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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
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 0.43 nM [Ki]
Agonist
2752
 9.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18160532
2000 μg single, oral
dose: 2000 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROTIROME plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00C1CG
https://www.1pchem.com/search?query=1P00C1CG
AK Scientific
1757AH
https://aksci.com/item_detail.php?cat=1757AH
BOC Sciences
355129-15-6
http://www.bocsci.com/description.asp?cas=355129-15-6
Cayman Chemical
10011054
http://www.caymanchem.com/app/template/Product.vm/catalog/10011054
eMolecules
24462907
https://orderbb.emolecules.com/search/#?query=24462907
MolPort
MolPort-009-019-360
https://www.molport.com/shop/molecule-link/MolPort-009-019-360
MuseChem
I006693
https://www.musechem.com/product/I006693.html
TargetMol
T5360
https://www.targetmol.com/search?keyword=T5360
Toronto Research Chemicals
E590155
https://www.trc-canada.com/product-detail/?CatNum=E590155
PubMed

PubMed

TitleDatePubMed
Lipoprotein(a) as a cardiovascular risk factor: current status.
2010-12
Lipid lowering with thyroid hormone and thyromimetics.
2010-12
Thyroid hormone receptor and lipid regulation.
2010-10
Thyroid hormones, mitochondrial bioenergetics and lipid handling.
2010-10
Recent advances in preventing cardiovascular disorders by managing lipid levels.
2010-09-08
Lipids: Eprotirome shows promise as a novel way to target dyslipidemia.
2010-07
Triglyceride-mediated pathways and coronary disease: collaborative analysis of 101 studies.
2010-05-08
Use of the thyroid hormone analogue eprotirome in statin-treated dyslipidemia.
2010-03-11
The resurgence of thyromimetics as lipid-modifying agents.
2009-09
Hotline sessions presented at the American College of Cardiology Congress 2009.
2009-06
[Thyroid hormone analogs: an important biological supply and new therapeutic possibilities].
2008-09
Selective thyromimetics for atherosclerosis and dyslipidaemia: another old target making progress.
2008-05
Patents

Patents

EP2609910A1
1
WO2014023698A1
1

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
Created
by admin
on Mon Mar 31 17:57:22 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:22 GMT 2025
Record UNII
958AQ7B6R1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPROTIROME [MI]
Preferred Name English
EPROTIROME
INN   MI   WHO-DD  
INN  
Official Name English
3-((3,5-DIBROMO-4-(4-HYDROXY-3-(PROPAN-2-YL)PHENOXY)PHENYL)AMINO)-3-OXOPROPANOIC ACID
Systematic Name English
Eprotirome [WHO-DD]
Common Name English
eprotirome [INN]
Common Name English
KB-2115
Common Name English
BMS-356384
Common Name English
KB2115
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
Code System Code Type Description
PUBCHEM
10299876
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
DRUG BANK
DB05035
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
NCI_THESAURUS
C81533
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
INN
9049
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
FDA UNII
958AQ7B6R1
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
MERCK INDEX
m4962
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL2035874
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
CAS
355129-15-6
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID00189021
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
SMS_ID
300000034180
Created by admin on Mon Mar 31 17:57:22 GMT 2025 , Edited by admin on Mon Mar 31 17:57:22 GMT 2025
PRIMARY
Related Record Type Details
SODIUM/BILE ACID COTRANSPORTER
TRANSPORTER -> SUBSTRATE
THYROID HORMONE RECEPTOR BETA
TARGET -> AGONIST
increased expression of the hepatic LDL-receptor gene
Related Record Type Details
Structure of EPROTIROME
ACTIVE MOIETY
NIH
NCATS
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