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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)
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)
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.
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. 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
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)
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 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. -- DLuber1 17:37, 6 August 2007 (UTC) -DL
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)
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)
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?
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)
See this press release.
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)
Is this considered a chemo drug?
ACETYLOXY IS ETHANOILOXY ? —Preceding unsigned comment added by 89.77.15.69 ( talk) 02:42, 15 September 2007 (UTC)
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)
(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)
Please do not revert the edit to which this Talk section refers [2], 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:
"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 [4].)
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: [8]), 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)
…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 citation needed 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):
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 Leprof 7272 ( talk) 14:32, 2 June 2014 (UTC)
… 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)
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)
The announcement of intent to edit the lede vis-a-vis its ongoing POV issue, see [9], 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)
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)
Should we go with
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? Doc James ( talk · contribs · email) 22:30, 3 May 2017 (UTC)
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. • • • Peter (Southwood) (talk): 16:19, 5 May 2017 (UTC)
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)
01:17, 11 May 2017 (UTC)
Others thoughts on "use during pregnancy may cause birth defects"? Should we go with that? Doc James ( talk · contribs · email) 22:19, 11 May 2017 (UTC)
References
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Ideal sources for Wikipedia's health content are defined in the guideline
Wikipedia:Identifying reliable sources (medicine) and are typically
review articles. Here are links to possibly useful sources of information about Paclitaxel.
|
This article is rated C-class on Wikipedia's
content assessment scale. It is of interest to the following WikiProjects: | |||||||||||||||||||||
|
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)
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)
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.
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. 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
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)
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 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. -- DLuber1 17:37, 6 August 2007 (UTC) -DL
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)
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)
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?
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)
See this press release.
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)
Is this considered a chemo drug?
ACETYLOXY IS ETHANOILOXY ? —Preceding unsigned comment added by 89.77.15.69 ( talk) 02:42, 15 September 2007 (UTC)
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)
(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)
Please do not revert the edit to which this Talk section refers [2], 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:
"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 [4].)
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: [8]), 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)
…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 citation needed 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):
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 Leprof 7272 ( talk) 14:32, 2 June 2014 (UTC)
… 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)
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)
The announcement of intent to edit the lede vis-a-vis its ongoing POV issue, see [9], 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)
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)
Should we go with
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? Doc James ( talk · contribs · email) 22:30, 3 May 2017 (UTC)
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. • • • Peter (Southwood) (talk): 16:19, 5 May 2017 (UTC)
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)
01:17, 11 May 2017 (UTC)
Others thoughts on "use during pregnancy may cause birth defects"? Should we go with that? Doc James ( talk · contribs · email) 22:19, 11 May 2017 (UTC)
References
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