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MedKoo Cat#: 414473 | Name: Norendoxifen

Description:

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

Norendoxifen, also known as 4-hydroxy-N, N-didesmethyltamoxifen, is a nonsteroidal aromatase inhibitor of the triphenylethylene group that was never marketed. It is an active metabolite of the selective estrogen receptor modulator tamoxifen.

Chemical Structure

Norendoxifen
Norendoxifen
CAS#1308808-22-1

Theoretical Analysis

MedKoo Cat#: 414473

Name: Norendoxifen

CAS#: 1308808-22-1

Chemical Formula: C24H25NO2

Exact Mass: 359.1885

Molecular Weight: 359.47

Elemental Analysis: C, 80.19; H, 7.01; N, 3.90; O, 8.90

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Norendoxifen; Z-Norendoxifen
IUPAC/Chemical Name
4-((1Z)-1-(4-(2-Aminoethoxy)phenyl)-2-phenyl-1-buten-1-yl)phenol
InChi Key
YCQBLTPGQSYLHD-VHXPQNKSSA-N
InChi Code
InChI=1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3/b24-23-
SMILES Code
OC1=CC=C(/C(C2=CC=C(OCCN)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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 359.47 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: Ma J, Chu Z, Lu JBL, Liu J, Zhang Q, Liu Z, Tang D. The Cytochrome P450 Enzyme Responsible for the Production of (Z)-Norendoxifen in vitro. Chem Biodivers. 2018 Jan;15(1). doi: 10.1002/cbdv.201700287. Epub 2017 Dec 28. PMID: 28834279. 2: Liu J, Flockhart PJ, Lu D, Lv W, Lu WJ, Han X, Cushman M, Flockhart DA. Inhibition of cytochrome p450 enzymes by the e- and z-isomers of norendoxifen. Drug Metab Dispos. 2013 Sep;41(9):1715-20. doi: 10.1124/dmd.113.052506. Epub 2013 Jul 3. PMID: 23824607; PMCID: PMC3876808. 3: Valny M, Honsa P, Kirdajova D, Kamenik Z, Anderova M. Tamoxifen in the Mouse Brain: Implications for Fate-Mapping Studies Using the Tamoxifen-Inducible Cre- loxP System. Front Cell Neurosci. 2016 Oct 20;10:243. doi: 10.3389/fncel.2016.00243. PMID: 27812322; PMCID: PMC5071318. 4: Lu WJ, Xu C, Pei Z, Mayhoub AS, Cushman M, Flockhart DA. The tamoxifen metabolite norendoxifen is a potent and selective inhibitor of aromatase (CYP19) and a potential lead compound for novel therapeutic agents. Breast Cancer Res Treat. 2012 May;133(1):99-109. doi: 10.1007/s10549-011-1699-4. Epub 2011 Aug 4. PMID: 21814747. 5: Lv W, Liu J, Skaar TC, Flockhart DA, Cushman M. Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities. J Med Chem. 2015 Mar 26;58(6):2623-48. doi: 10.1021/jm501218e. Epub 2015 Mar 9. PMID: 25751283; PMCID: PMC4687028. 6: Lv W, Liu J, Lu D, Flockhart DA, Cushman M. Synthesis of mixed (E,Z)-, (E)-, and (Z)-norendoxifen with dual aromatase inhibitory and estrogen receptor modulatory activities. J Med Chem. 2013 Jun 13;56(11):4611-8. doi: 10.1021/jm400364h. Epub 2013 Jun 3. PMID: 23731360; PMCID: PMC4043309. 7: Lim JS, Sutiman N, Muerdter TE, Singh O, Cheung YB, Ng RC, Yap YS, Wong NS, Ang PC, Dent R, Schroth W, Schwab M, Chowbay B. Association of CYP2C19*2 and associated haplotypes with lower norendoxifen concentrations in tamoxifen- treated Asian breast cancer patients. Br J Clin Pharmacol. 2016 Jun;81(6):1142-52. doi: 10.1111/bcp.12886. Epub 2016 Mar 8. PMID: 26799162; PMCID: PMC4876188. 8: Zhao LM, Jin HS, Liu J, Skaar TC, Ipe J, Lv W, Flockhart DA, Cushman M. A new Suzuki synthesis of triphenylethylenes that inhibit aromatase and bind to estrogen receptors α and β. Bioorg Med Chem. 2016 Nov 1;24(21):5400-5409. doi: 10.1016/j.bmc.2016.08.064. Epub 2016 Aug 31. PMID: 27647367; PMCID: PMC5065788. 9: Saladores P, Mürdter T, Eccles D, Chowbay B, Zgheib NK, Winter S, Ganchev B, Eccles B, Gerty S, Tfayli A, Lim JS, Yap YS, Ng RC, Wong NS, Dent R, Habbal MZ, Schaeffeler E, Eichelbaum M, Schroth W, Schwab M, Brauch H. Tamoxifen metabolism predicts drug concentrations and outcome in premenopausal patients with early breast cancer. Pharmacogenomics J. 2015 Feb;15(1):84-94. doi: 10.1038/tpj.2014.34. Epub 2014 Aug 5. PMID: 25091503; PMCID: PMC4308646. 10: Johänning J, Kröner P, Thomas M, Zanger UM, Nörenberg A, Eichelbaum M, Schwab M, Brauch H, Schroth W, Mürdter TE. The formation of estrogen-like tamoxifen metabolites and their influence on enzyme activity and gene expression of ADME genes. Arch Toxicol. 2018 Mar;92(3):1099-1112. doi: 10.1007/s00204-017-2147-y. Epub 2017 Dec 28. PMID: 29285606; PMCID: PMC5866846.

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