N-Desmethyltamoxifen

N-Desmethyltamoxifen (developmental code name ICI-55,548) is a major metabolite of tamoxifen, a selective estrogen receptor modulator (SERM).[1][2] N-Desmethyltamoxifen is further metabolized into endoxifen (4-hydroxy-N-desmethyltamoxifen), which is thought to be the major active form of tamoxifen in the body.[1][2][3] In one study, N-desmethyltamoxifen had an affinity for the estrogen receptor of 2.4% relative to estradiol.[4] For comparison, tamoxifen, endoxifen, and afimoxifene (4-hydroxytamoxifen) had relative binding affinities of 2.8%, 181%, and 181%, respectively.[4]

N-Desmethyltamoxifen
Clinical data
Other namesICI-55,548; Nortamoxifen; NDMTAM
Drug classSelective estrogen receptor modulator
Identifiers
IUPAC name
  • 2-[4-[(Z)-1,2-Diphenylbut-1-enyl]phenoxy]-N-methylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ECHA InfoCard100.170.899
Chemical and physical data
FormulaC25H27NO
Molar mass357.497 g·mol−1
3D model (JSmol)
SMILES
  • CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCNC)/C3=CC=CC=C3
InChI
  • InChI=1S/C25H27NO/c1-3-24(20-10-6-4-7-11-20)25(21-12-8-5-9-13-21)22-14-16-23(17-15-22)27-19-18-26-2/h4-17,26H,3,18-19H2,1-2H3/b25-24-
  • Key:NYDCDZSEEAUOHN-IZHYLOQSSA-N

References
  1. Sanchez-Spitman AB, Swen JJ, Dezentje VO, Moes DJ, Gelderblom H, Guchelaar HJ (June 2019). "Clinical pharmacokinetics and pharmacogenetics of tamoxifen and endoxifen". Expert Review of Clinical Pharmacology. 12 (6): 523–536. doi:10.1080/17512433.2019.1610390. PMID 31008668.
  2. Klein DJ, Thorn CF, Desta Z, Flockhart DA, Altman RB, Klein TE (November 2013). "PharmGKB summary: tamoxifen pathway, pharmacokinetics". Pharmacogenet Genomics. 23 (11): 643–7. doi:10.1097/FPC.0b013e3283656bc1. PMC 4084801. PMID 23962908.
  3. Binkhorst L, Mathijssen RH, Jager A, van Gelder T (March 2015). "Individualization of tamoxifen therapy: much more than just CYP2D6 genotyping". Cancer Treat Rev. 41 (3): 289–99. doi:10.1016/j.ctrv.2015.01.002. PMID 25618289.
  4. Maximov PY, McDaniel RE, Fernandes DJ, Bhatta P, Korostyshevskiy VR, Curpan RF, Jordan VC (October 2014). "Pharmacological relevance of endoxifen in a laboratory simulation of breast cancer in postmenopausal patients". J Natl Cancer Inst. 106 (10). doi:10.1093/jnci/dju283. PMC 4271116. PMID 25258390.



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