Exemestane

Structural formula
General
Non-proprietary name	Exemestane
other names	6-methylideneandsta-1,4-diene-3,17-dione ( IUPAC )
Molecular formula	C 20 H 24 O 2
Brief description	colorless solid
External identifiers / databases
EC number	643-090-2
ECHA InfoCard	100.171.149
PubChem	60198
DrugBank	DB00990
Wikidata	Q418819
Drug information
ATC code	L02 BG06
Mechanism of action	Aromatase inhibitors
properties
Molar mass	296.40 g mol −1
solubility	soluble in DMSO
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 319-360
	P: 201-305 + 351 + 338-308 + 313
	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. @1@ 2

↑ 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.

[Sigma-1] Data sheet Exemestane, ≥ 98% (HPLC) from Sigma-Aldrich , accessed on December 23, 2011 ( PDF ).

[2] Scientific evaluation of the Institute for Clinical Pharmacology, Klinikum Bremen Mitte gGmbH, (PDF; 626 kB).

[3] COOMBES, RC: Recent Results Cancer Res. 1998; 152: 277-284.

[FI-4] Technical information Aromasin , as of May 2009.

[5] The Black Book - Anabolic Steroids. 2007, p. 133, ISBN 978-3-00-020944-4 .

[6] 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. @1@ 2

[7] 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.