Tibolone: Difference between revisions

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Tibolone
Clinical data
Synonyms	(7α,17β)-17-ethynyl-17-hydroxy-7-methylestr-5(10)-en-3-one
AHFS/Drugs.com	International Drug Names
Pregnancy; category	ADEC Category D;
Routes of; administration	oral
ATC code	G03CX01 (WHO) ;
Identifiers
	IUPAC name 17-Hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3-one;
CAS Number	5630-53-5 ;
PubChem CID	444008;
ChemSpider	392038 ;
UNII	FF9X0205V2;
KEGG	D01639 ;
ChEBI	CHEBI:32223 ;
ChEMBL	ChEMBL1558898 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C21H28O2
Molar mass	312.446 g/mol
3D model (JSmol)	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 ; Key:WZDGZWOAQTVYBX-XOINTXKNSA-N ;
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Revision as of 13:00, 9 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Tibolone is a synthetic steroid hormone drug, which is fairly non-selective in its binding profile, acting as an agonist mainly at estrogen receptors, with a preference for ER alpha.^[1] It is used mainly for treatment of endometriosis,^[2] 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.^[3]^[4]^[5] It has also been investigated as a possible treatment for female sexual dysfunction.^[6]

Adverse 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.^[7]

References

↑ 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.
↑ 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 (Online) (1): CD005997. doi:10.1002/14651858.CD005997.pub2. PMID 19160262.
↑ 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.
↑ 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 2544356. PMID 18488873.
↑ 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.
↑ 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.
↑ "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.

Template:Estrogens Template:Progestogens Template:Sex steroidergics

[pmid19464167-1] 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.

[pmid19160262-2] 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 (Online) (1): CD005997. doi:10.1002/14651858.CD005997.pub2. PMID 19160262.

[pmid18377345-3] 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.

[pmid18488873-4] 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 2544356. PMID 18488873.

[pmid19317264-5] 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.

[6] 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.

[7] "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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

@@ Line 1: / Line 1: @@
-{{Drugbox|
+{{Drugbox
-|IUPAC_name = 17-Hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3-one
+| Verifiedfields = changed
-| image= Tibolone.png
+| verifiedrevid = 470610138
-| CAS_number=5630-53-5
+| IUPAC_name = 17-Hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3-one
-| ATC_prefix=G03
+| image = Tibolone Structural Formulae V.1.png
-| ATC_suffix=DC05
-| ATC_supplemental=
+<!--Clinical data-->
-| PubChem=21844
+| tradename =
-| DrugBank=
+| Drugs.com = {{drugs.com|international|tibolone}}
-| C = 21 | H = 28 | O = 2
+| pregnancy_category = ADEC Category D
+| legal_status =
+| routes_of_administration = oral
+<!--Pharmacokinetic data-->
+| bioavailability =
+| metabolism =
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 5630-53-5
+| ATC_prefix = G03
+| ATC_suffix = CX01
+| PubChem = 444008
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 392038
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = FF9X0205V2
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D01639
+| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI = 32223
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1558898
+<!--Chemical data-->
+| C=21 | H=28 | O=2
 | molecular_weight = 312.446 g/mol
-| bioavailability=
+| 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
-| metabolism =
+| InChI = 1/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
-| elimination_half-life=
+| InChIKey = WZDGZWOAQTVYBX-XOINTXKNBA
-| excretion =
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| pregnancy_category =
+| StdInChI = 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
-| legal_status =
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| routes_of_administration=
+| StdInChIKey = WZDGZWOAQTVYBX-XOINTXKNSA-N
+| synonyms = <small>(7α,17β)-17-ethynyl-17-hydroxy-7-methylestr-5(10)-en-3-one</small>
 }}
+__Notoc__
 {{SI}}
+{{CMG}}
+==Overview==
+'''Tibolone''' is a synthetic [[steroid hormone]] drug, which is fairly non-selective in its binding profile, acting as an [[agonist]] mainly at [[estrogen receptor]]s, with a preference for ER alpha.<ref name="pmid19464167">{{cite journal |author=Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, Balaguer P, Maudelonde T |title=Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites |journal=The Journal of Steroid Biochemistry and Molecular Biology |volume=116 |issue=1–2 |pages=8–14 |date=August 2009 |pmid=19464167 |doi=10.1016/j.jsbmb.2009.03.008 |url=}}</ref> It is used mainly for treatment of [[endometriosis]],<ref name="pmid19160262">{{cite journal |author=Al Kadri H, Hassan S, Al-Fozan HM, Hajeer A |editor1-last=Al Kadri |editor1-first=Hanan |title=Hormone therapy for endometriosis and surgical menopause |journal=Cochrane Database of Systematic Reviews (Online) |volume= |issue=1 |pages=CD005997 |year=2009 |pmid=19160262 |doi=10.1002/14651858.CD005997.pub2 |url=}}</ref> as well as [[Hormone replacement therapy (menopause)|hormone replacement therapy]] in [[menopause|post-menopausal]] women. Tibolone has similar or greater efficacy compared to older hormone replacement drugs, but shares a similar side effect profile.<ref name="pmid18377345">{{cite journal |author=Lazovic G, Radivojevic U, Marinkovic J |title=Tibolone: the way to beat many a postmenopausal ailments |journal=Expert Opinion on Pharmacotherapy |volume=9 |issue=6 |pages=1039–47 |date=April 2008 |pmid=18377345 |doi=10.1517/14656566.9.6.1039 |url=}}</ref><ref name="pmid18488873">{{cite journal |author=Garefalakis M, Hickey M |title=Role of androgens, progestins and tibolone in the treatment of menopausal symptoms: a review of the clinical evidence |journal=Clinical Interventions in Aging |volume=3 |issue=1 |pages=1–8 |year=2008 |pmid=18488873 |pmc=2544356 |doi= |url=}}</ref><ref name="pmid19317264">{{cite journal |author=Vavilis D, Zafrakas M, Goulis DG, Pantazis K, Agorastos T, Bontis JN |title=Hormone therapy for postmenopausal breast cancer survivors: a survey among obstetrician-gynaecologists |journal=European Journal of Gynaecological Oncology |volume=30 |issue=1 |pages=82–4 |year=2009 |pmid=19317264 |doi= |url=}}</ref> It has also been investigated as a possible treatment for [[female sexual dysfunction]].<ref>{{cite journal | pmid = 19731119 | year = 2010 | last1 = Ziaei | first1 = S | last2 = Moghasemi | first2 = M | last3 = Faghihzadeh | first3 = S | title = Comparative effects of conventional hormone replacement therapy and tibolone on climacteric symptoms and sexual dysfunction in postmenopausal women | volume = 13 | issue = 2 | pages = 147–56 | doi = 10.1080/13697130903009195 | journal = Climacteric : the journal of the International Menopause Society}}</ref>
+==Adverse 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.<ref>{{cite web| url=http://archive.ahrq.gov/news/newsroom/press-releases/2009/brcanmed.html| title=Medications Effective in Reducing Risk of Breast Cancer But Increase Risk of Adverse Effects, New Report Says| publisher=U.S. Department of Health & Human Services - Agency for Healthcare Research and Quality| date=September 2009|accessdate=2 June 2014}}</ref>
+==References==
+{{Reflist|2}}
-==Overview==
-'''Tibolone''' is a synthetic [[hormone]]-type drug. It is used mainly for [[hormone replacement therapy]] in [[menopause|post-menopausal]] women.
-{{Sex hormones}}
+{{Estrogens}}
+{{Progestogens}}
+{{Sex steroidergics}}
-[[Category:Progestagens]]
+[[Category:Drug]]
+[[Category:Progestogens]]
 [[Category:Hormonal agents]]
 [[Category:Steroid hormones]]
-[[Category:Endocrinology]]
+[[Category:Schering-Plough]]
-[[pt:Tibolona]]
+[[Category:Female sexual dysfunction drugs]]
-{{WikiDoc Help Menu}}
-{{WikiDoc Sources}}

Tibolone: Difference between revisions

Revision as of 13:00, 9 April 2015

Overview

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References

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