Tiratricol

Identification

Name
Tiratricol
Accession Number
DB03604  (EXPT00217, DB12922)
Type
Small Molecule
Groups
Investigational
Description

A metabolite of T3 and T4 thyroid hormones; promoted for hyperlipidemia, localized lipodystrophy, and obesity. Tiratricol has been used in trials studying the treatment of Allan-Herndon-Dudley Syndrome.

Structure
Thumb
Synonyms
  • 3',3,5-Triiodothyroacetic acid
  • Tiratricolum
  • Triacana
  • Triiodothyroacetic acid
Product Ingredients
IngredientUNIICASInChI Key
Tiratricol sodium3HK9045D541477-04-9BBBAIWCYEJXUMH-UHFFFAOYSA-M
Categories
UNII
29OQ9EU4R1
CAS number
51-24-1
Weight
Average: 621.9323
Monoisotopic: 621.763489036
Chemical Formula
C14H9I3O4
InChI Key
UOWZUVNAGUAEQC-UHFFFAOYSA-N
InChI
InChI=1S/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)
IUPAC Name
2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
SMILES
OC(=O)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
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
DrugInteraction
(R)-warfarinTiratricol may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinTiratricol may increase the anticoagulant activities of (S)-Warfarin.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Tiratricol.
4-hydroxycoumarinTiratricol may increase the anticoagulant activities of 4-hydroxycoumarin.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Tiratricol.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Tiratricol.
7,9-DimethylguanineThe serum concentration of 7,9-Dimethylguanine can be increased when it is combined with Tiratricol.
8-azaguanineThe serum concentration of 8-azaguanine can be increased when it is combined with Tiratricol.
8-chlorotheophyllineThe serum concentration of 8-chlorotheophylline can be increased when it is combined with Tiratricol.
9-DeazaguanineThe serum concentration of 9-Deazaguanine can be increased when it is combined with Tiratricol.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5803
PubChem Substance
46504696
ChemSpider
5598
BindingDB
18862
ChEMBL
CHEMBL41632
IUPHAR
2637
Guide to Pharmacology
GtP Drug Page
HET
4HY
Wikipedia
Tiratricol
PDB Entries
1nq0 / 1nq1 / 1nq2 / 1nuo / 2pin / 2pit / 2piu / 2pkl / 2qpy / 3d57
show 3 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Not Yet RecruitingTreatmentAllan-Herndon-Dudley Syndrome1

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 Solubility0.00539 mg/mLALOGPS
logP5.27ALOGPS
logP5.59ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.31ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.67 m3·mol-1ChemAxon
Polarizability40.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6831
Blood Brain Barrier+0.7944
Caco-2 permeable+0.628
P-glycoprotein substrateNon-substrate0.5904
P-glycoprotein inhibitor INon-inhibitor0.8432
P-glycoprotein inhibitor IINon-inhibitor0.9274
Renal organic cation transporterNon-inhibitor0.8986
CYP450 2C9 substrateNon-substrate0.7944
CYP450 2D6 substrateNon-substrate0.9201
CYP450 3A4 substrateNon-substrate0.6595
CYP450 1A2 substrateInhibitor0.7505
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.9333
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8679
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6166
Ames testNon AMES toxic0.9047
CarcinogenicityNon-carcinogens0.8759
BiodegradationNot ready biodegradable0.975
Rat acute toxicity3.8459 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.939
hERG inhibition (predictor II)Non-inhibitor0.8942
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Diphenylethers
Alternative Parents
Diarylethers / Phenoxy compounds / Phenol ethers / O-iodophenols / Iodobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl iodides / Monocarboxylic acids and derivatives / Carboxylic acids / Organoiodides
show 3 more
Substituents
Diphenylether / Diaryl ether / Phenoxy compound / 2-halophenol / 2-iodophenol / Phenol ether / Phenol / 1-hydroxy-2-unsubstituted benzenoid / Halobenzene / Iodobenzene
show 14 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
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 09:10