Chemistry:Droloxifene

From HandWiki
Short description: Chemical compound

Template:Cs1 config

Droloxifene
Droloxifene.svg
Clinical data
Other namesFK-435; ICI-79280; K-060; K-21060E; RP-60850; 3-Hydroxytamoxifen; 3-OH-TAM
Routes of
administration		Oral
Pharmacokinetic data
Elimination half-life19–37 hours[1][2]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC26H29NO2
Molar mass387.523 g·mol−1
3D model (JSmol)

Droloxifene (INN, USAN) (former developmental code names FK-435, ICI-79280, K-060, K-21060E, RP-60850), also known as 3-hydroxytamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group[1] that was developed originally in Germany and later in Japan for the treatment of breast cancer, osteoporosis in men and postmenopausal women, and cardiovascular disorders but was abandoned and never marketed.[3][4][5][6] It reached phase II and phase III clinical trials for these indications before development was discontinued in 2000.[6][7] The drug was found to be significantly less effective than tamoxifen in the treatment of breast cancer in two phase III clinical trials.[7][8]

Droloxifene is an analogue of tamoxifen, specifically 3-hydroxytamoxifen, but has been said to have 10- to 60-fold increased affinity for the estrogen receptor[9] and reduced partial estrogen agonistic activity.[5][10] The affinity of droloxifene for the estrogen receptor ranges from 0.2 to 15.2% relative to estradiol in different studies.[11] For comparison, the ranges are 0.06 to 16% for tamoxifen and 0.1 to 12% for clomifene.[11] Droloxifene causes a dose-dependent decrease in luteinizing hormone and follicle-stimulating hormone levels, indicating that it has antigonadotropic activity, and dose-dependently increases sex hormone-binding globulin levels, indicating that it has estrogenic activity in the liver.[2] Similarly to tamoxifen, droloxifene has partial estrogenic effects in the uterus.[12] Unlike tamoxifen, droloxifene does not produce DNA adduct or liver tumors in animals.[2]

See also

References

  1. ↑ 1.0 1.1 Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. 6 December 2012. pp. 158,299. ISBN 978-3-642-60107-1. https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA299. 
  2. ↑ 2.0 2.1 2.2 Endocrinology of Breast Cancer. Springer Science & Business Media. 15 January 1999. pp. 298–. ISBN 978-1-59259-699-7. https://books.google.com/books?id=7DSYBwAAQBAJ&pg=PA298. 
  3. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 472–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA472. 
  4. ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 31 October 1999. pp. 106–. ISBN 978-0-7514-0499-9. https://books.google.com/books?id=mqaOMOtk61IC&pg=PA106. 
  5. ↑ 5.0 5.1 Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. 5 February 2010. pp. 200–. ISBN 978-1-59259-152-7. https://books.google.com/books?id=dM0uvBnxiN0C&pg=PA200. 
  6. ↑ 6.0 6.1 "Droloxifene". AdisInsight. Springer Nature Switzerland AG. https://adisinsight.springer.com/drugs/800000847. 
  7. ↑ 7.0 7.1 Nuclear Receptors as Drug Targets. John Wiley & Sons. 8 September 2008. pp. 153–. ISBN 978-3-527-62330-3. https://books.google.com/books?id=iATfLbPgRugC&pg=PA153. 
  8. ↑ Progress in Oncology 2003. Jones & Bartlett Learning. 1 April 2003. pp. 217–. ISBN 978-0-7637-2064-3. https://books.google.com/books?id=4ipsRFlwlx0C&pg=PA217. 
  9. ↑ Anticancer Therapeutics. John Wiley & Sons. 13 October 2008. pp. 165–. ISBN 978-0-470-69703-0. https://books.google.com/books?id=BQOWmnxcaMwC&pg=PA165. 
  10. ↑ "Selective estrogen receptor modulators (SERMs)". Current Pharmaceutical Design 4 (1): 71–92 (76). February 1998. doi:10.2174/138161280401221007111005. PMID 10197034. https://books.google.com/books?id=dg4ropCtzJgC&pg=PA76. 
  11. ↑ 11.0 11.1 Wexler, P., ed (2005). "Estrogens IV: Estrogen-Like Pharmaceuticals". Encyclopedia of Toxicology, 2nd Edition. Dib-L. Elsevier. pp. 254–258. ISBN 978-0-08-054800-5. https://books.google.com/books?id=dEnbcGW44RYC&pg=PT3318. 
  12. ↑ Managing Breast Cancer Risk. PMPH-USA. 2003. pp. 193–. ISBN 978-1-55009-260-8. https://books.google.com/books?id=HXKibhaF5lMC&pg=PA193. 

External links



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Droloxifene&oldid=3421061"