182507-22-8

182507-22-8 structure

Name: Raloxifene 4'-glucuronide
Chemical Name: Raloxifene 4'-Glucuronide
CAS Number: 182507-22-8
Molecular Formula: C₃₄H₃₅NO₁₀S
Molecular Weight: 649.70700
Catalog: Research Areas Endocrinology
Create Date: 2016-07-14 04:32:52
Modify Date: 2024-01-02 22:13:07
Raloxifene 4'-glucuronide is a primary metabolite of Raloxifene. Raloxifene 4'-glucuronide formation is mediated mostly by UGT1A10 and UGT1A8. Raloxifene 4'-glucuronide binds to estrogen receptor with an IC50 of 370 μM. [1][2]. Raloxifene is a selective estrogen receptor modulator. Raloxifene activates TGFβ3 promoter as a full agonist at nanomolar concentrations, and inhibits the estrogen response element-containing vitellogenin promoter expression[3].

Name	Raloxifene 4'-Glucuronide
Synonyms	raloxifene-4-glucuronide

Description	Raloxifene 4'-glucuronide is a primary metabolite of Raloxifene. Raloxifene 4'-glucuronide formation is mediated mostly by UGT1A10 and UGT1A8. Raloxifene 4'-glucuronide binds to estrogen receptor with an IC50 of 370 μM. [1][2]. Raloxifene is a selective estrogen receptor modulator. Raloxifene activates TGFβ3 promoter as a full agonist at nanomolar concentrations, and inhibits the estrogen response element-containing vitellogenin promoter expression[3].
Related Catalog	Signaling Pathways >> Others >> Estrogen Receptor/ERR Research Areas >> Endocrinology
Target	IC50: 370 μM (Estrogen receptor)[2]
In Vitro	Expressed UGT1A8 catalyzes Raloxifene 4'-glucuronide with an apparent Km of 59 μM and a Vmax of 2.0 nmol/min/mg. Based on rates of Raloxifene glucuronidation and known extrahepatic expression, UGT1A8 and 1A10 appear to be primary contributors to Raloxifene glucuronidation in human jejunum microsomes. For human liver microsomes, the variability of Raloxifene 4'-glucuronide formation is 4-fold. Treatment of expressed UGTs with alamethicin results in minor increases in enzyme activity, whereas in human intestinal microsomes, maximal increases of 9-fold for the Raloxifene 4'-glucuronide are observed. Intrinsic clearance values in intestinal microsomes are 95 μl/min/mg for the Raloxifene 4'-glucuronide[2].
References	[1]. Izgelov D, et al. The Effect of Piperine Pro-Nano Lipospheres on Direct Intestinal Phase II Metabolism: The Raloxifene Paradigm of Enhanced Oral Bioavailability. Mol Pharm. 2018 Apr 2;15(4):1548-1555. [2]. Kemp DC, et al. Characterization of raloxifene glucuronidation in vitro: contribution of intestinal metabolism to presystemic clearance. Drug Metab Dispos. 2002 Jun;30(6):694-700. [3]. Yang NN, et al. Estrogen and raloxifene stimulate transforming growth factor-beta 3 gene expression in rat bone: a potential mechanism for estrogen- or raloxifene-mediated bone maintenance. Endocrinology. 1996 May;137(5):2075-84.

Melting Point	209-213ºC
Molecular Formula	C₃₄H₃₅NO₁₀S
Molecular Weight	649.70700
Exact Mass	649.19800
PSA	194.46000
LogP	3.57850
Index of Refraction	1.682

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