Taxanes

Author: Prof. Dr. med. Peter Altmeyer

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Last updated on: 19.01.2021

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Synonym(s)

Deterpenoids; Diterpenes; Taxus brevifolia

Definition
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Taxanes are naturally occurring mitosis-inhibiting cytostatic drugs, i.e. substances that inhibit cell division. Chemically, taxanes belong to the diterpenoids (diterpenes). The substance group has been used in oncological therapy since the end of the 1990s.

Taxanes could be extracted in the 60ies of the last century in the USA from samples of the bark of the Pacific yew (Taxus brevifolia). Such bark extracts were effective against several leukemia cell lines in mice. The active ingredient in the yew extracts was later isolated and defined as paclitaxel. At the end of 1990, a technical route for the mass production of the cytostatic drug could be found. In 1993, paclitaxel (trade name Taxol®) was approved in Germany for the treatment of ovarian cancer.

Later, it was possible to synthesize docetaxel, a derivative of paclitaxel (it also largely exhibits its properties), from the needles of the European yew tree (Taxus baccata). Docetaxel acts at a lower dose than paclitaxel and is indicated for breast carcinoma, non-small cell lung carcinoma, gastric carcinoma, head and neck carcinoma and prostate carcinoma.

Another taxane is cabazitaxel, a docetaxel derivative. It is used in second-line therapy for hormone-refractory metastatic prostate cancer.

Pharmacodynamics (Effect)
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Taxanes inhibit cell division by interfering with the depolymerization and thus the degradation of the microtubules of cells. This inhibits the physiological dissolution of the microtubular cytoskeleton and thus the degradation of the mitotic spindles. This leads to cell death in the G2 phase or M phase of cell division.

Undesirable effects
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Taxanes cause a number of dermatological side effects: multiforme exanthema, hand-foot syndrome, hair loss, folliculitis.

Note(s)
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The tubular microtubules form the spindle apparatus of the cells.

Literature
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  1. Marks DH et al (2018) Evaluation of Prevention Interventions for Taxane-Induced Dermatologic Adverse Events: A Systematic Review. JAMA Dermatol 154:1465-1472.
  2. Picard M (2017) Management of Hypersensitivity Reactions to Taxanes. Immunol Allergy Clin North Am 37:679-693.
  3. Sibaud V et al (2016) Dermatological adverse events with taxane chemotherapy. Eur J Dermatol 26:427-443.

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Last updated on: 19.01.2021