N-Desmethyltamoxifen - Misplaced Pages

(Redirected from N-desmethyltamoxifen) Chemical compound Pharmaceutical compound

N-Desmethyltamoxifen
Clinical data

Other names	ICI-55,548; Nortamoxifen; NDMTAM
Drug class	Selective estrogen receptor modulator
Identifiers
IUPAC name 2-phenoxy]-N-methylethanamine
CAS Number	31750-48-8
PubChem CID	6378383
ChemSpider	2297759
UNII	OOJ759O35C
KEGG	C16546
ChEBI	CHEBI:80554
CompTox Dashboard (EPA)	DTXSID501315924
ECHA InfoCard	100.170.899
Chemical and physical data
Formula	C₂₅H₂₇NO
Molar mass	357.497 g·mol
3D model (JSmol)	Interactive image
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

N-Desmethyltamoxifen (developmental code name ICI-55,548) is a major metabolite of tamoxifen, a selective estrogen receptor modulator (SERM). 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. In one study, N-desmethyltamoxifen had an affinity for the estrogen receptor of 2.4% relative to estradiol. For comparison, tamoxifen, endoxifen, and afimoxifene (4-hydroxytamoxifen) had relative binding affinities of 2.8%, 181%, and 181%, respectively.

References

^ 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.
^ 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.
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.
^ 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.

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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