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Paclitaxel, commonly known by its trade name Taxol, is a chemotherapy drug that has been used to treat many types of cancer. Despite its several adverse side effects, it is on the World Health Organization's List of Essential Medicines.
In 1971, as the sixth part of a series of articles on plant antitumor agents, Mansukh C. Wani and colleagues at the Research Triangle Institute (NC) and Duke University (Durham, NC) reported the isolation of a (Taxus brevifolia) that they named 鈥渢axol鈥�. In the article鈥檚 introduction, the authors state, 鈥淭axol has potent antileukemic and tumor inhibitory properties and is the first compound possessing the taxane ring [that] has been demonstrated to have such activity.鈥� The taxane 鈥渞ing鈥� is actually a tricyclic structure that forms the core of the molecule (see images).
Wani et al. provided very little information about 鈥渢axol鈥檚鈥� anticancer activity; the article focused on the chemistry and spectra of the compound and some of its derivatives. During the next two decades, Wani, his colleague Monroe E. Wall, and several other researchers, under the auspices of the National Cancer Institute (NCI), investigated the potential drug鈥檚 activity against various cancers. They began clinical trials in 1984. During the 1970s and 鈥�80s, almost 10 t of Pacific yew bark were harvested and extracted for experimental work and the trials.
Finally, in 1989, NCI offered to turn the project over to a commercial pharmaceutical company. The offer generated surprisingly little interest; but by the end of the year, the technology was transferred to Bristol-Meyers Squibb (BMS)鈥攖he same year that the BMS merger was concluded. BMS obtained the generic name paclitaxel for the drug and registered the brand name Taxol with the US Office of Patents and Trademarks. The NCI鈥揃MS deal and the trademarked name soon became the subject of much .
BMS received its first drug approval for paclitaxel from the US Food and Drug Administration in 1992. As of 2018, FDA approvals include treatment of breast, pancreatic, ovarian, and non鈥搒mall-cell lung cancers; and Kaposi's sarcoma. Paclitaxel has been extremely thoroughly researched: As of this writing, SciFinder lists 73,164 references, including mentions in 68 United States and international patents.
Paclitaxel hazard information*
Hazard class** | Hazard statement | |
---|---|---|
Acute toxicity, oral, category 4 | H302鈥擧armful if swallowed | ![]() |
Acute toxicity, dermal, category 4 | H312鈥擧armful in contact with skin | ![]() |
Skin corrosion/irritation, category 2 | H315鈥擟auses skin irritation | ![]() |
Skin sensitization, category 1 | H317鈥擬ay cause an allergic skin reaction | ![]() |
Serious eye damage/eye irritation, category 1 | H318鈥擟auses serious eye damage聽 | ![]() |
Acute toxicity, inhalation, category 4 | H332鈥擧armful if inhaled | ![]() |
Respiratory sensitization, category 1 | H334鈥擬ay cause allergy or asthma symptoms or breathing | ![]() |
Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335鈥擬ay cause respiratory irritation | ![]() |
Germ cell mutagenicity, category 2 | H341鈥擲uspected of causing genetic defects | ![]() |
Reproductive toxicity, category 1B | H360鈥擬ay damage fertility or the unborn child | ![]() |
Hazardous to the aquatic environment, long-term hazard, category 4聽 | H413鈥擬ay cause long-lasting harmful effects to aquatic life |
聽*Globally Harmonized System of Classification and Labeling of Chemicals.
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Paclitaxel fast facts
CAS Reg. No. | 33069-62-4 |
nomenclature | See SciFinder listing |
Empirical formula | C47H51NO14 |
Molar mass | 853.91 g/mol |
Appearance | White crystalline powder |
Melting point | 213鈥�216 潞C |
Water solubility聽 | 鈮�10鈥�20 mg/L (est.) |
MOTW update
N-Nitrosodimethylamine (NDMA) was the Molecule of the Week for January 14, 2019. It is used to make rocket fuel; but, because it is extremely toxic, it is notorious for its use in some fatal poisonings. NDMA and other nitrosamines have been found as impurities in several prescription drugs. Earlier this month, the US Food and Drug Administration issued guidelines on acceptable limits of six nitrosamine impurities. The .

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