Endoxifen

Endoxifen, also known as N-desmethyl-4-hydroxytamoxifen, is a chemical that is under development for estrogen receptor-positive breast cancer.[1] It is also being evaluated as an antipsychotic for treatment of mania and other psychotic disorders.[2]

Endoxifen
Clinical data
Other namesN-Desmethyl-4-hydroxytamoxifen; 4-Hydroxy-N-desmethyltamoxifen; Desmethylhydroxytamoxifen
Identifiers
CAS Number
  • 110025-28-0
    114828-90-9 (E-isomer)

    15917-65-4 (hydrochloride)
PubChem CID
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.208.548
Chemical and physical data
FormulaC25H27NO2
Molar mass373.496 g/mol g·mol−1
3D model (JSmol)

Endoxifen is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group. It is an active metabolite of tamoxifen and has been found to be effective in patients that have failed previous hormonal therapies (tamoxifen, aromatase inhibitors, and fulvestrant).[3][4][5] The prodrug tamoxifen is metabolized by the CYP2D6 enzyme to produce afimoxifene (4-hydroxytamoxifen) and endoxifen.[6]

See also

References
  1. "Z-endoxifen hydrochloride". NCI Drug Dictionary.
  2. Rankovic Z, Bingham M, Hargreaves R, eds. (2012). Drug Discovery for Psychiatric Disorders. Royal Society of Chemistry. p. 349. ISBN 978-1-84973-365-6.
  3. Hawse JR, Subramaniam M, Cicek M, Wu X, Gingery A, Grygo SB, Sun Z, Pitel KS, Lingle WL, Goetz MP, Ingle JN, Spelsberg TC (2013). "Endoxifen's molecular mechanisms of action are concentration dependent and different than that of other anti-estrogens". PLoS One. 8 (1): e54613. Bibcode:2013PLoSO...854613H. doi:10.1371/journal.pone.0054613. PMC 3557294. PMID 23382923. Lay summary – Medical Daily (December 12, 2013).
  4. Wu X, Hawse JR, Subramaniam M, Goetz MP, Ingle JN, Spelsberg TC (March 2009). "The tamoxifen metabolite, endoxifen, is a potent antiestrogen that targets estrogen receptor alpha for degradation in breast cancer cells". Cancer Research. 69 (5): 1722–7. doi:10.1158/0008-5472.CAN-08-3933. PMID 19244106.
  5. Gingery A, Subramaniam M, Pitel KS, Reese JM, Cicek M, Lindenmaier LB, Ingle JN, Goetz MP, Turner RT, Iwaniec UT, Spelsberg TC, Hawse JR (2014). "The effects of a novel hormonal breast cancer therapy, endoxifen, on the mouse skeleton". PLoS One. 9 (5): e98219. Bibcode:2014PLoSO...998219G. doi:10.1371/journal.pone.0098219. PMC 4031133. PMID 24853369.
  6. Wilcken N (2016). "Breast cancer: a disease of subtypes". Cancer Forum. 40 (3).


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