Eprotirome

Identification

Name
Eprotirome
Accession Number
DB05035
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
KB2115
Categories
UNII
958AQ7B6R1
CAS number
Not Available
Weight
Average: 487.144
Monoisotopic: 484.947349
Chemical Formula
C18H17Br2NO5
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=CC(OC2=C(Br)C=C(NC(=O)CC(O)=O)C=C2Br)=CC=C1O

Pharmacology

Indication

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

Structured Indications
Not Available
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 AvailableHuman
UThyroid hormone receptor betaNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
10299876
PubChem Substance
347827705
ChemSpider
8475344
BindingDB
50385105
ChEMBL
CHEMBL2035874
HET
64L
PDB Entries
5hkb

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedPreventionHypercholesterolemia, Familial1
2CompletedTreatmentDyslipidemias1
2CompletedTreatmentHigh Blood Cholesterol Level1
3TerminatedTreatmentHeterozygous Familial Hypercholesterolemia1

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
Polarizability40.44 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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Bromodiphenyl ether / Diaryl ether / Cumene / Phenylpropane / Anilide / Phenoxy compound / Phenol ether / N-arylamide / Halobenzene / 1-hydroxy-2-unsubstituted benzenoid
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on October 21, 2007 16:23 / Updated on December 01, 2017 15:34