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MedKoo Cat#: 558441 | Name: 4-Hydroxytoremifene

Description:

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

4-Hydroxytoremifene is a selective estrogen receptor modulator toremifene active metabolite.

Chemical Structure

4-Hydroxytoremifene
4-Hydroxytoremifene
CAS#110503-62-3

Theoretical Analysis

MedKoo Cat#: 558441

Name: 4-Hydroxytoremifene

CAS#: 110503-62-3

Chemical Formula: C26H28ClNO2

Exact Mass: 421.1800

Molecular Weight: 421.96

Elemental Analysis: C, 74.01; H, 6.69; Cl, 8.40; N, 3.32; O, 7.58

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Synonym
4-Hydroxytoremifene; 4 Hydroxytoremifene; 4Hydroxytoremifene; 4-Hydroxy Toremifene; 4-Hydroxy TOR; 4OH-TOR;
IUPAC/Chemical Name
4-[(Z)-4-Chloro-1-[4-[2-(dimethylamino)ethoxy] phenyl]-2-phenylbut-1-enyl]phenol
InChi Key
OIUCUUXSMIJSEB-QPLCGJKRSA-N
InChi Code
InChI=1S/C26H28ClNO2/c1-28(2)18-19-30-24-14-10-22(11-15-24)26(21-8-12-23(29)13-9-21)25(16-17-27)20-6-4-3-5-7-20/h3-15,29H,16-19H2,1-2H3/b26-25-
SMILES Code
OC1=CC=C(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)\CCCl)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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 421.96 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: Edavana VK, Dhakal IB, Yu X, Williams S, Kadlubar S. Sulfation of 4-hydroxy toremifene: individual variability, isoform specificity, and contribution to toremifene pharmacogenomics. Drug Metab Dispos. 2012 Jun;40(6):1210-5. doi: 10.1124/dmd.111.044040. Epub 2012 Mar 20. PubMed PMID: 22434874; PubMed Central PMCID: PMC3362788. 2: Fan PW, Zhang F, Bolton JL. 4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremifene are metabolized to unusually stable quinone methides. Chem Res Toxicol. 2000 Jan;13(1):45-52. PubMed PMID: 10649966. 3: Yao D, Zhang F, Yu L, Yang Y, van Breemen RB, Bolton JL. Synthesis and reactivity of potential toxic metabolites of tamoxifen analogues: droloxifene and toremifene o-quinones. Chem Res Toxicol. 2001 Dec;14(12):1643-53. PubMed PMID: 11743747. 4: Kangas L. Biochemical and pharmacological effects of toremifene metabolites. Cancer Chemother Pharmacol. 1990;27(1):8-12. PubMed PMID: 2147128. 5: Wiebe VJ, Benz CC, Shemano I, Cadman TB, DeGregorio MW. Pharmacokinetics of toremifene and its metabolites in patients with advanced breast cancer. Cancer Chemother Pharmacol. 1990;25(4):247-51. PubMed PMID: 2136809. 6: Kim J, Coss CC, Barrett CM, Mohler ML, Bohl CE, Li CM, He Y, Veverka KA, Dalton JT. Role and pharmacologic significance of cytochrome P-450 2D6 in oxidative metabolism of toremifene and tamoxifen. Int J Cancer. 2013 Mar 15;132(6):1475-85. doi: 10.1002/ijc.27794. Epub 2012 Sep 14. PubMed PMID: 22915089. 7: Greer AK, Dates CR, Starlard-Davenport A, Edavana VK, Bratton SM, Dhakal IB, Finel M, Kadlubar SA, Radominska-Pandya A. A potential role for human UDP-glucuronosyltransferase 1A4 promoter single nucleotide polymorphisms in the pharmacogenomics of tamoxifen and its derivatives. Drug Metab Dispos. 2014 Sep;42(9):1392-400. doi: 10.1124/dmd.114.058016. Epub 2014 Jun 10. PubMed PMID: 24917585; PubMed Central PMCID: PMC4152870. 8: Styles JA, Davies A, Davies R, White IN, Smith LL. Clastogenic and aneugenic effects of tamoxifen and some of its analogues in hepatocytes from dosed rats and in human lymphoblastoid cells transfected with human P450 cDNAs (MCL-5 cells). Carcinogenesis. 1997 Feb;18(2):303-13. PubMed PMID: 9054622. 9: Davies AM, Malone ME, White IN. Peroxidase activation of 4-hydroxytamoxifen to cause DNA damage in vitro. Biochem Soc Trans. 1995 Aug;23(3):439S. PubMed PMID: 8566328. 10: Coradini D, Biffi A, Cappelletti V, Di Fronzo G. Effects of toremifene and its main metabolites on growth of breast cancer cell lines. Anticancer Res. 1991 Nov-Dec;11(6):2191-7. PubMed PMID: 1837981. 11: Kirk J, Houlbrook S, Stuart NS, Stratford IJ, Harris AL, Carmichael J. Differential modulation of doxorubicin toxicity to multidrug and intrinsically drug resistant cell lines by anti-oestrogens and their major metabolites. Br J Cancer. 1993 Jun;67(6):1189-95. PubMed PMID: 7685615; PubMed Central PMCID: PMC1968530.