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Droloxifene

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Droloxifene
Clinical data
Other namesFK-435; ICI-79280; K-060; K-21060E; RP-60850; 3-Hydroxytamoxifen; 3-OH-TAM
Routes of
administration		Oral
Pharmacokinetic data
Eliminationhalf-life19–37 hours[1][2]
Identifiers
  • 3-[(E)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.102.640Edit this at Wikidata
Chemical and physical data
FormulaC26H29NO2
Molar mass387.523 g·mol−1
3D model (JSmol)
  • CC/C(=C(/C1=CC=C(C=C1)OCCN(C)C)\C2=CC(=CC=C2)O)/C3=CC=CC=C3
  • InChI=1S/C26H29NO2/c1-4-25(20-9-6-5-7-10-20)26(22-11-8-12-23(28)19-22)21-13-15-24(16-14-21)29-18-17-27(2)3/h5-16,19,28H,4,17-18H2,1-3H3/b26-25+
  • Key:ZQZFYGIXNQKOAV-OCEACIFDSA-N

Droloxifene (INN,USAN) (former developmental code namesFK-435,ICI-79280,K-060,K-21060E,RP-60850), also known as3-hydroxytamoxifen, is anonsteroidalselective estrogen receptor modulator (SERM) of thetriphenylethylene group[1] that was developed originally inGermany and later inJapan for the treatment ofbreast cancer,osteoporosis in men andpostmenopausal women, andcardiovascular disorders but was abandoned and never marketed.[3][4][5][6] It reachedphase II andphase IIIclinical 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 ananalogue oftamoxifen, specifically 3-hydroxytamoxifen, but has been said to have 10- to 60-fold increasedaffinity for theestrogen receptor[9] and reduced partialestrogenagonistic activity.[5][10] The affinity of droloxifene for the estrogen receptor ranges from 0.2 to 15.2% relative toestradiol 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 inluteinizing hormone andfollicle-stimulating hormone levels, indicating that it hasantigonadotropic activity, and dose-dependently increasessex hormone-binding globulin levels, indicating that it has estrogenic activity in theliver.[2] Similarly to tamoxifen, droloxifene has partial estrogenic effects in theuterus.[12] Unlike tamoxifen, droloxifene does not produceDNA adduct orliver tumors in animals.[2]

See also

[edit]

References

[edit]
  1. ^abOettel M, Schillinger E (6 December 2012).Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 158, 299.ISBN 978-3-642-60107-1.
  2. ^abcManni A (15 January 1999).Endocrinology of Breast Cancer. Springer Science & Business Media. pp. 298–.ISBN 978-1-59259-699-7.
  3. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 472–.ISBN 978-1-4757-2085-3.
  4. ^Morton IK, Hall JM (31 October 1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 106–.ISBN 978-0-7514-0499-9.
  5. ^abJordan VC, Furr BJ (5 February 2010).Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. pp. 200–.ISBN 978-1-59259-152-7.
  6. ^ab"Droloxifene".AdisInsight. Springer Nature Switzerland AG.
  7. ^abOttow E, Weinmann H (8 September 2008).Nuclear Receptors as Drug Targets. John Wiley & Sons. pp. 153–.ISBN 978-3-527-62330-3.
  8. ^Devita VT, Hellman S, Rosenberg SA (1 April 2003).Progress in Oncology 2003. Jones & Bartlett Learning. pp. 217–.ISBN 978-0-7637-2064-3.
  9. ^Missailidis S (13 October 2008).Anticancer Therapeutics. John Wiley & Sons. pp. 165–.ISBN 978-0-470-69703-0.
  10. ^Grese TA, Dodge JA (February 1998)."Selective estrogen receptor modulators (SERMs)".Current Pharmaceutical Design.4 (1): 71–92 (76).doi:10.2174/138161280401221007111005.PMID 10197034.S2CID 40919336.
  11. ^abWittliff JL, Kerr DA II, Andres SA (2005)."Estrogens IV: Estrogen-Like Pharmaceuticals". In Wexler, P. (ed.).Encyclopedia of Toxicology, 2nd Edition. Vol. Dib–L. Elsevier. pp. 254–258.ISBN 978-0-08-054800-5.
  12. ^Morrow M, Jordan VC (2003).Managing Breast Cancer Risk. PMPH-USA. pp. 193–.ISBN 978-1-55009-260-8.

External links

[edit]
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
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