N-Desmethyltamoxifen

N-Desmethyltamoxifen is the major metabolite of tamoxifen in humans. N-Desmethyltamoxifen, a poor antiestrogen, is a ten-fold more potent protein kinase C (PKC) inhibitor than Tamoxifen. N-Desmethyltamoxifen is also a potent regulator of ceramide metabolism in human AML cells, limiting ceramide glycosylation, hydrolysis, and sphingosine phosphorylation[1][2][3].

Product Specifications

CAS Number

[31750-48-8]

UNSPSC

12352005

Hazard Statement

H302-H350-H360-H372

Target

Drug Metabolite; Endogenous Metabolite; Estrogen Receptor/ERR; PKC

Type

Reference compound

Related Pathways

Epigenetics; Metabolic Enzyme/Protease; TGF-beta/Smad; Vitamin D Related/Nuclear Receptor

Applications

Cancer-Kinase/protease

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/n-desmethyltamoxifen.html

Solubility

10 mM in DMSO

Smiles

CC/C(C1=CC=CC=C1)=C(C2=CC=C(OCCNC)C=C2)\C3=CC=CC=C3

Molecular Formula

C25H27NO

Molecular Weight

357.50

Precautions

P260-P264-P270-P280-P330-P405-P501

References & Citations

[1]Vertosick FT Jr, et al. A comparison of the relative chemosensitivity of human gliomas to tamoxifen and n-desmethyltamoxifen in vitro. J Neurooncol. 1994;19 (2) :97-103.|[2]Morad SA, et al. Modification of sphingolipid metabolism by tamoxifen and N-desmethyltamoxifen in acute myelogenous leukemia--Impact on enzyme activity and response to cytotoxics. Biochim Biophys Acta. 2015 Jul;1851 (7) :919-28.|[3]Reddel RR, et al. N-desmethyltamoxifen inhibits growth of MCF 7 human mammary carcinoma cells in vitro. Eur J Cancer Clin Oncol. 1983 Aug;19 (8) :1179-81.|[4]Seong Hwan Kim, et al. Use of Antidepressants in Patients with Breast Cancer Taking Tamoxifen. J Breast Cancer. 2010 Dec;13 (4) :325-336.