Tibolone

Tibolone, sold under the brand name Livial among others, is a medication which is used in menopausal hormone therapy and in the treatment of postmenopausal osteoporosis and endometriosis. The medication is available alone and is not formulated or used in combination with other medications. It is taken by mouth.

Tibolone
Clinical data
Trade namesLivial, Tibella, Tibofem, others
Other namesTIB; ORG-OD-14; 7α-Methylnoretynodrel; 7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone; 17α-Ethynyl-7α-methylestr-5(10)-en-17β-ol-3-one; 7α-Methyl-19-nor-17α-pregn-5(10)-en-20-yn-17-ol-3-one
AHFS/Drugs.comProfessional Drug Facts
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
Drug classProgestogen; Progestin; Estrogen; Androgen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability92%
Protein binding96.3% (to albumin; low affinity for SHBGTooltip sex hormone-binding globulin)
MetabolismLiver, intestines (hydroxyl-ation, isomerization, conjugation)
Metabolites• Δ4-Tibolone
• 3α-Hydroxytibolone
• 3β-Hydroxytibolone
• Sulfate conjugates
Elimination half-life45 hours
ExcretionUrine: 40%
Feces: 60%
Identifiers
  • (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.024.609
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
  • 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=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
  (verify)

Side effects of tibolone include acne and increased hair growth among others. Tibolone is a synthetic steroid with weak estrogenic, progestogenic, and androgenic activity, and hence is an agonist of the estrogen, progesterone, and androgen receptors. It is a prodrug of several metabolites. The estrogenic effects of tibolone may show tissue selectivity in their distribution.

Tibolone was developed in the 1960s and was introduced for medical use in 1988. It is marketed widely throughout the world. The medication is not available in the United States.

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