List of selective estrogen receptor modulators explained

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

Approved

SERMs that have been approved for medical use include anordrin (+mifepristone (Zi Yun)), 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]

Clinical trials

SERMs that are currently under development and in clinical trials include acolbifene, afimoxifene (4-hydroxytamoxifen; metabolite of tamoxifen), elacestrant, enclomifene ((E)-clomifene), endoxifen (4-hydroxy-N-desmethyltamoxifen; metabolite of tamoxifen), and zuclomifene ((Z)-clomifene).[2]

Non-approved

SERMs that have not been approved for medical use include arzoxifene, brilanestrant, clomifenoxide (clomiphene N-oxide; metabolite of clomifene),[3] droloxifene (3-hydroxytamoxifen), etacstil, fispemifene, GW-7604 (4-hydroxyetacstil; metabolite of etacstil), idoxifene (pyrrolidino-4-iodotamoxifen), levormeloxifene ((L)-ormeloxifene), miproxifene, nafoxidine, nitromifene (CI-628), NNC 45-0095, panomifene, pipendoxifene (ERA-923), trioxifene, and zindoxifene (D-16726).[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]

Notes and References

  1. Pinkerton. JoAnn V.. Thomas. Semara. Use of SERMs for treatment in postmenopausal women. The Journal of Steroid Biochemistry and Molecular Biology. 142. 2014. 142–154. 0960-0760. 10.1016/j.jsbmb.2013.12.011. 24373794. 24196362.
  2. Web site: Home - AdisInsight . adisinsight.springer.com.
  3. Book: Analytical Profiles of Drug Substances and Excipients. 20 March 1998. Academic Press. 978-0-08-086120-3. 112–113.
  4. Book: J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3.
  5. Book: I.K. Morton. Judith M. Hall. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012. Springer Science & Business Media. 978-94-011-4439-1.
  6. Taylor. Hugh S.. Designing the ideal selective estrogen receptor modulator-an achievable goal?. Menopause. 16. 3. 2009. 609–615. 1072-3714. 10.1097/gme.0b013e3181906fa3. 3107842. 19182697.
  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. 4,4′-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007): a topical treatment for cutaneous metastases from malignant cancers. Cancer Chemotherapy and Pharmacology. 57. 6. 2005. 719–726. 0344-5704. 10.1007/s00280-005-0124-2. 16184382. 10830366.
  8. Brandes LJ . 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 . 2008 . 18480139 . 10.1177/0960327108090751 . 20966915 . free .
  9. Brandes LJ, Hermonat MW . A diphenylmethane derivative specific for the antiestrogen binding site found in rat liver microsomes . Biochem. Biophys. Res. Commun. . 123 . 2 . 724–8 . 1984 . 6548377 . 10.1016/0006-291x(84)90289-4.
  10. Book: John P. Bilezikian. Lawrence G. Raisz. T. John Martin. Principles of Bone Biology. 29 September 2008. Academic Press. 978-0-08-056875-1. 891–.
  11. Book: Stuart Silverman. Bo Abrahamsen. The Duration and Safety of Osteoporosis Treatment: Anabolic and Antiresorptive Therapy. 29 December 2015. Springer. 978-3-319-23639-1. 24–.
  12. Book: Atta-ur Rahman. Khurshid Zaman. Topics in Anti-Cancer Research. 28 November 2014. Bentham Science Publishers. 978-1-60805-908-9. 559–565.

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