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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)c1cc(ccc1O)Oc2c(cc(cc2Br)N=C(CC(=O)O)O)Br

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.43 nM [Ki]
9.6 nM [Ki]
Conditions
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
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
PubMed

PubMed

TitleDatePubMed
Selective thyromimetics for atherosclerosis and dyslipidaemia: another old target making progress.
2008 May
Lipoprotein(a) as a cardiovascular risk factor: current status.
2010 Dec
Lipid lowering with thyroid hormone and thyromimetics.
2010 Dec
Lipids: Eprotirome shows promise as a novel way to target dyslipidemia.
2010 Jul
Use of the thyroid hormone analogue eprotirome in statin-treated dyslipidemia.
2010 Mar 11
Triglyceride-mediated pathways and coronary disease: collaborative analysis of 101 studies.
2010 May 8
Thyroid hormone receptor and lipid regulation.
2010 Oct
Recent advances in preventing cardiovascular disorders by managing lipid levels.
2010 Sep 8
Patents

Sample Use Guides

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 Sat Jun 26 01:28:09 UTC 2021
Edited
by admin
on Sat Jun 26 01:28:09 UTC 2021
Record UNII
958AQ7B6R1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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 [MI]
Common 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 Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
Code System Code Type Description
PUBCHEM
10299876
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
DRUG BANK
DB05035
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
NCI_THESAURUS
C81533
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
INN
9049
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
FDA UNII
958AQ7B6R1
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
MERCK INDEX
M4962
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL2035874
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
CAS
355129-15-6
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
EPA CompTox
355129-15-6
Created by admin on Sat Jun 26 01:28:09 UTC 2021 , Edited by admin on Sat Jun 26 01:28:09 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TARGET -> AGONIST
increased expression of the hepatic LDL-receptor gene
Related Record Type Details
ACTIVE MOIETY