NAV

Eprotirome

Identification

Generic Name
Eprotirome
DrugBank Accession Number
DB05035
Background

Eprotirome which is a compound with promising properties for treatment of obesity and dyslipidemia. Eprotirome increases the body’s energy consumption and reduces body weight and markedly reduces blood lipids and blood glucose.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 487.144
Monoisotopic: 484.947349
Chemical Formula
C18H17Br2NO5
Synonyms
  • Eprotirome
External IDs
  • KB 2115
  • KB-2115
  • KB2115
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Pharmacology

Indication

Investigated for use/treatment in hyperlipidemia, metabolic disease, and obesity.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

KB2115 is liver selectuve TR agonist that can induce pharmacological effects in the liver. It increases energy consumption, reduces body weight and also markedly reduces blood lipids and blood glucose levels at doses not affecting heart rate, bone density or TSH levels.

Mechanism of action

KB2115 works by selectively stimulating the thyroid hormone receptor which is the protein in the body that mediates the effects of thyroid hormone. KB2115 has receptor and tissue selective properties and thereby negative effects on the heart can be avoided.

TargetActionsOrganism
UThyroid hormone receptor alphaNot AvailableHumans
UThyroid hormone receptor betaNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as bromodiphenyl ethers. These are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Bromodiphenyl ethers
Alternative Parents
Diarylethers / Phenylpropanes / Anilides / Cumenes / Phenoxy compounds / Phenol ethers / N-arylamides / 1-hydroxy-2-unsubstituted benzenoids / Bromobenzenes / 1,3-dicarbonyl compounds
show 7 more
Substituents
1,3-dicarbonyl compound / 1-hydroxy-2-unsubstituted benzenoid / Anilide / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Bromobenzene / Bromodiphenyl ether / Carbonyl group / Carboxamide group
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
958AQ7B6R1
CAS number
355129-15-6
InChI Key
VPCSYAVXDAUHLT-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-({3,5-dibromo-4-[4-hydroxy-3-(propan-2-yl)phenoxy]phenyl}carbamoyl)acetic acid
SMILES
CC(C)C1=C(O)C=CC(OC2=C(Br)C=C(NC(=O)CC(O)=O)C=C2Br)=C1

References

General References
Not Available
PubChem Compound
10299876
PubChem Substance
347827705
ChemSpider
8475344
BindingDB
50385105
ChEMBL
CHEMBL2035874
ZINC
ZINC000001494227
PDBe Ligand
64L
PDB Entries
5hkb

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentHeterozygous Familial Hypercholesterolemia (HeFH)1
2CompletedPreventionPrimary Hypercholesterolemia1
2CompletedTreatmentDyslipidemia1
2CompletedTreatmentHigh Cholesterol1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00201 mg/mLALOGPS
logP3.36ALOGPS
logP5.08Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)2.21Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area95.86 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity104.92 m3·mol-1Chemaxon
Polarizability40.47 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0103900000-91741a82ce0fd9120d4f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009400000-8982fb38cc1d624e723d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00mt-2003900000-de859d6e76843eadcbe9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-0009000000-bd952d7503220ebc688d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ap3-3514900000-8a3e4edea50f5ed6226d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-f627a87977b89303c10f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.18692
predicted
DeepCCS 1.0 (2019)
[M+H]+183.62636
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.81624
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thyroid hormone receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Isoform Alpha-1: Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.Isoform Al...
Gene Name
THRA
Uniprot ID
P10827
Uniprot Name
Thyroid hormone receptor alpha
Molecular Weight
54815.055 Da
Details2. Thyroid hormone receptor beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.
Gene Name
THRB
Uniprot ID
P10828
Uniprot Name
Thyroid hormone receptor beta
Molecular Weight
52787.16 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51