Paclitaxel chemical structure
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Taxol

Paclitaxel (Taxol®) is a drug used in the treatment of cancer. It was discovered at Research Triangle Institute (RTI) in 1967 when Dr. Monroe E. Wall and Dr. Mansukh C. Wani isolated the compound from the bark of the Pacific yew tree, Taxus brevifolia, and noted its antitumor activity in a broad range of rodent tumors. By 1970, the two scientists had determined the structure of paclitaxel, which is extremely complex. Paclitaxel has since become an effective tool of doctors who treat patients with lung, ovarian, breast cancer, and advanced forms of Kaposi's sarcoma (Saville et al 1995). It is sold under the tradename Taxol®. Together with docetaxel, it forms the drug category of the taxanes. more...

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Paclitaxel is also used for the prevention of restenosis (recurrent narrowing) of coronary stents; locally delivered to the wall of the coronary artery, a paclitaxel coating limits the growth of neointima (scar tissue) within stents (Heldman et al 2001).

History

The history of paclitaxel begins with a 1958 National Cancer Institute study that commissioned Department of Agriculture botanists to collect samples of over 30,000 plants to test for anticancer properties. Arthur S. Barclay, one of those botanists, collected 15 lbs of twigs, needles, and bark from Pacific yew trees in a forest near Mount St. Helens. Months later, in 1963, Monroe E. Wall discovered that bark extract from the Pacific yew possessed antitumor qualities, beginning to reveal the tree's hidden treasure. Soon after, Wall and his colleague Mansukh C. Wani were busy isolating and purifying plant compounds for anticancer tests in Research Triangle Park, North Carolina. In 1967 the team had isolated the active ingredient, announcing their findings at a American Chemical Society meeting in Miami Beach. Wall and Wani published their results, including the chemical structure, in a 1971 issue of the Journal of the American Chemical Society. The paper was noticed immediately by Robert A. Holton who was starting postdoctoral research at Stanford University in natural products synthesis. But, it would be several years before he dedicated his attention to synthesizing pacilitaxel at Florida State University, quelling an emerging environmental controversy; a 40-foot Pacific yew tree, which may have taken 200 years to reach that height, yields only a half gram of paclitaxel, but Holton's group perfected a four-step procedure to convert 10-deacetylbaccatin (a related compound in Pacific yew needles) into paclitaxel. In the late 1970s, Susan B. Horwitz, a molecular pharmacologist at Albert Einstein College of Medicine in New York City, unraveled the key mystery of how paclitaxel works. Largely in part of an enormous research and development effort, starting in government facilities and later in commercial labs, paclitaxel quickly became an all-time best-selling pharmaceutical. Paclitaxel was brought to the market by Bristol-Myers Squibb in 1993 as Taxol®. Annual sales peaked in 2000, reaching US$1.6 billion.

Production

Unfortunately, the Pacific yew is one of the slowest growing trees in the world. Further, the treatment of just one patient requires the cutting down and processing of six 100-year old trees. This supply problem combined with the threat to the endangered spotted owl (Strix occidentalis) has prompted researchers to develop actinobacteria such as Streptomyces coelicolor or Amycolata autotrophica from which paclitaxel-like epothilone compounds can be obtained by fermentation. S. coelicolor produces epothilone A and epothilone B, while A. autotrophica produces epothilone D. Similarly, cultures of the fungus Nodulisporium sylviforme can be used to produce paclitaxel itself.

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The Story of Taxol: Nature and Politics in the Pursuit of an Anti-Cancer Drug $9.11 Technology Transfer: NIH-Private Sector Partnership in the Development of Taxol. : An article from: General Accounting Office Reports & Testimony $5.95
Part I: Stucture and dynamics of beta-amyloid fibrils. Part II: Design of Taxol (Paclitaxel) analogs and predictive models; design of measles virus inhibitors; ... of alpha-helical mimics : (Dissertation) $55.00 Progress in the Chemistry of Organic Natural Products (Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products) $69.89
Taxane Anticancer Agents : Basic Science and Current Status (ACS Symposium Series) $17.65 Syntheses and bioactivities of targeted and conformationally restrained taxol analogs : (Dissertation) $55.00
Ovarian cancer vs. the spotted owl. (using taxol in Pacific yew trees as cancer treatment also poses threat to endangered species) : An article from: Medical Update $5.95 The Chemistry and Pharmacology of Taxol(R) and its Derivatives $61.99
TAXOL: Science and Applications $71.92 Biological physics studies of microtubules, taxol, and the microtubules-associated protein, tau : (Dissertation) $55.00

Taxol update
In the Sept./Oct. 1991 issue of The Saturday Evening Post, you featured a rather extraordinary article about Taxol, an anticancer drug. Bristol-Myers ...
Radial Compression of Microtubules and the Mechanism of Action of Taxol and Associated Proteins
ABSTRACT Microtubules (MTs) are hollow cylindrical polymers composed of αβ-tubulin heterodimers that align head-to-tail in the MT wall, forming linear ...
Portion of plant enzyme may mimic taxol
Researchers interested in increasing plant cells' use of carbon for seed storage products like starch, oil, and protein have been studying sucrose synthase.
Gemzar/Taxol combo approved
Gemzar (gemcitabine HCl), in combination with Taxol (paclitaxel) is approved for the first-line treatment of metastatic breast cancer after failure of ...
Nutty and fungi-ble taxol sources - hazelnut trees are new source of paclitaxel - Brief Article
Scouting for chemical clues to the puzzle of why eastern filbert blight hits some hazelnut cultivars harder than others, Angela M. Hoffman and her colleagues ...
Mobility of taxol in microtubule bundles
ABSTRACT Mobility of taxol inside microtubules was investigated using fluorescence recovery after photobleaching on flow-aligned bundles. Bundles were ...
Court questions generic Taxol marketing - Generics Watch - FDA questions Ivax's right to market drug - Brief Article
The generic version of the breast cancer drug Taxol (paclitaxel) could be pulled off the market if a recent federal court ruling stands. A Nov. 6 federal ...
Mylan wins rights to generic Taxol injection - Mylan Laboratories - Brief Article
Mylan Laboratories received Food and Drug Administration approval on July 23 to market an injection form of paclitaxel, the generic form of major oncology ...

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