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'''Zuclomifene''' ([[International Nonproprietary Name|INN]]; or '''zuclomiphene''' ([[United States Adopted Name|USAN]])) is a [[nonsteroidal]] [[selective estrogen receptor modulator]] (SERM) of the [[triphenylethylene]] group that was never marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA298|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=298–}}</ref><ref name="MortonHall1999">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=mqaOMOtk61IC&pg=PA79|date=31 October 1999|publisher=Springer Science & Business Media|isbn=978-0-7514-0499-9|pages=79–}}</ref><ref name="AdisInsight">{{cite web | url = http://adisinsight.springer.com/drugs/800019625 | title = Enclomifene - Repros Therapeutics | publisher = Adis Insight}}</ref><ref name="pmid19204885">{{cite journal | vauthors = Hill S, Arutchelvam V, Quinton R | title = Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men | journal = IDrugs | volume = 12 | issue = 2 | pages = 109–19 | year = 2009 | pmid = 19204885 | doi = | url = https://www.researchgate.net/publication/23995306}}</ref> It is one of the two [[stereoisomer]]s of [[clomifene]], which itself is a mixture of 38% zuclomifene and 62% [[enclomifene]].<ref name="pmid19204885" /> Zuclomifene is the (''Z'')-stereoisomer of clomifene, while enclomifene is the (''E'')-stereoisomer.<ref name="Elks2014" /><ref name="MortonHall1999" /> Whereas zuclomifene is described as mildly [[estrogen]]ic, enclomifene is described as [[antiestrogen]]ic.<ref name="pmid19204885" /><ref name="FischerGanellin2012">{{cite book|author1=Janos Fischer|author2=C. Robin Ganellin|author3=David P. Rotella|title=Analogue-based Drug Discovery III|url=https://books.google.com/books?id=BP2Bo11gTOMC&pg=SA5-PA58|date=15 October 2012|publisher=John Wiley & Sons|isbn=978-3-527-65110-8|pages=5–}}</ref> In accordance, unlike [[enclomifene]], zuclomifene is [[antigonadotropic]] due to activation of the estrogen receptor and reduces testosterone levels in men.<ref name="pmid19204885" /> It is also about five times more potent than enclomifene in [[ovulation induction|inducing ovulation]].<ref name="FischerGanellin2012" />
'''Zuclomifene''' ([[International Nonproprietary Name|INN]]; or '''zuclomiphene''' ([[United States Adopted Name|USAN]])) is a [[nonsteroidal]] [[selective estrogen receptor modulator]] (SERM) of the [[triphenylethylene]] group that was never marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA298|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=298–}}</ref><ref name="MortonHall1999">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=mqaOMOtk61IC&pg=PA79|date=31 October 1999|publisher=Springer Science & Business Media|isbn=978-0-7514-0499-9|pages=79–}}</ref><ref name="AdisInsight">{{cite web | url = http://adisinsight.springer.com/drugs/800019625 | title = Enclomifene - Repros Therapeutics | publisher = Adis Insight}}</ref><ref name="pmid19204885">{{cite journal | vauthors = Hill S, Arutchelvam V, Quinton R | title = Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men | journal = IDrugs | volume = 12 | issue = 2 | pages = 109–19 | year = 2009 | pmid = 19204885 | url = https://www.researchgate.net/publication/23995306}}</ref> It is one of the two [[stereoisomer]]s of [[clomifene]], which itself is a mixture of 38% zuclomifene and 62% [[enclomifene]].<ref name="pmid19204885" /> Zuclomifene is the (''Z'')-stereoisomer of clomifene, while enclomifene is the (''E'')-stereoisomer.<ref name="Elks2014" /><ref name="MortonHall1999" /> Whereas zuclomifene is described as mildly [[estrogen]]ic, enclomifene is described as [[antiestrogen]]ic.<ref name="pmid19204885" /><ref name="FischerGanellin2012">{{cite book|author1=Janos Fischer|author2=C. Robin Ganellin|author3=David P. Rotella|title=Analogue-based Drug Discovery III|url=https://books.google.com/books?id=BP2Bo11gTOMC&pg=SA5-PA58|date=15 October 2012|publisher=John Wiley & Sons|isbn=978-3-527-65110-8|pages=5–}}</ref> In accordance, unlike [[enclomifene]], zuclomifene is [[antigonadotropic]] due to activation of the estrogen receptor and reduces testosterone levels in men.<ref name="pmid19204885" /> It is also about five times more potent than enclomifene in [[ovulation induction|inducing ovulation]].<ref name="FischerGanellin2012" />


==References==
==References==

Revision as of 05:20, 3 December 2020

Zuclomifene
Clinical data
Other namesZuclomiphene; trans-Clomifene; Transclomiphene; (Z)-Clomifene; ICI-46476; RMI-16312; Zuclomifene citrate; Zuclomiphene citrate
Routes of
administration		Oral
Identifiers
  • 2-[4-[(Z)-2-Chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H28ClNO
Molar mass405.97 g·mol−1
3D model (JSmol)
  • CCN(CC)CCOC1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\Cl)/C3=CC=CC=C3
  • InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25-
  • Key:GKIRPKYJQBWNGO-QPLCGJKRSA-N

Zuclomifene (INN; or zuclomiphene (USAN)) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was never marketed.[1][2][3][4] It is one of the two stereoisomers of clomifene, which itself is a mixture of 38% zuclomifene and 62% enclomifene.[4] Zuclomifene is the (Z)-stereoisomer of clomifene, while enclomifene is the (E)-stereoisomer.[1][2] Whereas zuclomifene is described as mildly estrogenic, enclomifene is described as antiestrogenic.[4][5] In accordance, unlike enclomifene, zuclomifene is antigonadotropic due to activation of the estrogen receptor and reduces testosterone levels in men.[4] It is also about five times more potent than enclomifene in inducing ovulation.[5]

References

  1. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 298–. ISBN 978-1-4757-2085-3.
  2. ^ a b I.K. Morton; Judith M. Hall (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 79–. ISBN 978-0-7514-0499-9.
  3. ^ "Enclomifene - Repros Therapeutics". Adis Insight.
  4. ^ a b c d Hill S, Arutchelvam V, Quinton R (2009). "Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men". IDrugs. 12 (2): 109–19. PMID 19204885.
  5. ^ a b Janos Fischer; C. Robin Ganellin; David P. Rotella (15 October 2012). Analogue-based Drug Discovery III. John Wiley & Sons. pp. 5–. ISBN 978-3-527-65110-8.


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