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
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)
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 |
---|---|---|---|
Target ID: CHEMBL1947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22542282/ |
0.43 nM [Ki] | ||
Target ID: CHEMBL1860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22542282/ |
9.6 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
T1/2
Value | Dose | Co-administered | Analyte | Population |
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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 |
PubMed
Title | Date | PubMed |
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[Thyroid hormone analogs: an important biological supply and new therapeutic possibilities]. | 2008 Sep |
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Lipoprotein(a) as a cardiovascular risk factor: current status. | 2010 Dec |
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Lipid lowering with thyroid hormone and thyromimetics. | 2010 Dec |
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Thyroid hormone receptor and lipid regulation. | 2010 Oct |
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Recent advances in preventing cardiovascular disorders by managing lipid levels. | 2010 Sep 8 |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29703
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ACTIVE MOIETY