R1402

Raloxifene hydrochloride

Name: Raloxifene hydrochloride
Brand: SIGMA

selective estrogen receptor modulator (SERM), solid

Synonym(s):

Keoxifene hydrochloride, LY 156758, [6-Hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₂₈H₂₇NO₄S · HCl

CAS Number:

82640-04-8

Molecular Weight:

510.04

UNSPSC Code:

51111800

PubChem Substance ID:

24278673

NACRES:

NA.77

MDL number:

MFCD01938233

Product Name

Raloxifene hydrochloride, solid

SMILES string

Cl[H].Oc1ccc(cc1)-c2sc3cc(O)ccc3c2C(=O)c4ccc(OCCN5CCCCC5)cc4

InChI key

BKXVVCILCIUCLG-UHFFFAOYSA-N

InChI

1S/C28H27NO4S.ClH/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29;/h4-13,18,30-31H,1-3,14-17H2;1H

form

solid

color

light yellow

solubility

DMSO: soluble 28 mg/mL
H₂O: insoluble

originator

Eli Lilly

Quality Level

100

Gene Information

human ... ESR2(2100)

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Bioactive Small Molecules

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Biochem/physiol Actions

Raloxifene is benzothiophene compound and is used in treating postmenopausal osteoporosis It comparatively induces lesser risk in developing thromboembolic events and cataracts compared to tamoxifen. Raloxifene also interacts with estrogen receptors and plasma proteins.

Raloxifene is a selective estrogen receptor modulator (SERM); acts as an anti-estrogen in both breast and uterine tissue while being estrogenic in bone. May have efficacy against estrogen-sensitive cancers.

Application

Raloxifene hydrochloride has been used:

as a competitive inhibitors for estrogen receptor α in breast cancer cells
as an anti-resorptive agents to test its effect on improving bone mineral density (BMD) in six-month-old female ovariectomized rats
to test effect on viability of esophageal adenocarcinoma cells

pictograms

GHS08

signalword

Warning

hcodes

H351,H361d

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Carc. 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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The SERM/SERD bazedoxifene disrupts ESR1 helix 12 to overcome acquired hormone resistance in breast cancer cells

Fanning SW, et al.

eLife, 7, e37161-e37161 (2018)

Raloxifene

Moen MD, et al.

Drugs (2008)

Raloxifene: a selective estrogen receptor modulator (SERM) with multiple target system effects

Muchmore DB

Oncologist, 5(5), 388-392 (2000)

Ex vivo exposure to calcitonin or raloxifene improves mechanical properties of diseased bone through non-cell mediated mechanisms.

Rachel K Surowiec et al.

Bone, 173, 116805-116805 (2023-05-18)

Raloxifene (RAL) reduces clinical fracture risk despite modest effects on bone mass and density. This reduction in fracture risk may be due to improved material level-mechanical properties through a non-cell mediated increase in bone hydration. Synthetic salmon calcitonin (CAL) has

Effect of osteoporosis treatment agents on the cortical bone osteocyte microenvironment in adult estrogen-deficient, osteopenic rats

Stern AR, et al.

BoneKEy reports, 8, 115-124 (2018)

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