Tibolone

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[1]
Drug classProgestogen; Progestin; Estrogen; Androgen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability92%[5]
Protein binding96.3% (to albumin; low affinity for SHBGTooltip sex hormone-binding globulin)[5]
MetabolismLiver, intestines (hydroxyl-ation, isomerization, conjugation)[1][8]
Metabolites• Δ4-Tibolone[6]
• 3α-Hydroxytibolone[6]
• 3β-Hydroxytibolone[6]
• Sulfate conjugates[7]
Elimination half-life45 hours[8]
ExcretionKidney: 40%[5]
Feces: 60%[5]
Identifiers
IUPAC name
  • (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)
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
  (verify)

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.[1][9][10][11] The medication is available alone and is not formulated or used in combination with other medications.[12] It is taken by mouth.[1]

Side effects of tibolone include acne and increased hair growth among others.[8] Tibolone is a synthetic steroid with weak estrogenic, progestogenic, and androgenic activity, and hence is an agonist of the estrogen, progesterone, and androgen receptors.[13][1][8][6] It is a prodrug of several metabolites.[1][13][14] The estrogenic effects of tibolone may show tissue selectivity in their distribution.[13][15][14][16]

Tibolone was developed in the 1960s and was introduced for medical use in 1988.[17][18] It is marketed widely throughout the world.[12][19] The medication is not available in the United States.[12][19]

  1. ^ a b c d e f Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. ^ Cite error: The named reference CDSA1996 was invoked but never defined (see the help page).
  3. ^ "Summary Basis of Decision (SBD) for Tibella". Health Canada. 23 October 2014. Retrieved 29 May 2022.
  4. ^ "Livial 2.5mg tablets - Summary of Product Characteristics (SmPC)". (emc). 29 September 2020. Retrieved 8 November 2020.
  5. ^ a b c d Cite error: The named reference MHRA-PAR was invoked but never defined (see the help page).
  6. ^ a b c d Cite error: The named reference pmid19464167 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference pmid15145448 was invoked but never defined (see the help page).
  8. ^ a b c d Albertazzi P, Di Micco R, Zanardi E (November 1998). "Tibolone: a review". Maturitas. 30 (3): 295–305. doi:10.1016/S0378-5122(98)00059-0. PMID 9881330.
  9. ^ Ganellin CR, Triggle DJ (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1974–. ISBN 978-0-412-46630-4.
  10. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 275–. ISBN 978-94-011-4439-1.
  11. ^ "Tibolone". AdisInsight.
  12. ^ a b c Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  13. ^ a b c Cano A (2 November 2017). Menopause: A Comprehensive Approach. Springer. pp. 103–. ISBN 978-3-319-59318-0.
  14. ^ a b Falcone T, Hurd WW (14 June 2017). Clinical Reproductive Medicine and Surgery: A Practical Guide. Springer. pp. 182–. ISBN 978-3-319-52210-4.
  15. ^ Cite error: The named reference SchneiderNaftolin2004 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference KingBrucker2010 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference FritzSperoff2012 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference de VriesBromley2005 was invoked but never defined (see the help page).
  19. ^ a b Cite error: The named reference CouncilMedicine2003 was invoked but never defined (see the help page).
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