(E/Z) -4-Hydroxytamoxifen

(E/Z) -4-Hydroxytamoxifen (Afimoxifene) is a racemic compound of (Z) -4-Hydroxytamoxifen and (E) -4-Hydroxytamoxifen isomers. (E/Z) -4-Hydroxytamoxifen is a selective estrogen receptor modulator with mixed estrogenic and antiestrogenic activity, which is also an active metabolite of Tamoxifen (HY-13757A) . (E/Z) -4-Hydroxytamoxifen is an agonist of the G protein-coupled estrogen receptor (GPER) with relatively low affinity (100-1000 nM) . (E/Z) -4-Hydroxytamoxifen is promising for research of cyclical mastalgia, such as breast pain, tenderness, and nodularity[1][2][3][4].

Product Specifications

CAS Number

[68392-35-8]

Product Name Alternative

Afimoxifene; 4-OHT

UNSPSC

12352005

Hazard Statement

H225, H319

Target

Adhesion G Protein-coupled Receptors (AGPCRs) ; Drug Metabolite; Estrogen Receptor/ERR

Type

Reference compound

Related Pathways

GPCR/G Protein; Metabolic Enzyme/Protease; Vitamin D Related/Nuclear Receptor

Applications

Cancer-programmed cell death

Field of Research

Cancer; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/e-z-4-hydroxytamoxifen.html

Purity

99.62

Solubility

DMSO : 83.33 mg/mL (ultrasonic)

Smiles

OC1=CC=C(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)\CC)C=C1

Molecular Formula

C26H29NO2

Molecular Weight

387.51

Precautions

H225, H319

References & Citations

[1]Mansel R, et al. A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women. Breast Cancer Res Treat. 2007 Dec;106 (3) :389-97. |[2]Desta Z, et al. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310 (3) :1062-75.|[3]Gamboa da Costa G, et al. DNA adduct formation and mutant induction in Sprague-Dawley rats treated with tamoxifen and its derivatives. Carcinogenesis. 2001 Aug;22 (8) :1307-15. |[4]Prossnitz ER, et al. International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators. Pharmacol Rev. 2015 Jul;67 (3) :505-40.