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MedKoo Cat#: 574221 | Name: Raloxifene 6-glucuronide
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Description:

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

Raloxifene 6-glucuronide is a primary metabolite of Raloxifene. Unlike raloxifene, raloxifene 6-glucuronide does not inhibit the voltage-gated potassium channel Kv4.3

Chemical Structure

Raloxifene 6-glucuronide
Raloxifene 6-glucuronide
CAS#174264-50-7

Theoretical Analysis

MedKoo Cat#: 574221

Name: Raloxifene 6-glucuronide

CAS#: 174264-50-7

Chemical Formula: C34H35NO10S

Exact Mass: 649.1982

Molecular Weight: 649.71

Elemental Analysis: C, 62.85; H, 5.43; N, 2.16; O, 24.62; S, 4.93

Price and Availability

Size Price Availability Quantity
1mg USD 675.00
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Related CAS #
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Synonym
Ral-6-Gluc, Raloxifene 6-glucuronide
IUPAC/Chemical Name
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((2-(4-hydroxyphenyl)-3-(4-(2-(piperidin-1-yl)ethoxy)benzoyl)benzo[b]thiophen-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
InChi Key
MZPMSLSINDGEPM-WKRHDJAJSA-N
InChi Code
InChI=1S/C34H35NO10S/c36-21-8-4-20(5-9-21)32-26(27(37)19-6-10-22(11-7-19)43-17-16-35-14-2-1-3-15-35)24-13-12-23(18-25(24)46-32)44-34-30(40)28(38)29(39)31(45-34)33(41)42/h4-13,18,28-31,34,36,38-40H,1-3,14-17H2,(H,41,42)/t28-,29-,30+,31-,34+/m0/s1
SMILES Code
OC(C=C1)=CC=C1C2=C(C(C3=CC=C(OCCN4CCCCC4)C=C3)=O)C5=CC=C(O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O6)C=C5S2
Appearance
Solid powder
Purity
>90% (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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Raloxifene 6-glucuronide binds to estrogen receptor with an IC50 of 290 μM. Raloxifene activates TGFβ3 promoter as a full agonist at nanomolar concentrations, and inhibits the estrogen response element-containing vitellogenin promoter expression.
In vitro activity:
The combined treatment of raloxifene and gefitinib decreased the ability of neovascularization as assessed by tube formation of endothelial cells. These results suggested the potential of the combination of raloxifene and gefitinib for the prevention of triple-negative breast cancer growth and the appearance of metastatic events. Reference: Med Oncol. 2022 Dec 9;40(1):45. https://pubmed.ncbi.nlm.nih.gov/36494506/
In vivo activity:
This study suggested that raloxifene metabolism in the duodenum was significantly slower at young age in rats, which increased the oral bioavailability of raloxifene. Raloxifene's dose at different ages should be carefully considered. Reference: Pharm Res. 2021 Aug;38(8):1357-1367. https://pubmed.ncbi.nlm.nih.gov/34322833/
Solvent mg/mL mM
Solubility
DMSO 6.5 10.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 649.71 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:
1. Du T, Sun R, Li L, Ebuzoeme C, Bui D, Zheng Z, Yin T, Liang D, Hu M, Gao S. Development and validation of ultra-high-performance liquid chromatography-mass spectrometry method for the determination of raloxifene and its phase II metabolites in plasma: Application to pharmacokinetic studies in rats. J Sep Sci. 2020 Dec;43(24):4414-4423. doi: 10.1002/jssc.202000835. Epub 2020 Nov 20. PMID: 33119204; PMCID: PMC8452178. 2. Taurin S, Rosengren RJ. Raloxifene potentiates the effect of gefitinib in triple-negative breast cancer cell lines. Med Oncol. 2022 Dec 9;40(1):45. doi: 10.1007/s12032-022-01909-3. PMID: 36494506. 3. Du T, Sun R, Etim I, Zheng Z, Liang D, Hu M, Gao S. Age-and Region-Dependent Disposition of Raloxifene in Rats. Pharm Res. 2021 Aug;38(8):1357-1367. doi: 10.1007/s11095-021-03084-y. Epub 2021 Jul 28. PMID: 34322833; PMCID: PMC8452384. 4. Kosaka K, Watanabe T, Susukida T, Aoki S, Sekine S, Kume T, Ito K. Key determinants of the circulatory exposure of organic anions: differences in hepatic uptake between multidrug resistance-associated protein 2 (Mrp2)-deficient rats and wild-type rats. Xenobiotica. 2015;45(6):556-62. doi: 10.3109/00498254.2014.997820. Epub 2014 Dec 24. PMID: 25539456.
In vitro protocol:
1. Du T, Sun R, Li L, Ebuzoeme C, Bui D, Zheng Z, Yin T, Liang D, Hu M, Gao S. Development and validation of ultra-high-performance liquid chromatography-mass spectrometry method for the determination of raloxifene and its phase II metabolites in plasma: Application to pharmacokinetic studies in rats. J Sep Sci. 2020 Dec;43(24):4414-4423. doi: 10.1002/jssc.202000835. Epub 2020 Nov 20. PMID: 33119204; PMCID: PMC8452178. 2. Taurin S, Rosengren RJ. Raloxifene potentiates the effect of gefitinib in triple-negative breast cancer cell lines. Med Oncol. 2022 Dec 9;40(1):45. doi: 10.1007/s12032-022-01909-3. PMID: 36494506.
In vivo protocol:
1. Du T, Sun R, Etim I, Zheng Z, Liang D, Hu M, Gao S. Age-and Region-Dependent Disposition of Raloxifene in Rats. Pharm Res. 2021 Aug;38(8):1357-1367. doi: 10.1007/s11095-021-03084-y. Epub 2021 Jul 28. PMID: 34322833; PMCID: PMC8452384. 2. Kosaka K, Watanabe T, Susukida T, Aoki S, Sekine S, Kume T, Ito K. Key determinants of the circulatory exposure of organic anions: differences in hepatic uptake between multidrug resistance-associated protein 2 (Mrp2)-deficient rats and wild-type rats. Xenobiotica. 2015;45(6):556-62. doi: 10.3109/00498254.2014.997820. Epub 2014 Dec 24. PMID: 25539456.
1: Clarke JD, Judson SM, Tian DD, Kirby TO, Tanna RS, Matula-Péntek A, Horváth M, Layton ME, White JR, Cech NB, Thummel KE, McCune JS, Shen DD, Paine MF. Co- consuming green tea with raloxifene decreases raloxifene systemic exposure in healthy adult participants. Clin Transl Sci. 2023 Oct;16(10):1779-1790. doi: 10.1111/cts.13578. Epub 2023 Aug 28. PMID: 37639334; PMCID: PMC10582660. 2: Du T, Sun R, Etim I, Zheng Z, Liang D, Hu M, Gao S. Age-and Region-Dependent Disposition of Raloxifene in Rats. Pharm Res. 2021 Aug;38(8):1357-1367. doi: 10.1007/s11095-021-03084-y. Epub 2021 Jul 28. PMID: 34322833; PMCID: PMC8452384. 3: Du T, Sun R, Li L, Ebuzoeme C, Bui D, Zheng Z, Yin T, Liang D, Hu M, Gao S. Development and validation of ultra-high-performance liquid chromatography-mass spectrometry method for the determination of raloxifene and its phase II metabolites in plasma: Application to pharmacokinetic studies in rats. J Sep Sci. 2020 Dec;43(24):4414-4423. doi: 10.1002/jssc.202000835. Epub 2020 Nov 20. PMID: 33119204; PMCID: PMC8452178. 4: Kosaka K, Watanabe T, Susukida T, Aoki S, Sekine S, Kume T, Ito K. Key determinants of the circulatory exposure of organic anions: differences in hepatic uptake between multidrug resistance-associated protein 2 (Mrp2)-deficient rats and wild-type rats. Xenobiotica. 2015;45(6):556-62. doi: 10.3109/00498254.2014.997820. Epub 2014 Dec 24. PMID: 25539456. 5: Chae YJ, Kim DH, Lee HJ, Sung KW, Kwon OJ, Hahn SJ. Raloxifene inhibits cloned Kv4.3 channels in an estrogen receptor-independent manner. Pflugers Arch. 2015 Aug;467(8):1663-76. doi: 10.1007/s00424-014-1602-3. Epub 2014 Sep 18. PMID: 25231973. 6: Matsuda Y, Konno Y, Hashimoto T, Nagai M, Taguchi T, Satsukawa M, Yamashita S. Quantitative assessment of intestinal first-pass metabolism of oral drugs using portal-vein cannulated rats. Pharm Res. 2015 Feb;32(2):604-16. doi: 10.1007/s11095-014-1489-x. Epub 2014 Aug 28. PMID: 25163980. 7: Dluzen DF, Sun D, Salzberg AC, Jones N, Bushey RT, Robertson GP, Lazarus P. Regulation of UDP-glucuronosyltransferase 1A1 expression and activity by microRNA 491-3p. J Pharmacol Exp Ther. 2014 Mar;348(3):465-77. doi: 10.1124/jpet.113.210658. Epub 2014 Jan 7. PMID: 24399855; PMCID: PMC3935146. 8: Sun D, Jones NR, Manni A, Lazarus P. Characterization of raloxifene glucuronidation: potential role of UGT1A8 genotype on raloxifene metabolism in vivo. Cancer Prev Res (Phila). 2013 Jul;6(7):719-30. doi: 10.1158/1940-6207.CAPR-12-0448. Epub 2013 May 16. PMID: 23682072; PMCID: PMC4057281. 9: Chang JH, Yoo P, Lee T, Klopf W, Takao D. The role of pH in the glucuronidation of raloxifene, mycophenolic acid and ezetimibe. Mol Pharm. 2009 Jul-Aug;6(4):1216-27. doi: 10.1021/mp900065b. PMID: 19449843. 10: Trontelj J, Bogataj M, Marc J, Mrhar A. Development and validation of a liquid chromatography-tandem mass spectrometry assay for determination of raloxifene and its metabolites in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Aug 15;855(2):220-7. doi: 10.1016/j.jchromb.2007.05.004. Epub 2007 May 16. PMID: 17537683.

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