From Wikipedia, the free encyclopedia
Clinical data
Trade names Livial, Tibofem
Synonyms 7α-Methylnoretynodrel; Org OD 14; 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.com International Drug Names
  • ADEC Category D
Routes of
By mouth
Drug class Progestin; Progestogen; Estrogen; Androgen; Anabolic steroid
ATC code
Legal status
Legal status
CAS Number
  • 5630-53-5 N
PubChem CID
  • 444008
  • 392038 YesY
  • FF9X0205V2
  • D01639 YesY
  • CHEBI:32223 YesY
  • CHEMBL1558898 N
ECHA InfoCard 100.024.609
Chemical and physical data
Formula C21H28O2
Molar mass 312.446 g/mol
3D model (JSmol)
  • Interactive image
 NYesY (what is this?)  (verify)

Tibolone, sold under the brand names Livial and Tibofem among others, is a synthetic steroid which is used in the treatment of endometriosis and for menopausal hormone therapy.[1][2][3] The drug was introduced in 1988 and is used widely in Europe, Asia, Australasia, and elsewhere in the world (but notably not in the United States).[4][5] Tibolone has progestogenic and estrogenic activity as well as weak androgenic activity.[1]

Medical uses

Tibolone is used in the treatment of endometriosis and menopausal symptoms.[1][6] It has similar or greater efficacy compared to older menopausal hormone therapy drugs, but shares a similar side effect profile.[7][8][9] It has also been investigated as a possible treatment for female sexual dysfunction.[10]

Side effects

A report in September 2009 from Health and Human Services' Agency for Healthcare Research and Quality suggests that tamoxifen, raloxifene, and tibolone used to treat breast cancer significantly reduce invasive breast cancer in midlife and older women, but also increase the risk of adverse side effects.[11]



Tibolone possesses a complex pharmacology.[12] 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.[12][13][14] Tibolone and its metabolite Δ4-tibolone act as agonists of the progesterone and androgen receptors,[13] while 3α-hydroxytibolone and 3β-hydroxytibolone, conversely, act as antagonists of these receptors.[12] Lastly, tibolone, 3α-hydroxytibolone, and 3β-hydroxytibolone act as antagonists of the glucocorticoid and mineralocorticoid receptors, with preference for the mineralocorticoid receptor.[12]

Tibolone has tissue-selective estrogenic effects, with desirable effects in bone, the brain, and the vagina, and lack of undesirable action in the endometrium and breasts.[14] Its tissue selectivity is the result of metabolism, enzyme modulation (e.g., of estrogen sulfatase and estrogen sulfotransferase), and receptor modulation that vary in different target tissues, and differs mechanistically from that of selective estrogen receptor modulators (SERMs) such as tamoxifen, which produce their tissue selectivity via means of modulation of the ER.[13][14] As such, to distinguish it from SERMs, tibolone has been described as a "selective tissue estrogenic activity regulator" (STEAR),[14] and also as a "selective estrogen enzyme modulator" (SEEM).[15]


Tibolone is a synthetic estrane steroid and is also known chemically as 7α-methyl-17α-ethynyl-19-nor-δ5(10)-testosterone or as 7α-methyl-17α-ethynyl-17β-hydroxy-19-norandrost-5(10)-en-3-one, as well as 7α-methylnoretynodrel.[1] It is a 19-nortestosterone derivative and is related structurally to other progestins of the 19-nortestosterone group.[16][17][18] It is the 7α-methyl derivative of noretynodrel.[1]


Tibolone was developed in the 1960s.[18] It was first introduced in the Netherlands in 1988, and was subsequently introduced in the United Kingdom in 1991.[19][20]

Society and culture

Generic names

Tibolone is the generic name of the drug and its INN, USAN, and BAN.[2][3]


  1. ^ a b c d e Kuhl, H (2009). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (sup1): 3–63. doi:10.1080/13697130500148875. ISSN 1369-7137. PMID 16112947. 
  2. ^ a b C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1974–. ISBN 978-0-412-46630-4. 
  3. ^ a b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 275–. ISBN 978-94-011-4439-1. 
  4. ^ Sheldon J. Segal Population Council; Division of Human Reproduction Luigi Mastroianni Jr. Professor, Department of Obstetrics and Gynecology University of Pennsylvania School of Medicine (4 October 2003). Hormone Use in Menopause and Male Andropause : A Choice for Women and Men: A Choice for Women and Men. Oxford University Press, USA. pp. 73–. ISBN 978-0-19-803620-3. 
  5. ^ Irwin Goldstein; Cindy M. Meston; Susan Davis; Abdulmaged Traish (17 November 2005). Women's Sexual Function and Dysfunction: Study, Diagnosis and Treatment. CRC Press. pp. 556–. ISBN 978-1-84214-263-9. 
  6. ^ Al Kadri H, Hassan S, Al-Fozan HM, Hajeer A (2009). Al Kadri, Hanan, ed. "Hormone therapy for endometriosis and surgical menopause". Cochrane Database of Systematic Reviews (1): CD005997. doi:10.1002/14651858.CD005997.pub2. PMID 19160262. 
  7. ^ Lazovic G, Radivojevic U, Marinkovic J (April 2008). "Tibolone: the way to beat many a postmenopausal ailments". Expert Opinion on Pharmacotherapy. 9 (6): 1039–47. doi:10.1517/14656566.9.6.1039. PMID 18377345. 
  8. ^ Garefalakis M, Hickey M (2008). "Role of androgens, progestins and tibolone in the treatment of menopausal symptoms: a review of the clinical evidence". Clinical Interventions in Aging. 3 (1): 1–8. PMC 2544356Freely accessible. PMID 18488873. 
  9. ^ Vavilis D, Zafrakas M, Goulis DG, Pantazis K, Agorastos T, Bontis JN (2009). "Hormone therapy for postmenopausal breast cancer survivors: a survey among obstetrician-gynaecologists". European Journal of Gynaecological Oncology. 30 (1): 82–4. PMID 19317264. 
  10. ^ Ziaei, S; Moghasemi, M; Faghihzadeh, S (2010). "Comparative effects of conventional hormone replacement therapy and tibolone on climacteric symptoms and sexual dysfunction in postmenopausal women". Climacteric : the journal of the International Menopause Society. 13 (2): 147–56. doi:10.1080/13697130903009195. PMID 19731119. 
  11. ^ "Medications Effective in Reducing Risk of Breast Cancer But Increase Risk of Adverse Effects, New Report Says". U.S. Department of Health & Human Services - Agency for Healthcare Research and Quality. September 2009. Retrieved 2 June 2014. 
  12. ^ a b c d Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, Balaguer P, Maudelonde T (August 2009). "Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites". The Journal of Steroid Biochemistry and Molecular Biology. 116 (1–2): 8–14. doi:10.1016/j.jsbmb.2009.03.008. PMID 19464167. 
  13. ^ a b c Tommaso Falcone; William W. Hurd (22 May 2013). Clinical Reproductive Medicine and Surgery: A Practical Guide. Springer Science & Business Media. pp. 152–. ISBN 978-1-4614-6837-0. 
  14. ^ a b c d Hermann P.G. Schneider; Frederick Naftolin (22 September 2004). Climacteric Medicine - Where Do We Go?: Proceedings of the 4th Workshop of the International Menopause Society. CRC Press. pp. 126–. ISBN 978-0-203-02496-6. 
  15. ^ Tekoa King; Mary C. Brucker (25 October 2010). Pharmacology for Women's Health. Jones & Bartlett Learning. pp. 371–. ISBN 978-0-7637-5329-0. 
  16. ^ Jorge R. Pasqualini (17 July 2002). Breast Cancer: Prognosis, Treatment, and Prevention. CRC Press. pp. 222–. ISBN 978-0-203-90924-9. 
  17. ^ Andrew P. Yao (2005). Trends in Breast Cancer Research. Nova Publishers. pp. 58–. ISBN 978-1-59454-134-6. 
  18. ^ a b Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 769–. ISBN 978-1-4511-4847-3. 
  19. ^ de Vries, Corinne S; Bromley, Susan E; Thomas, Hilary; Farmer, Richard D T (2005). "Tibolone and Endometrial Cancer". Drug Safety. 28 (3): 241–249. doi:10.2165/00002018-200528030-00005. ISSN 0114-5916. 
  20. ^ Berning, B.; Coelingh Bennink, H. J. T.; Fauser, B. C. J. M. (2009). "Tibolone and its effects on bone: a review". Climacteric. 4 (2): 120–136. doi:10.1080/cmt. ISSN 1369-7137. 

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