Talk:Paclitaxel

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    [edit] 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. Js229 11:26, 10 September 2007 (UTC)

    [edit] 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. 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


    [edit] 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 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 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? 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 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


    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 --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 :) Js229 21:59, 7 August 2007 (UTC)

    [edit] 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.

    lots of issues | leave me a message 08:30, 24 May 2005 (UTC)

    {{Sofixit}}. Also, your signature is confusing! JFW | T@lk 12:51, 24 May 2005 (UTC)


    [edit] License and name

    I have put hte 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)

    [edit] 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.

    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).

    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)e_heider

    [edit] Updates

    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)

    [edit] Pierre Poter

    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)

    [edit] 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. Dr. Cash 02:43, 29 September 2007 (UTC)

    [edit] IUPAC

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

    [edit] 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)- —Preceding unsigned comment added by 24.162.249.146 (talk) 01:55, 28 September 2007 (UTC)

    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)
    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)