Tibolone

Structural formula
General
Surname	Tibolone
other names	17-Hydroxy-7 α -methyl-19-nor-17 α -pregn-5 (10) -en-20-yn-3-one; (7 α , 17 β ) -17-ethynyl-17-hydroxy-7-methylestr-5 (10) en-3-one;
Molecular formula	C 21 H 28 O 2
External identifiers / databases
EC number	227-069-1
ECHA InfoCard	100.024.609
PubChem	444008
ChemSpider	392038
DrugBank	DB09070
Wikidata	Q413805
Drug information
ATC code	G03 CX01
properties
Molar mass	312.45 g · mol -1
Physical state	firmly
Melting point	165-169 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 319
	P: 305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tibolone is a synthetically produced drug with hormone effects that is used for hormone replacement therapy in postmenopausal women . It is a tissue-selective effective regulator of the estrogenic activity ( English selective tissue estrogenic activity regulator , STEAR ).

Chemically speaking, tibolone is a steroid that is structurally similar to norethisterone and has estrogenic , gestagenic and androgenic effects. After oral administration, tibolone is rapidly metabolized, whereby three active metabolites are formed, which contribute significantly to the effect: the Δ ⁴ isomer has predominantly gestagenic and androgenic effects, the two substances hydroxylated in position 3 3α-OH-tibolone and 3β- OH-tibolone, on the other hand, has an estrogen-like effect. Tibolone is used to treat menopausal symptoms in postmenopause.

In some countries, e.g. B. in Switzerland, tibolone is also approved for the prevention of postmenopausal osteoporosis . In most tissues, 3α- and 3β-hydroxytibolone are converted into inactive , sulfated metabolites by the sulfotransferases that occur there . On the other hand, since there are not only fewer sulfotransferases but also more sulphatases , which hydrolytically convert the conjugates back into the active metabolites, in bone tissue in particular, bone breakdown should be inhibited in this way.

The adverse effects include an increased risk of stroke or breast cancer .

Trade names

Liviella ( D ( Essex Pharma )), Heria ( B ), Livial ( CH (Essex Pharma); e.g. A , NL , DK , N , S , F etc. ( Organon ))

Individual evidence

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 1620, ISBN 978-0-911910-00-1 .
↑ ^a ^b Tibolone data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).

↑ EP1563833B1: Pharmaceutical preparations with amorphous tibolone .

^ Deutsches Ärzteblatt: Tibolone: Risks similar to estrogens (May 13, 2005).

↑ ^a ^b Mutschler, Ernst: Mutschler drug effects. Pharmacology, clinical pharmacology, toxicology. 10th edition. Stuttgart. 2013; P. 418.

↑ B. Fuchs et al .: Tibolon - A synthetic steroid against menopausal complaints , Pharmazeutische Zeitung Ausg. 47, 2002.

↑ USA - no approval of tibolone (LIVIELLA) for menopausal symptoms ( Memento from January 1, 2017 in the Internet Archive ) , arznei-telegram 2006; 37:67.

[MERCK_Index-1] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 1620, ISBN 978-0-911910-00-1 .

[Sigma-2] Tibolone data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).

[3] EP1563833B1: Pharmaceutical preparations with amorphous tibolone .

[4] Deutsches Ärzteblatt: Tibolone: Risks similar to estrogens (May 13, 2005).

[mutsch-5] Mutschler, Ernst: Mutschler drug effects. Pharmacology, clinical pharmacology, toxicology. 10th edition. Stuttgart. 2013; P. 418.

[6] B. Fuchs et al .: Tibolon - A synthetic steroid against menopausal complaints , Pharmazeutische Zeitung Ausg. 47, 2002.

[7] USA - no approval of tibolone (LIVIELLA) for menopausal symptoms ( Memento from January 1, 2017 in the Internet Archive ) , arznei-telegram 2006; 37:67.