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MedKoo Cat#: 540202 | Name: Afimoxifene, E-isomer
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Description:

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

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

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

Theoretical Analysis

MedKoo Cat#: 540202

Name: Afimoxifene, E-isomer

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

Chemical Formula: C26H29NO2

Exact Mass: 387.2198

Molecular Weight: 387.52

Elemental Analysis: C, 80.59; H, 7.54; N, 3.61; O, 8.26

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 weeks
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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

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
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.