Afimoxifene, E-isomer
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540202

CAS#: 174592-47-3 (E-isomer)

Description: Afimoxifene, E-isomer, also called (E)-4-Hydroxytamoxifen, is a SERM and active metabolite of tamoxifen. The E isomer is less active thatn the Z isomer. It induces autophagy, vacuole formation and KRAS degradation in cancerl cells and decreases contractility in myocytes.

Chemical Structure

img
Afimoxifene, E-isomer
CAS# 174592-47-3 (E-isomer)
Instruction

Theoretical Analysis

MedKoo Cat#: 540202
Name: Afimoxifene, E-isomer
CAS#: 174592-47-3 (E-isomer)
Chemical Formula: C26H29NO2
Exact Mass: 387.22
Molecular Weight: 387.520
Elemental Analysis: C, 80.59; H, 7.54; N, 3.61; O, 8.26

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 Weeks
25mg USD 650 2 weeks
Bulk inquiry

Related CAS #: 68392-35-8   174592-47-3 (E-isomer)  

Synonym: (E)-4-Hydroxytamoxifen; cis-4-Hydroxytamoxifen; 4-((1E)-1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

IUPAC/Chemical Name: (E)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

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+

SMILES Code: OC1=CC=C(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)/CC)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 387.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Hui Y, Luo L, Zhang L, Kurogi K, Zhou C, Sakakibara Y, Suiko M, Liu MC. Sulfation of afimoxifene, endoxifen, raloxifene, and fulvestrant by the human cytosolic sulfotransferases (SULTs): A systematic analysis. J Pharmacol Sci. 2015 Jul;128(3):144-9. doi: 10.1016/j.jphs.2015.06.004. Epub 2015 Jun 25. PMID: 26169578.


2: Koo BK, Stange DE, Sato T, Karthaus W, Farin HF, Huch M, van Es JH, Clevers H. Controlled gene expression in primary Lgr5 organoid cultures. Nat Methods. 2011 Dec 4;9(1):81-3. doi: 10.1038/nmeth.1802. PMID: 22138822.


3: Mansel R, Goyal A, Nestour EL, Masini-Etévé V, O'Connell K; Afimoxifene (4-OHT) Breast Pain Research Group. 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. doi: 10.1007/s10549-007-9507-x. Epub 2007 Mar 10. PMID: 17351746.


4: Feil R, Wagner J, Metzger D, Chambon P. Regulation of Cre recombinase activity by mutated estrogen receptor ligand-binding domains. Biochem Biophys Res Commun. 1997 Aug 28;237(3):752-7. doi: 10.1006/bbrc.1997.7124. PMID: 9299439.


5: Link KH, Shi Y, Koh JT. Light activated recombination. J Am Chem Soc. 2005 Sep 28;127(38):13088-9. doi: 10.1021/ja0531226. PMID: 16173704; PMCID: PMC2512263.


6: Chen G, Yin S, Maiti S, Shao X. 4-Hydroxytamoxifen sulfation metabolism. J Biochem Mol Toxicol. 2002;16(6):279-85. doi: 10.1002/jbt.10048. PMID: 12481303.


7: Goetz MP, Loprinzi CL. A hot flash on tamoxifen metabolism. J Natl Cancer Inst. 2003 Dec 3;95(23):1734-5. doi: 10.1093/jnci/djg129. PMID: 14652227.


8: Walker AK, Enrietto PJ. Regulatable chimeric oncogenes. Methods Enzymol. 1995;254:469-80. doi: 10.1016/0076-6879(95)54032-6. PMID: 8531707.


9: Jordan VC, Allen KE, Dix CJ. Pharmacology of tamoxifen in laboratory animals. Cancer Treat Rep. 1980 Jun-Jul;64(6-7):745-59. PMID: 6775807.


10: Sasaki K, Terasaki M. Estrogen agonistic/antagonistic activity of brominated parabens. Environ Sci Pollut Res Int. 2018 Jul;25(21):21257-21266. doi: 10.1007/s11356-018-2600-3. Epub 2018 Jun 26. PMID: 29946845.


11: Gronemeyer H. Transcription activation by estrogen and progesterone receptors. Annu Rev Genet. 1991;25:89-123. doi: 10.1146/annurev.ge.25.120191.000513. PMID: 1667464.


12: Loren G, Espuny I, Llorente A, Donoghue C, Verdaguer X, Gomis RR, Riera A. Design and optimization of oestrogen receptor PROTACs based on 4-hydroxytamoxifen. Eur J Med Chem. 2022 Dec 5;243:114770. doi: 10.1016/j.ejmech.2022.114770. Epub 2022 Sep 14. PMID: 36148710.


13: Xiong W, Zhao JJ, Wang L, Jiang XH, Tao XQ. [Advances in the research of pharmacogenomics of tamoxifen]. Yao Xue Xue Bao. 2016 Sep;51(9):1356-67. Chinese. PMID: 29924509.


14: Cazzulino AS, Martinez R, Tomm NK, Denny CA. Improved specificity of hippocampal memory trace labeling. Hippocampus. 2016 Jun;26(6):752-62. doi: 10.1002/hipo.22556. Epub 2016 Jan 20. PMID: 26662713; PMCID: PMC4867142.


15: Stroemer P, Hope A, Patel S, Pollock K, Sinden J. Development of a human neural stem cell line for use in recovery from disability after stroke. Front Biosci. 2008 Jan 1;13:2290-2. doi: 10.2741/2842. PMID: 17981710.


16: Jordan VC. Metabolites of tamoxifen in animals and man: identification, pharmacology, and significance. Breast Cancer Res Treat. 1982;2(2):123-38. doi: 10.1007/BF01806449. PMID: 6184101.


17: Ransom RC, Foster DS, Salhotra A, Jones RE, Marshall CD, Leavitt T, Murphy MP, Moore AL, Blackshear CP, Brett EA, Wan DC, Longaker MT. Genetic dissection of clonal lineage relationships with hydroxytamoxifen liposomes. Nat Commun. 2018 Jul 30;9(1):2971. doi: 10.1038/s41467-018-05436-6. Erratum in: Nat Commun. 2018 Oct 19;9(1):4411. PMID: 30061668; PMCID: PMC6065311.


18: Ortiz J, Aranda FJ, Teruel JA, Ortiz A. Dissimilar action of tamoxifen and 4-hydroxytamoxifen on phosphatidylcholine model membranes. Biophys Chem. 2021 Nov;278:106681. doi: 10.1016/j.bpc.2021.106681. Epub 2021 Sep 9. PMID: 34530285.


19: Welsh J. Induction of apoptosis in breast cancer cells in response to vitamin D and antiestrogens. Biochem Cell Biol. 1994 Nov-Dec;72(11-12):537-45. doi: 10.1139/o94-072. PMID: 7654327.


20: Collins GA, Lipford JR, Deshaies RJ, Tansey WP. Gal4 turnover and transcription activation. Nature. 2009 Oct 8;461(7265):E7; discussion E8. doi: 10.1038/nature08406. PMID: 19812621; PMCID: PMC3072683.