(E)-4-Hydroxytamoxifen (Afimoxifene) is the less active isomer of 4-Hydroxytamoxifen. 4-Hydroxytamoxifen is the active metabolite of tamoxifen which is an anticancer drug and a SERM/selective estrogen receptor modulator.

Physicochemical Properties

Molecular Formula	C26H29NO2
Molecular Weight	387.51396
Exact Mass	387.22
Elemental Analysis	C, 80.59; H, 7.54; N, 3.61; O, 8.26
CAS #	174592-47-3
Related CAS #	4-Hydroxytamoxifen;68047-06-3;(E/Z)-4-Hydroxytamoxifen;68392-35-8; 174592-47-3 (E-isomer)
PubChem CID	5352135
Appearance	White to off-white solid powder
Density	1.092g/cm3
Boiling Point	514.4ºC at 760 mmHg
Flash Point	264.9ºC
Vapour Pressure	3.35E-11mmHg at 25°C
Index of Refraction	1.596
LogP	5.701
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	8
Heavy Atom Count	29
Complexity	493
Defined Atom Stereocenter Count	0
SMILES	OC1=CC=C(C=C1)/C(C2=CC=C(C=C2)OCCN(C)C)=C(CC)\C3=CC=CC=C3
InChi Key	TXUZVZSFRXZGTL-OCEACIFDSA-N
InChi Code	InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25+
Chemical Name	4-[(E)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
Synonyms	Afimoxifene; Afimoxifene, E-isomer; 68392-35-8; E-4-Hydroxytamoxifen; AKE3PH0IML; CHEMBL279301; (E)-4-Hydroxytamoxifen; cis-4-Hydroxytamoxifen; 4-((1E)-1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Estrogen Receptor/ERR
ln Vitro	Afimoxifene is a tamoxifen metabolite with both estrogenic and anti-estrogenic effects. Afimoxifene has a higher affinity for the estrogen receptor than tamoxifen, and functions as an antagonist in breast cancer cells.
ADME/Pharmacokinetics	Absorption, Distribution and Excretion Absorbed following topical application.
Additional Infomation	4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol is a stilbenoid. Afimoxifene (4-Hydroxytamoxifen, trade name TamoGel) is a new estrogen inhibitor under investigation for a variety of estrogen-dependent conditions, including cyclic breast pain and gynecomastia. TamoGel is formulated using Enhanced Hydroalcoholic Gel (EHG) Technology. This technology enables percutaneous delivery of drugs that cannot be delivered orally. It is being developed by Ascent Therapeutics. Afimoxifene is a tamoxifen metabolite with both estrogenic and anti-estrogenic effects. Afimoxifene has a higher affinity for the estrogen receptor than tamoxifen, and functions as an antagonist in breast cancer cells. Drug Indication For the potential treatment of menstrual-cycle related mastalgia, fibrocystic breast disease, breast disease, gynecomastia and Keloid scarring. Mechanism of Action Afimoxifene binds to estrogen receptors (ER), inducing a conformational change in the receptor. This results in a blockage or change in the expression of estrogen dependent genes.

Solubility Data

Solubility (In Vitro)

DMSO : ~12.5 mg/mL (~32.26 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 1.25 mg/mL (3.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (3.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 1.25 mg/mL (3.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.5806 mL	12.9029 mL	25.8058 mL
	5 mM	0.5161 mL	2.5806 mL	5.1612 mL
	10 mM	0.2581 mL	1.2903 mL	2.5806 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.