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Details

Stereochemistry ACHIRAL
Molecular Formula C18H17Br2NO5
Molecular Weight 487.139
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPROTIROME

SMILES

CC(C)C1=C(O)C=CC(OC2=C(Br)C=C(NC(=O)CC(O)=O)C=C2Br)=C1

InChI

InChIKey=VPCSYAVXDAUHLT-UHFFFAOYSA-N
InChI=1S/C18H17Br2NO5/c1-9(2)12-7-11(3-4-15(12)22)26-18-13(19)5-10(6-14(18)20)21-16(23)8-17(24)25/h3-7,9,22H,8H2,1-2H3,(H,21,23)(H,24,25)

HIDE SMILES / InChI

Molecular Formula C18H17Br2NO5
Molecular Weight 487.139
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Eprotirome (KB2115) is a thyroid hormone mimetic developed at Karo Bio AB (Huddinge, Sweden). Eprotirome has a 22-fold higher affinity for thyroid hormone receptor (TR)β in comparison with TRα. It lowers plasma LDL cholesterol and stimulates bile acid synthesis. Eprotirome can lower LDL cholesterol concentrations in patients with familial hypercholesterolaemia when added to conventional statin treatment with or without ezetimibe, but that it has the potential to induce liver injury. These findings, along with findings of cartilage damage in dogs, raise serious doubts about selective thyroid hormone mimetics as a therapeutic approach to lower LDL cholesterol concentrations. Eprotirome development was discontinued.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.43 nM [Ki]
9.6 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
2000 μg single, oral
EPROTIROME plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
Phase 2-3 studies for the treatment of familial hypercholesterolaemia: 25 - 100 ug daily
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
958AQ7B6R1
Record Status Validated (UNII)
Record Version