Tibolone

Tibolone
Clinical data

AHFS/Drugs.com	International Drug Names
Pregnancy category	ADEC Category D
Routes of administration	oral
ATC code	G03CX01 (WHO)
Legal status
Legal status	CA: Schedule IV
Identifiers
IUPAC name 17-Hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3-one
Synonyms	7α-Methylnoretynodrel; Org OD 14 (7α,17β)-17-ethynyl-17-hydroxy-7-methylestr-5(10)-en-3-one
CAS Number	5630-53-5^N
PubChem CID	444008
ChemSpider	392038^Y
UNII	FF9X0205V2
KEGG	D01639^Y
ChEBI	CHEBI:32223^Y
ChEMBL	CHEMBL1558898^N
ECHA InfoCard	100.024.609
Chemical and physical data
Formula	C₂₁H₂₈O₂
Molar mass	312.446 g/mol
3D model (Jmol)	Interactive image
SMILES O=C4CCC\1=C(\C[C@H]([C@@H]2[C@@H]/1CC[C@]3([C@H]2CC[C@]3(C#C)O)C)C)C4
InChI InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3/t13-,17-,18+,19-,20+,21+/m1/s1^Y Key:WZDGZWOAQTVYBX-XOINTXKNSA-N^Y
^NY (what is this?)

Tibolone (INN, USAN, BAN) (brand name Livial, Tibofem), also known as 7α-methylnoretynodrel, is a synthetic steroid drug with estrogenic, progestogenic, and weak androgenic actions which was introduced in 1988 and is used widely in Europe, Asia, Australasia, and, with the exception of the United States (where it is not available), the rest of the world. It is used mainly for treatment of endometriosis, as well as hormone replacement therapy in post-menopausal women. Tibolone has similar or greater efficacy compared to older hormone replacement drugs, but shares a similar side effect profile. It has also been investigated as a possible treatment for female sexual dysfunction.

Tibolone is a 19-nortestosterone derivative and is related structurally to other 19-nortestosterone progestins. It is the 7α-methyl derivative of noretynodrel.

Tibolone possesses a complex pharmacology. Its two major active metabolites, 3α-hydroxytibolone and 3β-hydroxytibolone, act as potent, fully activating agonists of the estrogen receptor (ER), with a high preference for ERα. Tibolone and its metabolite Δ⁴-tibolone act as agonists of the progesterone and androgen receptors, while 3α-hydroxytibolone and 3β-hydroxytibolone, conversely, act as antagonists of these receptors. Lastly, tibolone, 3α-hydroxytibolone, and 3β-hydroxytibolone act as antagonists of the glucocorticoid and mineralocorticoid receptors, with preference for the mineralocorticoid receptor.

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