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SML1900

Sigma-Aldrich

Sobetirome

≥98% (HPLC)

Synonym(e):

2-[4-[[4-Hydroxy-3-(1-methylethyl)phenyl]methyl]-3,5-dimethylphenoxy]acetic acid, 3,5-Dimethyl-4-(4′-hydroxy-3′-isopropylbenzyl)phenoxyacetic acid, GC 1, GC-1

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About This Item

Empirische Formel (Hill-System):
C20H24O4
CAS-Nummer:
211110-63-3
Molekulargewicht:
328.40
UNSPSC-Code:
51111800
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 10 mg/mL, clear

Lagertemp.

−20°C

InChI

1S/C20H24O4/c1-12(2)17-9-15(5-6-19(17)21)10-18-13(3)7-16(8-14(18)4)24-11-20(22)23/h5-9,12,21H,10-11H2,1-4H3,(H,22,23)

InChIKey

QNAZTOHXCZPOSA-UHFFFAOYSA-N

Biochem./physiol. Wirkung

Sobetirome is also termed as 2-(4-(4-(benzyloxy)-3-isopropylbenzyl)-3,5-dimethylphenoxy)acetic acid/ GC-1. It has an inner-ring and negatively charged carboxylate groups at physiological pH. Sobetirome is considered as a cholesterol lowering agent in humans.
Sobetirome is an orally active and potent agonist at thyroid hormone receptor (TR) β and TRα that displays selective tissue action. Sobetirome is devoid of thyrotoxic adverse effects on the heart, bone, and skeletal muscle.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Analysenzertifikate (COA)

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Sobetirome prodrug esters with enhanced blood?brain barrier permeability.
Placzek AT, et al.
Bioorganic & Medicinal Chemistry, 24(22), 5842-5854 (2016)
Jan Lammel Lindemann et al.
Expert opinion on therapeutic targets, 20(2), 145-149 (2015-11-14)
Sobetirome binds selectively to the main hepatic form of thyroid hormone (TH) receptor, TRβ1, compared to TRα1, which is principally responsible for thyrotoxic effects on heart, muscle and bone. Sobetirome also preferentially accumulates in liver. It was originally envisaged that
K Kannisto et al.
Atherosclerosis, 237(2), 544-554 (2014-12-03)
Thyroid hormone reduces plasma cholesterol and increases expression of low-density lipoprotein receptor (LDL-R) in liver, an effect mediated by thyroid receptor β (TRβ). The selective TRβ modulator GC-1 also enhances several steps in reverse cholesterol transport and can decrease serum
Ester-to-amide rearrangement of ethanolamine-derived prodrugs of sobetirome with increased blood-brain barrier penetration.
Ferrara SJ, et al.
Bioorganic & Medicinal Chemistry, 25(10), 2743-2753 (2017)
Andrew T Placzek et al.
Bioorganic & medicinal chemistry, 24(22), 5842-5854 (2016-10-26)
There is currently great interest in developing drugs that stimulate myelin repair for use in demyelinating diseases such as multiple sclerosis. Thyroid hormone plays a key role in stimulating myelination during development and also controls the expression of important genes
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