Taxol

What is taxol?

Taxol or paclitaxel (PTX) is a drug used in chemotherapy for the treatment of various types of cancer (ovarian, breast and lung). The mechanism of action of taxol is based on its ability to stabilize microtubules, which are structural components of the cell’s cytoskeleton. By stabilizing microtubules, taxol prevents their normal disassembly, leading to cell cycle arrest and apoptosis (programmed cell death) of cancer cells. Taxol has also been studied for its potential in the treatment of other diseases, including autoimmune disorders and neurodegenerative diseases.

It was first isolated in 1971 from bark of the Pacific yew tree, a conifer (Taxus brevifolia), and in 1993 its first use in medicine was approved.

Its molecular formula is (C47H51NO14), and its IUPAC systematic name is (2α,4α,5β,7β,10β,13α)-4,10-Bis(acetyloxy)-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate.

Taxol is a highly stable molecule and is not easily degraded by light, heat, or acidic conditions.

Structure

Taxol is a complex molecule, highly branched one that contains a taxane nucleus, which gives it its unique chemical properties. The main structural feature of taxol is that it has a 17-membered tetracyclic skeleton, with a total of 11 stereocenters. The active stereoisomer is (-)-taxol.

taxol RCINICONZNJXQF-MZXODVADSA-N paclitaxel PTX
Taxol RCINICONZNJXQF-MZXODVADSA-N
3D Structure

 

GHS classification

Pictogram: Corrosive, irritant, health hazards.ghsghsghs

  • Health hazard H-phrases: H315, H318, H317, H361, H335
  • Environmental hazard H-phrase: H413
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