www.cbc.ca/stories/2004/07/06/hemlock_rustlers040706 CBC news]. Is the drug produced from shrubs cheaper/simpler/higher quality than the drug produced by fermentation? [[User:Brona|Brona]] 15:33, 6 Jul 2004 (UTC)

:In ''Biotechnology: An Introduction 2ed'' ({{ISBN|9780495112051}}) 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? [[User:70.237.144.179|70.237.144.179]] 07:27, 4 June 2007 (UTC)

==Problem with Zhao paper reference and production in ''Nodulisporium''==

In 1993 it was discovered that taxol was also produced in a newly described fungus living in the yew tree, see: Stierle, A., G. Strobel, et al. (1993). "Taxol and Taxane Production by Taxomyces-Andreanae, an Endophytic Fungus of Pacific Yew." Science 260(5105): 214-216. It has since been found in a number of other endophytic fungi, some from other yews, some not; search [http://portal.isiknowledge.com/portal.cgi?DestApp=WOS&Func=Frame Web of Science] for "taxol and fungi" and you'll get a bunch of hits. Unfortuately, searching for "taxol and ''Nodulisporium''" turns up nothing, not even the article cited here, from "Nature and Science" which I submit is a junk journal for the following reasons: the name is an amalgam of the two biggest journals, it doesn't show up on Web of Science or the CA Digital Library database, and the translation is atrocious.

Finally, the assertion that taxol is produced commercially in  cultures of ''Nodulisporium'' is not even supported by the citation. The paper deals with the regeneration of fungal protoplasts, a tool used in genetic engineering of fungi. The study concludes that this is difficult to do with ''Nodulisporium'', and suggests ways to improve the process. Even if ''Nodulisporium'' does make taxol, that's a long way from it being a commercial production strain. From what I've been able to find taxol is commercially produced using plant cell culture from another species of yew, ''Taxus baccata''. --[[User:DLuber1|DLuber1]] 17:37, 6 August 2007 (UTC) -DL

:Update: I followed the link at the top to check out the Pharmacology workgroup and joined, but after mousing around it looks like a pretty moribund group, despite the good looking top page: e.g. Announcements, Peer Review, Proposals, Votes and Surveys, Help Requests, Tasks that need attention, Article Worklist and Collaboration of the Month all have little or no content. I'm new to all this so maybe I'm missing something. Anyway, I don't know the ettiquette for editing pages, I figured I'd post something at the workgroup but it looks like nobody's home, so I'll note here that I think this entry needs correction, and if the original author or anyone else doesn't object in a few weeks I'll remove the Zhao reference and incorporate my comments and references. -DL --[[User:DLuber1|DLuber1]] 18:27, 7 August 2007 (UTC)

:::No need to wait I think. The whole discussion of past, present, and possible synthesis routes needs work. Be bold and put in what you've found. But the paper does say the 'taxol-producing fungus' and there look like a couple of papers in the reference list that might support that so I would suggest it is better to leave in something like 'there are claims that a fungus can be used to produce taxol (ref) but there seems be little practical application reported in the scientific literature ' after the main discussion about PCF. I'd like to see some discussion of the history of PCF development while you're at it :) [[User:Js229|Js229]] 21:59, 7 August 2007 (UTC)

::::There's something genuinely interesting going on here...  Looking at {{PMID|19996685}} (Gliocladium sp.), {{PMID|19809969}} and {{PMID|7494141}} and {{PMID|8097061}} (Taxomyces andreanae), {{PMID|19762199}} (Botryodiplodia theobromae), {{PMID|19486395}} (Aspergillus niger), {{PMID|19484305}} (Cladosporium cladosporioides), {{PMID|19484278}} (Metarhizium anisopliae and others), {{PMID|19484278}} (Aspergillus candidus), {{PMID|19235515}} ("Mucor rouxianus sp."), {{PMID|19234679}} (Chaetomella raphigera), {{PMID|19067652}} (Phomopsis), {{PMID|18998547}} (Pestalotiopsis pauciseta), {{PMID|18254723}} (Pestalotiopsis terminaliae), {{PMID|10931912}} and {{PMID|8760934}} and {{PMID|8932715}} and {{PMID|9383479}}(Pestalotiopsis microspora), {{PMID|18652289}} (Aspergillus fumigates), {{PMID|11458463}} (Sporormia minima, Trichothecium sp., and an unidentified dimorphic fungus), {{PMID|11111032}} (Tubercularia sp.) The co-culture idea is apparently ongoing: {{PMID|19172266}}, {{PMID|18996212}}, {{PMID|11398918}}.  

::::Now from all this it's clear that there's one huge variety of bark fungi that produce this very, very odd looking molecule.  A strange explanation I saw was that the endophytes "mimic the host biochemical diversity" - while I suppose you can make an evolutionary-arms-race argument to say why this should be so, it still seems hard to swallow.  The fungi apparently require precursors: [[sodium benzoate]], [[sodium acetate]], [[biotin]], [[pyridoxal]], and [[L-phenylalanine]] to assemble the taxol.  It looks like about half of the biosynthetic pathway has been traced to yew genes [http://www.pnas.org/content/99/14/9166.long] so I can't blame it all on [[nanobacteria]] or fairies... I just don't understand why this molecule is made by so many different organisms. [[User:Wnt|Wnt]] ([[User talk:Wnt|talk]]) 23:05, 28 March 2010 (UTC)

:::::Thank you for this, Wnt! If you come across a good secondary reference, let us know.  Le Prof  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 23:32, 30 May 2014 (UTC)

==St. Petersburg Times ==
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.

[http://en.wikipedia.org/wiki/User:Lotsofissues lots of issues]  | [http://en.wikipedia.org/w/index.php?title=User_talk:Lotsofissues&action=edit&section=new leave me a message] 08:30, 24 May 2005 (UTC) 

:<nowiki>{{Sofixit}}</nowiki>. Also, your signature is confusing! [[User:Jfdwolff|JFW]]&nbsp;|&nbsp;[[User_talk:Jfdwolff|<small>T@lk</small>]] 12:51, 24 May 2005 (UTC)
::It still says this, but is cited. Huh?----[[User:Occono|<span style="color:orange;">occono</span>]] ([[User talk:Occono|talk]]) 09:26, 28 August 2009 (UTC)

==License and name==
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. ''[[User:Rich Farmbrough|Rich Farmbrough]]'' 21:30, 8 October 2005 (UTC)

== Structure ==

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]].{{who?}}

: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. <small>—The preceding [[Wikipedia:Sign your posts on talk pages|unsigned]] comment was added by [[Special:Contributions/137.131.130.118|137.131.130.118]] ([[User talk:137.131.130.118|talk]]) 10:23, 8 February 2007 (UTC).</small><!-- HagermanBot Auto-Unsigned -->

::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. [[User:E heider|E heider]] 01:12, 8 August 2007 (UTC)

:::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  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 23:27, 30 May 2014 (UTC)

== Updates ==

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

== Pierre Potier ==

See [http://www.cnrs.fr/cw/en/pres/compress/mistpotier.html 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. [[User:David.Monniaux|David.Monniaux]] 10:59, 12 July 2007 (UTC)

: I will look to see how their contributions can be substantiated independently, and so appear here.  Cheers.  Le Prof  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 23:20, 30 May 2014 (UTC)

== Cruious ==

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. [[User:Derek.cashman|Dr. Cash]] 02:43, 29 September 2007 (UTC)

== IUPAC ==

ACETYLOXY IS  ETHANOILOXY ?  <small>—Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[Special:Contributions/89.77.15.69|89.77.15.69]] ([[User talk:89.77.15.69|talk]]) 02:42, 15 September 2007 (UTC)</small><!-- Template:UnsignedIP --> <!--Autosigned by SineBot-->

== Taxol Drug Box issues. ==

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)-  <small>—Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[Special:Contributions/24.162.249.146|24.162.249.146]] ([[User talk:24.162.249.146|talk]]) 01:55, 28 September 2007 (UTC)</small><!-- Template:UnsignedIP --> <!--Autosigned by SineBot-->
: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? :) [[User:Fvasconcellos|Fvasconcellos]]<small>&nbsp;([[User talk:Fvasconcellos|t]]·[[Special:Contributions/Fvasconcellos|c]])</small> 02:51, 28 September 2007 (UTC)
: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--[[User:Tony27587|Tony27587]] 13:36, 1 October 2007 (UTC)

== Contentious edit being broadcast (possible BLP and POV issue)  ==

Please do not revert the edit to which this Talk section refers [https://en.wikipedia.org/wiki/Paclitaxel], 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 [https://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Words_to_watch#Puffery], ''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):
:{{quotation | "Another group, led by K.C. Nicolaou of the Scripps Research Institute, announced the complete synthesis of paclitaxel at the same time (in February 1994) as Holton's group at Florida State University. Holton argued that his technique was superior to Nicolaou because of the higher yield, whereas Nicolaou said that their yields would be similar if Holton had calculated the yield at every step instead of at an intermediate point of his synthesis." (referencing Flam, in ''Science'', see below; this directly from [https://en.wikipedia.org/wiki/Paclitaxel#Production].)}}
*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 [https://en.wikipedia.org/wiki/Paclitaxel_total_synthesis#Total_synthesis] and the remainder of this article [https://en.wikipedia.org/wiki/Paclitaxel#Production] 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 [http://www.ncbi.nlm.nih.gov/pubmed/7906053].

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: [https://en.wikipedia.org/wiki/Paclitaxel_total_synthesis#Total_synthesis]), ''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  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 22:39, 30 May 2014 (UTC)

== Non-independent source being moved from Production section to Talk ==

…until a suitable independent citation can be found to support the text content. The text content is presumed accurate, but it is being labeled by a {{cn}} tag, until a replacement is found. The non-independence of the cited article is asserted, as it is a university communications venue for FSU, a primary academic participant in the race to synthesize and semi synthesize paclitaxel, and the text statement it supports regards this race. Here is the reference removed, with its accompanying sentence (lead markup bracket removed):
*The view of the NCI, however, was that the CNRS route was not practical.  ref name="Stephenson_2003">{{cite journal|title=A tale of taxol|author=Stephenson, Frank|journal=Florida State University Research in Review|volume=12|issue=3|date=Fall 2003|url=http://www.rinr.fsu.edu/fall2002/taxol.html}}</ref>{{page needed}}
Please help find a suitable independent source for this statement, with page numbers; because the statement regards a claim of a position taken by a US government agency, its independent verification should be a straightforward matter.   Le Prof  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 14:32, 2 June 2014 (UTC)
::This had as a further result, another portion of text being without citation, to which a {{cn}} tag was also added:
::*"BMS took the process in-house and started to manufacture paclitaxel in Ireland from 10-deacetylbaccatin isolated from the needles of the European yew."
::Le Prof  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 17:40, 2 June 2014 (UTC)

== Total synthesis material separated from Production section ==

… 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 [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 17:29, 2 June 2014 (UTC)

== Contradiction between lede and later section tagged ==

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 [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 02:13, 3 June 2014 (UTC)

==Editing lede today==
The announcement of intent to edit the lede vis-a-vis its ongoing POV issue, see [https://en.wikipedia.org/wiki/Talk:Paclitaxel#Contentious_edit_being_broadcast_.28possible_BLP_and_POV_issue.29], 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  [[User:Leprof 7272|Leprof 7272]] ([[User talk:Leprof 7272|talk]]) 14:31, 24 June 2014 (UTC)

==Moved images to Talk for duscussion==
[[Image:PacificYew 8566.jpg|thumb|left|Undisturbed Pacific yew bark contains paclitaxel and related chemicals.]]

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? 

[[Image:Yew bark Taxol PD.jpg|thumbnail|right|The bark is peeled and processed to provide paclitaxel.]]

<br>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 [[Special:Contributions/73.210.155.96|73.210.155.96]] ([[User talk:73.210.155.96|talk]]) 12:08, 13 March 2017 (UTC)
::The first sentence says this was how it used to be made.. [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 17:35, 13 March 2017 (UTC)

==Wording==
Should we go with 

*"Use during pregnancy may result in harm to the '''fetus'''"
*"Use during pregnancy may result in harm to the '''baby'''"

As we are writing for a general audience and the two terms are used interchangeably in this content I support the use of baby. Others thoughts? [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 22:30, 3 May 2017 (UTC)
:What is the route of transmission? Your edit-summaries note "Yup the problem occurs in the baby when it is born." and "The negative affects are typically only noticed when the baby is born." The former statement is a little stronger--that whatever the drug does, it doesn't ''happen'' until birth, rather than happening in utero and remaining undetected until birth. Which ref actually supports the fetal/at-birth specific details, vs just that it is in Pregnancy Category D? [[User:DMacks|DMacks]] ([[User talk:DMacks|talk]]) 23:04, 3 May 2017 (UTC)
::The FDA uses "baby" not "fetus" for the med classification here[https://www.fda.gov/forconsumers/byaudience/forwomen/ucm118567.htm]. 
::CDC uses "unborn baby"[https://www.cdc.gov/pregnancy/meds/] [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 23:52, 3 May 2017 (UTC)
:I agree that the right choice might depend upon the kind of harm (e.g., stillbirth vs premature birth). 
:I always dislike using "the fetus" when we mean "the embryo" or "the future-baby at all developmental stages from conception through birth".  This drug likely affects all stages of development, but it's unwanted effects are worst in the first trimester.  As a result, I'd prefer "unborn baby" to "fetus".  It would also be appropriate to include some idea of what the harms are (premature birth or low birth weight; miscarriage or deformity if given during the first trimester[https://www.ncbi.nlm.nih.gov/pubmed/22907101]), and how common they are (not as common as you might think for cytotoxic chemotherapy[https://academic.oup.com/annonc/article/21/2/425/326965/Taxanes-for-breast-cancer-during-pregnancy-a], no worse than other options[https://www.ncbi.nlm.nih.gov/pubmed/22875836], 92% healthy babies[https://www.ncbi.nlm.nih.gov/pubmed/22907101]).  [[User:WhatamIdoing|WhatamIdoing]] ([[User talk:WhatamIdoing|talk]]) 02:59, 4 May 2017 (UTC)
::Thanks [[User:WhatamIdoing]] happy with "unborn baby" and will look at adding more details regarding harm to the body of the article. [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 03:18, 4 May 2017 (UTC)
:::That sounds reasonable. Including "unborn" avoids any possible implication that it is a "during delivery" effect (compare to major mode of mother->child HIV transmission) or a later effect involving nursing or child having some sort of withdrawal. [[User:DMacks|DMacks]] ([[User talk:DMacks|talk]]) 05:21, 4 May 2017 (UTC)
::::I would be cautious about use of "baby". Sure, call it an "unborn baby" at 8 months gestation, but in the first trimester, calling it a baby has an anti-abortion bias. [[NHS Choices]] tends to use "embryo" and "foetus" in its patient information, but does also use "baby"/"unborn baby" (although I couldn't find anything specifically on this drug). [[User:Bondegezou|Bondegezou]] ([[User talk:Bondegezou|talk]]) 09:22, 4 May 2017 (UTC)
:::::If this was being used in the context of abortion I would more understand the concern. But this is about potential complications of the use of this medication in pregnancy. [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 23:58, 4 May 2017 (UTC)
::::::agree w/ Doc James on this point--[[User:Ozzie10aaaa|Ozzie10aaaa]] ([[User talk:Ozzie10aaaa|talk]]) 14:53, 5 May 2017 (UTC)
::::::"This drug likely affects all stages of development, but it's unwanted effects are worst in the first trimester. As a result, I'd prefer "unborn baby" to "fetus"."  -How is "unborn baby" a better description during the first trimester than "fetus". That's not logical at all.  "Developing fetus" is what it is at that stage, and saying that would also reflect the fact that paclitaxel is causing abnormalities of development. It doesn't matter whether the context is abortion or not, saying "baby" would still affect how people think about it.[[Special:Contributions/188.29.165.33|188.29.165.33]] ([[User talk:188.29.165.33|talk]]) 12:12, 5 May 2017 (UTC)
:::::::According to [[Embryo]], {{tq|In humans, a pregnancy is generally considered to be in the embryonic stage of development between the fifth and the eleventh weeks after fertilization, and is expressed as a fetus from the twelfth week.}} Are fetus and baby truly used interchangeably? This is not the impression given by the article [[Infant]]. &bull; &bull; &bull; [[User:Pbsouthwood|Peter (Southwood)]] [[User talk:Pbsouthwood|<sup>(talk)</sup>]]: 16:19, 5 May 2017 (UTC)
::::::::The article [[Infant]] states {{tq|before birth, the term "fetus" is used}}. However if the developmental deformities from taxol occur mostly in the first trimester, that's actually an overlap between "fetus" and "embryo". So either 'developing embryo' or 'developing fetus' would be logical terms.   188.29.165.33  (can't sign normally, the IP keeps changing)
::::::::::Or we can use common English and simply stick with "unborn baby" [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 21:06, 7 May 2017 (UTC)
:::::::::::That phrase is the most biased; like saying 'it's unborn but it's a baby anyway'. That wording implies an advanced development, even though during most of the first trimester we're talking about, is a stage too early to even be called a 'fetus'.  188.29.165.33
:If we actually say what the effects are, we can reword to avoid this sentence structure altogether. For example, "use of paclitaxel during pregnancy is associated with an increased risk of [some symptom]". I'm having trouble finding anything though...the label says Pregnancy Category D, meaning there is evidence of risk, but only based on rat/rabbit studies and by extrapolation from its biochemical targets. Conversely, the label states that there are no controlled human studies. And a 2012 systematic review on human reports found no effect.[[doi:10.1093/annonc/mdp517]] [[User:DMacks|DMacks]] ([[User talk:DMacks|talk]]) 21:25, 7 May 2017 (UTC)
::Maybe say "use of paclitaxel during pregnancy may be associated with an increased risk of [some symptom]", because it's not been proven to happen in humans. Otherwise I agree.  188.29.165.33
:::This wording is more informative:  Animal studies suggest increased fetal demise, decreased birth weight and delayed ossification if used during pregnancy;<ref>[[doi:10.3109/00016349.2010.512070]]</ref><ref>[[doi:10.1111/IGC.0b013e3181fb18c8]]</ref> however a review suggests it is safe in humans during the 2nd/3rd trimester.<ref>[[doi:10.1093/annonc/mds170]]</ref>    "188.29.165.33"  <!-- Template:Unsigned IP --><small class="autosigned">—&nbsp;Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[Special:Contributions/92.40.248.12|92.40.248.12]] ([[User talk:92.40.248.12#top|talk]]) 17:31, 8 May 2017 (UTC)</small> <!--Autosigned by SineBot-->
::::The lead should provide an overview. There is not much evidence as it has not been well studied. rxlist states "It could harm the unborn baby."[http://www.rxlist.com/taxol-side-effects-drug-center.htm]
::::A specific discuss of the evidence should occur in the body of the article IMO.
::::The product monograph from the FDA website says "TAXOL can harm your unborn baby."[https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020262s049lbl.pdf] [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 04:18, 9 May 2017 (UTC)
::::::{{ping|Doc James}} It says 'baby' once, in the lay-speak "What should I tell my healthcare provider before receiving TAXOL?" section of the monograph. In comparison, the "Pregnancy" section uses 'fetus' once and 'fetal' three times. There's no real need to dumb it down. [[User:LeadSongDog|LeadSongDog]] <small>[[User talk:LeadSongDog#top|<span style="color:red; font-family:Papyrus;">come howl!</span>]]</small> 20:15, 10 May 2017 (UTC)
::::::::Maybe we use "baby" once in the lead. And use the more technical terms in the body. As a source for the general population there is nothing wrong with using common language rather than more technical language. [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 23:43, 10 May 2017 (UTC)
:::::::::It's not 'technical', it's accurate. Wikipedia is an encyclopedia, not a leaflet.[[Special:Contributions/92.40.249.102|92.40.249.102]] ([[User talk:92.40.249.102|talk]]) 00:39, 11 May 2017 (UTC)
::::::::::WP is a online encyclopedia written for a general audience yes. [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 
01:17, 11 May 2017 (UTC)
:::::::::::This doesn't mean Wikipedia should call a first-trimester fetus/embryo a 'baby' just to have 'common language'.  [[Special:Contributions/92.40.249.102|92.40.249.102]] ([[User talk:92.40.249.102|talk]]) 14:30, 11 May 2017 (UTC)
::::: These all repeat what the manufacturer's insert States. And they're all based on theoretical assumptions (edit: and animal studies). But the evidence in humans points mostly in a different direction. The sentence in the lead shouldn't be misleading. "188.29.165.33"  <!-- Template:Unsigned IP --><small class="autosigned">—&nbsp;Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[Special:Contributions/94.197.121.114|94.197.121.114]] ([[User talk:94.197.121.114#top|talk]]) 13:45, 9 May 2017 (UTC)</small> <!--Autosigned by SineBot-->
::::::The evidence in humans is nearly non existence as one is not allowed to do human trials in pregnant women unless animals studies are showing it is relatively safe. If animals studies show it likely is not human studies are nearly impossible to do. [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 01:45, 10 May 2017 (UTC)
:::::::The review did say it's relatively safe during the second and third trimester. If you don't like that, then say 'use during pregnancy may cause birth defects'. [[Special:Contributions/94.197.120.77|94.197.120.77]] ([[User talk:94.197.120.77|talk]]) 13:08, 10 May 2017 (UTC)
::::::::::Which review? Would be happy with "use during pregnancy may cause birth defects" [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 15:32, 11 May 2017 (UTC)
:::::::::::I didn't make it very clear; I was referring to https://www.ncbi.nlm.nih.gov/pubmed/22907101 - which two other users posted, one then describing it as "a 2012 systematic review on human reports found no effect."  <!-- Template:Unsigned IP --><small class="autosigned">—&nbsp;Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[Special:Contributions/5.148.17.228|5.148.17.228]] ([[User talk:5.148.17.228#top|talk]]) 18:55, 11 May 2017 (UTC)</small> <!--Autosigned by SineBot-->
Others thoughts on "use during pregnancy may cause birth defects"? Should we go with that? [[User:Doc James|<span style="color:#0000f1">'''Doc James'''</span>]] ([[User talk:Doc James|talk]] · [[Special:Contributions/Doc James|contribs]] · [[Special:EmailUser/Doc James|email]]) 22:19, 11 May 2017 (UTC)
:Crickets. Crickets everywhere. Since nobody human is saying anything I'll go ahead and insert that line.  [[Special:Contributions/188.29.165.59|188.29.165.59]] ([[User talk:188.29.165.59|talk]]) 12:58, 14 May 2017 (UTC)

{{reflist-talk}}

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== Optilume ==

Anybody want to add in use of paclitaxel in urethral stricture dilation balloons that prevent need for redilation, due I'd assume to similar effect as mentioned in the restenosis section when used in arterial dilation with stents?
[[Special:Contributions/2601:681:8E7F:F8A0:2597:7CF2:DCB8:12E1|2601:681:8E7F:F8A0:2597:7CF2:DCB8:12E1]] ([[User talk:2601:681:8E7F:F8A0:2597:7CF2:DCB8:12E1|talk]]) 21:51, 2 August 2024 (UTC)

:This is exactly what I came to this article to read about. As I may be getting this procedure done in the near future, I decided it would be due diligence to read some papers and discussion on the subject. It is a little disconcerting to not see it mentioned in this article. [[Special:Contributions/68.170.112.91|68.170.112.91]] ([[User talk:68.170.112.91|talk]]) 01:16, 10 March 2025 (UTC)

== Paclitaxel's appearance in the ''Brainy Baby'' website ==

In the [https://www.thebrainystore.com/collections/shop-brainy-baby?srsltid=AfmBOopuZ8uMkrWwMUJjDop88Gt-aegYt1VAMGfln957GV46hcK9vbWm official shop] in the ''Brainy Baby'' website, one of the drawings in the first picture features a molecule. The molecule that ''Brainy Baby'' used is actually the drawing of paclitaxel. [[User:BIG DADDY Dunkleosteus|BIG DADDY Dunkleosteus]] ([[User talk:BIG DADDY Dunkleosteus|talk]]) 13:10, 27 May 2025 (UTC)