Exemestane
Structural formula | |||||||||||||||||||
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Non-proprietary name | Exemestane | ||||||||||||||||||
other names |
6-methylideneandsta-1,4-diene-3,17-dione ( IUPAC ) |
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Molecular formula | C 20 H 24 O 2 | ||||||||||||||||||
Brief description |
colorless solid |
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properties | |||||||||||||||||||
Molar mass | 296.40 g mol −1 | ||||||||||||||||||
solubility |
soluble in DMSO |
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safety instructions | |||||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Exemestane is a drug from the group of aromatase inhibitors . After anastrozole and letrozole, it is the third orally effective selective aromatase inhibitor for the treatment of advanced breast cancer .
Mechanism of action
Exemestane inhibits estrogen production by irreversibly blocking the conversion of androgens to estrone and estradiol in non- ovarian tissues. The structure of exemestane is similar to that of the natural substrate androstenedione . Exemestane lowers the estrogen level to 5 to 10% of the initial value and has a half-life of two days. A daily dose of 25 mg causes a reduction of the total aromatase activity by up to 98%. Exemestane has no gestagenic or estrogenic effects.
application areas
Exemestane is indicated for the supportive treatment of hormone-dependent ( estrogen receptor- positive) breast cancer after the menopause, if previous treatment with the antiestrogen tamoxifen has not worked.
Abuse as a doping agent
Exemestane increases the luteinizing hormone (LH) and the follicle-stimulating hormone (FSH) independently of the dose and thus creates a rapid dominance of the male sex hormones, which increases performance.
It is also used to prevent excessive aromatase production after testosterone administration . Excessive aromatase production leads to gynecomastia and increased water and fat storage.
The active ingredient was placed on the prohibited list by the World Anti-Doping Agency (WADA) in 2008 . Possession of more than 750 mg is classified as a "not small amount" according to the German Medicines Act , according to the doping agent quantity regulation .
Side effects
The most common side effects that may occur with exemestane therapy include
- very common side effects (affects more than 1 in 10 people)
- Hot flashes and rednesses (flushes)
- fatigue
- a headache
- nausea
- depressions
- sleep disorders
- Muscle and joint pain
- common side effects (affects 1 to 10 users in 100)
- Loss of appetite
- depressions
- dizziness
- Carpal tunnel syndrome (combination of numbness, pins and needles, and pain in the whole hand except the little finger)
- stomach pain
- Rash, hair loss
A 2011 study also reported a deterioration in blood lipid levels.
Trade names
Aromasin ( D , A , CH and others), various generics
Individual evidence
- ↑ a b c d Data sheet Exemestane, ≥ 98% (HPLC) from Sigma-Aldrich , accessed on December 23, 2011 ( PDF ).
- ↑ Scientific evaluation of the Institute for Clinical Pharmacology, Klinikum Bremen Mitte gGmbH, (PDF; 626 kB).
- ↑ COOMBES, RC: Recent Results Cancer Res. 1998; 152: 277-284.
- ↑ a b Technical information Aromasin , as of May 2009.
- ↑ The Black Book - Anabolic Steroids. 2007, p. 133, ISBN 978-3-00-020944-4 .
- ↑ Substance Classification Booklet ( Memento of the original from September 27, 2013 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF file; 687 kB), Canadian Center for Ethics in Sport, Version 4.0, January 2009.
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↑ Cornelis JH van de Velde et al .: Adjuvant tamoxifen and exemestane in early breast cancer (TEAM): a randomized phase 3 trial. In: The Lancet. Volume 377, No. 9762, 2011, pp. 321-331, doi: 10.1016 / S0140-6736 (10) 62312-4
Adjuvant breast cancer therapies with the same event-free survival rates but different side effects. On: Wissenschaft-online.de from January 21, 2011.