Cyproterone

Structural formula
General
Non-proprietary name	Cyproterone
other names	6-chloro-Δ 6 -1.2 α -methylene-17 α -hydroxyprogesterone 6-chloro-17-hydroxy-1 α , 2 α -cyclopropa [1,2] pregna-4,6-diene-3,20-dione
Molecular formula	C 22 H 27 ClO 3
External identifiers / databases
CAS number 2098-66-0 (cyproterone) 427-51-0 (acetate) EC number 690-915-7 ECHA InfoCard 100.218.313 PubChem 5284537 ChemSpider 4447594 DrugBank DB04839 Wikidata Q7381206
Drug information
ATC code	G03 HA01
Drug class	Antiandrogens , progestins
Mechanism of action	competitive androgen receptor - antagonist
properties
Molar mass	374.91 g mol −1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances acetate Caution H and P phrases H: 312 + 332-351 P: 261-280
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyproterone is a synthetic progesterone - derivative . It acts as a competitive antagonist on the androgen receptor , has a gestagenic and an antiandrogenic component. The antiandrogenic effect is mediated by a cis -linked cyclopropane ring in ring A of the steroid skeleton.

The acetic acid ester of cyproterone, cyproterone acetate, is usually used. The use of the preparation is limited, as the active ingredient is dose-dependently associated with the occurrence of meningiomas .

effect

The active ingredient is used therapeutically for hypersexuality , severe forms of acne , hirsutism (increased hairiness) and female alopecia ( androgen-related hair loss).

In transsexual women it is used in combination with estrogens to support feminization . As a rule, far less than 50 mg per day (about 5 to 10 mg) is sufficient to achieve the desired feminizing effects, such as a reduction in body hair , body odor and muscles , slowing down to stopping alopecia (androgenetic hair loss) and breast growth . In trans women who have not undergone sex reassignment surgery , cyproterone suppresses spermiogenesis , as in men .

For metastatic and inoperable prostate cancer , cyproterone is an alternative to treatment with GnRH analogues . Another indication is hormonal castration .

Side effects

In men, the most commonly reported side effects are decreased sex drive ( libido ), erectile dysfunction and reversible inhibition of spermatogenesis , in women , intermenstrual bleeding , weight gain and depressive moods. Changes in the mammary gland ( gynecomastia ) and tiredness are common in men, the frequency is not known in women (chest pain and tightness, tiredness). In both sexes, the most serious side effects are benign and malignant liver tumors and thromboembolic events , but these occur very rarely.

Women who take cyproterone acetate in combination with ethinylestradiol are at an increased risk of thromboembolism such as pulmonary embolism , venous thrombosis , stroke or heart attack . After deaths occurred in France, the French drug authorities demanded the withdrawal of the fixed combination of 2 mg cyproterone acetate and 35 µg ethinylestradiol in France; The European Medicines Agency then initiated a risk assessment process for such preparations in February 2013.

In June 2013, the manufacturers and distributors of preparations with the active ingredient combination cyproterone acetate / ethinylestradiol informed in Rote-Hand-Letters about this benefit-risk assessment by the EMA together with a warning about an increased risk of venous and arterial thromboembolism (VTE and ATE) .

In February 2020, the Pharmacovigilance Risk Assessment Committee (PRAC) of the European Medicines Agency (EMA) recommended additional safety measures when prescribing cyproterone. This is to minimize the risk of meningiomas , i.e. benign brain tumors. It is advised to use cyproterone in doses of 10 mg or more daily only for hirsutism , alopecia , acne and seborrhea , if other treatment options, including therapy with lower amounts of the drug, have failed. As soon as higher doses begin to work, the dose should be reduced again. The recommendations are even more extensive and can be read in the original of the report.

Drug tests

The journalist Charly Kowalczyk reports in a feature on Deutschlandfunk about drug tests of the preparation Androcur on men with intellectual disabilities. On SWR2 he tries to find out possible long-term consequences of the experimental administration of cyproterone acetate to adolescents in a German home at the beginning of the 1970s on the basis of an individual fate.

Trade names

Monopreparations

Androbas (CH), Androcur (D, A, CH), Andro-Diane (A), MaskuPel (A), Virilit (D), Generika (D, CH), Cyprostat (AU)

Combination preparations

Attempta (D), Bella HEXAL (D), Bellgyn (A), Clevia (D), Climen (D, A, CH), Cyproderm (D), Cypestra (CH), Dialuna (A), Diane (D, A , CH), Elleacnelle (CH), Ergalea (D), Feminac (CH), Femogyn (A), Holgyeme (CH), Midane (A), Minerva (A, CH), Morea Sanol (D), Xylia (A ), Generics (A)

Individual evidence

1. ↑ ^{a b} data sheet Cyproterone acetate from Sigma-Aldrich , accessed on June 30, 2019 ( PDF ).
2. ↑ External identifiers or database links for cyproterone acetate : CAS number: 427-51-0, EC number: 207-048-3, ECHA InfoCard: 100.006.409 , PubChem : 9880 , ChemSpider : 9496 , DrugBank : DB04839 , Wikidata : Q426185 .
3. ^ Weill A., ea: Exposition prolongée à de fortes doses d'acétate de cyprotérone et risque de méningiome chez la femme ; Revue d'Épidémiologie et de Santé Publique, Volume 68, Supplement 1, March 2020, pages S3-S4, pdf ; last viewed on April 29, 2020
4. ↑ Product information Androcur 50 mg tablets, as of June 2011.
5. ↑ European Medicines Agency starts safety review of Diane 35 and its generics , press release of the European Medicines Agency (EMA) of February 8, 2013.
6. ↑ Rote Hand Brief June 2013 (PDF; 291 kB) Retrieved on February 23, 2016 . 
7. ↑ Meeting highlights from the Pharmacovigilance Risk Assessment Committee (PRAC) February 10-13, 2020 , PM EMA February 14, 2020, accessed on February 17, 2020
8. ↑ Charly Kowalczyk: Mentally disabled people as guinea pigs pdf , December 13, 2016.
9. ↑ https://www.sueddeutsche.de/gesundheit/deutschland-kork-triebhemmer-medikamente-schering-1.4388763
10. ↑ Looking for Schorsch. Drug trials on adolescents and their consequences , SWR2, five-part feature series by Charly Kowalczyk (each episode about 27:00 min), September 19, 2018. Retrieved October 23, 2018
11. ↑ In the footsteps of Schorsch. Drug trials on adolescents and their consequences , SWR2, audio feature by Charly Kowalczyk (53:46 min), September 18, 2018. Accessed October 23, 2018

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !