EPROTIROME

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22784847 | https://www.ncbi.nlm.nih.gov/pubmed/18160532 | https://www.ncbi.nlm.nih.gov/pubmed/24731671 | http://adisinsight.springer.com/drugs/800022362

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 Target	Pharmacology	Condition	Potency
Thyroid hormone receptor beta-1 25 Target ID: CHEMBL1947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22542282/	Agonist 2678		0.43 nM [Ki]
Thyroid hormone receptor alpha 14 Target ID: CHEMBL1860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22542282/	Agonist 2678		9.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dyslipidemia 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18160532 https://www.ncbi.nlm.nih.gov/pubmed/20220185 https://www.ncbi.nlm.nih.gov/pubmed/24731671	Primary		Phase III 656	Unknown Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Vendor/Aggregator	ID	URL
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
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
eMolecules	24462907	https://orderbb.emolecules.com/search/#?query=24462907

PubMed

Title	Date	PubMed
Selective thyromimetics for atherosclerosis and dyslipidaemia: another old target making progress.	2008 May	18447589
[Thyroid hormone analogs: an important biological supply and new therapeutic possibilities].	2008 Sep	18954857
Hotline sessions presented at the American College of Cardiology Congress 2009.	2009 Jun	19430713
The resurgence of thyromimetics as lipid-modifying agents.	2009 Sep	19705333
Lipoprotein(a) as a cardiovascular risk factor: current status.	2010 Dec	20965889
Lipid lowering with thyroid hormone and thyromimetics.	2010 Dec	20935564
Lipids: Eprotirome shows promise as a novel way to target dyslipidemia.	2010 Jul	20583340
Use of the thyroid hormone analogue eprotirome in statin-treated dyslipidemia.	2010 Mar 11	20220185
Triglyceride-mediated pathways and coronary disease: collaborative analysis of 101 studies.	2010 May 8	20452521
Thyroid hormone receptor and lipid regulation.	2010 Oct	20872316
Thyroid hormones, mitochondrial bioenergetics and lipid handling.	2010 Oct	20625286
Recent advances in preventing cardiovascular disorders by managing lipid levels.	2010 Sep 8	21173859

Patents

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 `Fri Dec 15 15:25:42 UTC 2023` Edited by `admin` on `Fri Dec 15 15:25:42 UTC 2023`
Record UNII	958AQ7B6R1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPROTIROME

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