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[[Sivifene]] (A-007) was initially thought to be a SERM due to its structural similarity to tamoxifen but it was subsequently found not to bind to the [[estrogen receptor]] (ER).<ref name="EilenderLoRusso2005">{{cite journal|last1=Eilender|first1=David|last2=LoRusso|first2=Patricia|last3=Thomas|first3=Leonard|last4=McCormick|first4=Catherine|last5=Rodgers|first5=Andrew H.|last6=Hooper|first6=Catherine L.|last7=Tornyos|first7=Karl|last8=Krementz|first8=Edward T.|last9=Parker|first9=Steven|last10=Morgan|first10=Lee Roy|title=4,4′-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007): a topical treatment for cutaneous metastases from malignant cancers|journal=Cancer Chemotherapy and Pharmacology|volume=57|issue=6|year=2005|pages=719–726|issn=0344-5704|doi=10.1007/s00280-005-0124-2}}</ref> [[Tesmilifene]] (DPPE; YMB-1002, BMS-217380-01) is also structurally related to tamoxifen but similarly does not bind to the ER and is not a SERM.<ref name="pmid18480139">{{cite journal | vauthors = Brandes LJ | title = N,N-diethyl-2-[4-(phenylmethyl) phenoxy] ethanamine (DPPE; tesmilifene), a chemopotentiating agent with hormetic effects on DNA synthesis in vitro, may improve survival in patients with metastatic breast cancer | journal = Hum Exp Toxicol | volume = 27 | issue = 2 | pages = 143–7 | year = 2008 | pmid = 18480139 | doi = 10.1177/0960327108090751 | url = }}</ref><ref name="pmid6548377">{{cite journal | vauthors = Brandes LJ, Hermonat MW | title = A diphenylmethane derivative specific for the antiestrogen binding site found in rat liver microsomes | journal = Biochem. Biophys. Res. Commun. | volume = 123 | issue = 2 | pages = 724–8 | year = 1984 | pmid = 6548377 | doi = | url = }}</ref>
[[Sivifene]] (A-007) was initially thought to be a SERM due to its structural similarity to tamoxifen but it was subsequently found not to bind to the [[estrogen receptor]] (ER).<ref name="EilenderLoRusso2005">{{cite journal|last1=Eilender|first1=David|last2=LoRusso|first2=Patricia|last3=Thomas|first3=Leonard|last4=McCormick|first4=Catherine|last5=Rodgers|first5=Andrew H.|last6=Hooper|first6=Catherine L.|last7=Tornyos|first7=Karl|last8=Krementz|first8=Edward T.|last9=Parker|first9=Steven|last10=Morgan|first10=Lee Roy|title=4,4′-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007): a topical treatment for cutaneous metastases from malignant cancers|journal=Cancer Chemotherapy and Pharmacology|volume=57|issue=6|year=2005|pages=719–726|issn=0344-5704|doi=10.1007/s00280-005-0124-2}}</ref> [[Tesmilifene]] (DPPE; YMB-1002, BMS-217380-01) is also structurally related to tamoxifen but similarly does not bind to the ER and is not a SERM.<ref name="pmid18480139">{{cite journal | vauthors = Brandes LJ | title = N,N-diethyl-2-[4-(phenylmethyl) phenoxy] ethanamine (DPPE; tesmilifene), a chemopotentiating agent with hormetic effects on DNA synthesis in vitro, may improve survival in patients with metastatic breast cancer | journal = Hum Exp Toxicol | volume = 27 | issue = 2 | pages = 143–7 | year = 2008 | pmid = 18480139 | doi = 10.1177/0960327108090751 | url = }}</ref><ref name="pmid6548377">{{cite journal | vauthors = Brandes LJ, Hermonat MW | title = A diphenylmethane derivative specific for the antiestrogen binding site found in rat liver microsomes | journal = Biochem. Biophys. Res. Commun. | volume = 123 | issue = 2 | pages = 724–8 | year = 1984 | pmid = 6548377 | doi = | url = }}</ref>

==Structure==
SERMs can be variously classified [[chemical structure|structurally]] as [[triphenylethylene]]s (tamoxifen, clomifene, toremifene, droloxifene, idoxifene, ospemifene, fispemifene, afimoxifene, others), [[benzothiophene]]s (raloxifene, arzoxifene), [[indole]]s (bazedoxifene, zindoxifene, pipendoxifene), [[tetrahydronaphthalene]]s (lasofoxifene, nafoxidine), and [[benzopyran]]s (acolbifene, ormeloxifene, levormeloxifene).<ref name="BilezikianRaisz2008">{{cite book|author1=John P. Bilezikian|author2=Lawrence G. Raisz|author3=T. John Martin|title=Principles of Bone Biology|url=https://books.google.com/books?id=LEDkfnAIjdkC&pg=PA891|date=29 September 2008|publisher=Academic Press|isbn=978-0-08-056875-1|pages=891–}}</ref><ref name="SilvermanAbrahamsen2015">{{cite book|author1=Stuart Silverman|author2=Bo Abrahamsen|title=The Duration and Safety of Osteoporosis Treatment: Anabolic and Antiresorptive Therapy|url=https://books.google.com/books?id=5bFPCwAAQBAJ&pg=PA24|date=29 December 2015|publisher=Springer|isbn=978-3-319-23639-1|pages=24–}}</ref><ref name="RahmanZaman2014">{{cite book|author1=Atta-ur Rahman|author2=Khurshid Zaman|title=Topics in Anti-Cancer Research|url=https://books.google.com/books?id=G0dsDgAAQBAJ&pg=PA559|date=28 November 2014|publisher=Bentham Science Publishers|isbn=978-1-60805-908-9|pages=559–565}}</ref>


==See also==
==See also==
Line 15: Line 18:


==References==
==References==
{{reflist|30em}}
{{Reflist|30em}}


{{Estrogens and antiestrogens}}
{{Estrogens and antiestrogens}}

Revision as of 04:13, 27 November 2017

Tamoxifen, the most well-known and widely used SERM.

This is a list of selective estrogen receptor modulators (SERMs).

Approved

SERMs that have been approved for medical use include bazedoxifene (+conjugated estrogens (Duavee)), broparestrol (Acnestrol), clomifene (Clomid), cyclofenil (Sexovid), lasofoxifene (Fablyn), ormeloxifene (Centron, Novex, Novex-DS, Sevista), ospemifene (Osphena; deaminohydroxytoremifene), raloxifene (Evista), tamoxifen (Nolvadex), and toremifene (Fareston; 4-chlorotamoxifen).[1]

Non-approved

SERMs that have not been approved for medical use include acolbifene, afimoxifene (4-hydroxytamoxifen; metabolite of tamoxifen), arzoxifene, brilanestrant, clomifenoxide (clomiphene N-oxide; metabolite of clomifene),[2] droloxifene (3-hydroxytamoxifen), elacestrant, enclomifene ((E)-clomifene), endoxifen (4-hydroxy-N-desmethyltamoxifen; metabolite of tamoxifen), etacstil, fispemifene, GW-7604 (4-hydroxyetacstil; metabolite of etacstil), idoxifene (pyrrolidino-4-iodotamoxifen), levormeloxifene ((L)-ormeloxifene), miproxifene, nafoxidine, nitromifene (CI-628), panomifene, pipendoxifene (ERA-923), trioxifene, zindoxifene (D-16726), and zuclomifene ((Z)-clomifene).[3][1][4][5][6]

Sivifene (A-007) was initially thought to be a SERM due to its structural similarity to tamoxifen but it was subsequently found not to bind to the estrogen receptor (ER).[7] Tesmilifene (DPPE; YMB-1002, BMS-217380-01) is also structurally related to tamoxifen but similarly does not bind to the ER and is not a SERM.[8][9]

Structure

SERMs can be variously classified structurally as triphenylethylenes (tamoxifen, clomifene, toremifene, droloxifene, idoxifene, ospemifene, fispemifene, afimoxifene, others), benzothiophenes (raloxifene, arzoxifene), indoles (bazedoxifene, zindoxifene, pipendoxifene), tetrahydronaphthalenes (lasofoxifene, nafoxidine), and benzopyrans (acolbifene, ormeloxifene, levormeloxifene).[10][11][12]

See also

References

  1. ^ a b Pinkerton, JoAnn V.; Thomas, Semara (2014). "Use of SERMs for treatment in postmenopausal women". The Journal of Steroid Biochemistry and Molecular Biology. 142: 142–154. doi:10.1016/j.jsbmb.2013.12.011. ISSN 0960-0760.
  2. ^ Analytical Profiles of Drug Substances and Excipients. Academic Press. 20 March 1998. pp. 112–113. ISBN 978-0-08-086120-3.
  3. ^ World Health Organization (2013), The use of stems in the selection of International Nonproprietary Names (INN)for pharmaceutical substances (PDF)
  4. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3.
  5. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  6. ^ Taylor, Hugh S. (2009). "Designing the ideal selective estrogen receptor modulator-an achievable goal?". Menopause. 16 (3): 609–615. doi:10.1097/gme.0b013e3181906fa3. ISSN 1072-3714.
  7. ^ Eilender, David; LoRusso, Patricia; Thomas, Leonard; McCormick, Catherine; Rodgers, Andrew H.; Hooper, Catherine L.; Tornyos, Karl; Krementz, Edward T.; Parker, Steven; Morgan, Lee Roy (2005). "4,4′-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007): a topical treatment for cutaneous metastases from malignant cancers". Cancer Chemotherapy and Pharmacology. 57 (6): 719–726. doi:10.1007/s00280-005-0124-2. ISSN 0344-5704.
  8. ^ Brandes LJ (2008). "N,N-diethyl-2-[4-(phenylmethyl) phenoxy] ethanamine (DPPE; tesmilifene), a chemopotentiating agent with hormetic effects on DNA synthesis in vitro, may improve survival in patients with metastatic breast cancer". Hum Exp Toxicol. 27 (2): 143–7. doi:10.1177/0960327108090751. PMID 18480139.
  9. ^ Brandes LJ, Hermonat MW (1984). "A diphenylmethane derivative specific for the antiestrogen binding site found in rat liver microsomes". Biochem. Biophys. Res. Commun. 123 (2): 724–8. PMID 6548377.
  10. ^ John P. Bilezikian; Lawrence G. Raisz; T. John Martin (29 September 2008). Principles of Bone Biology. Academic Press. pp. 891–. ISBN 978-0-08-056875-1.
  11. ^ Stuart Silverman; Bo Abrahamsen (29 December 2015). The Duration and Safety of Osteoporosis Treatment: Anabolic and Antiresorptive Therapy. Springer. pp. 24–. ISBN 978-3-319-23639-1.
  12. ^ Atta-ur Rahman; Khurshid Zaman (28 November 2014). Topics in Anti-Cancer Research. Bentham Science Publishers. pp. 559–565. ISBN 978-1-60805-908-9.


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