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Record Information
Version2.0
Creation Date2014-10-14 21:19:35 UTC
Update Date2014-12-24 20:27:01 UTC
Accession NumberT3D4983
Identification
Common NameTiratricol
ClassSmall Molecule
DescriptionTiratricol (also known as TRIAC or triiodothyroacetic acid) is a thyroid hormone analogue. It is indicated in the management of thyroid hormone resistance syndrome and is used, in combination with levothyroxine, to suppress thyroid-stimulating hormone production in patients with thyroid cancer. It has been investigated for use in reducing goiter. It has also shown some effectiveness in reducing the atrophy caused when using corticosteroids. Tiratricol has also been widely marketed, under various trade names, as a weight loss aid. In 1999 and 2000, the United States Food and Drug Administration and Health Canada both issued warnings to the public regarding the use of dietary supplements containing tiratricol. Tiratricol is not approved for sale in Canada or the United States. It was once an approved drug in Brazil, but its marketing authorization was suspended in 2003, effectively prohibiting its sale. (Wikipedia)
Compound Type
  • Industrial/Workplace Toxin
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
3,5,39-triiodothyroacetic acid
Tiracana
TRIAC
Triiodothyroacetic acid
[4-(4-Hydroxy-3-Iodo-Phenoxy)-3,5-Diiodo-Phenyl]-Acetic Acid
Chemical FormulaC14H9I3O4
Average Molecular Mass621.932 g/mol
Monoisotopic Mass621.763 g/mol
CAS Registry Number51-24-1
IUPAC Name2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
Traditional Nametriac
SMILESOC(=O)CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1
InChI IdentifierInChI=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)
InChI KeyInChIKey=UOWZUVNAGUAEQC-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Diaryl ether
  • Phenoxy compound
  • 2-halophenol
  • 2-iodophenol
  • Phenol ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organoiodide
  • Organohalogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.67 m³·mol⁻¹ChemAxon
Polarizability40.54 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000009000-faf2d387cb07037e1ea8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0000019000-73143b34cfb6772db79cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-1359220000-af32445877396145eaf4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0000049000-9eb0f1e0124f4cae1f4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-0000279000-8449c1025cf98e1bca75JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-106v-1135912000-88d84a79f0681e18cb48JSpectraViewer
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityTiratricol is a naturally occurring metabolite of T4 (thyroxine) and a structural analog of T3 (triiodothyronine). Low concentrations of tiratricol are found in plasma, but tiratricol has no known role in thyroid physiology. Tiratricol has a high affinity for T3 receptors and suppresses thyroid stimulating hormone (TSH) secretion at therapeutic doses without causing significant peripheral effects, such as increased basal metabolism rate and heart rate. Tiratricol might lower total and LDL cholesterol, and stimulate bone formation. About 67% of an oral dose of tiratricol is absorbed; the half-life is 6 hours. (3) Serum sex hormone-binding globulin levels increased 55 +/- 13% with tiratricol, indicating an augmented hepatic response to tiratricol. Tiratricol had effected the cardiovascular function. Tiratricol has distinct augmented hepatic and skeletal thyromimetic actions of potential therapeutic value. (1)
MetabolismTiratricol is a metabolite of T4.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesTiratricol is indicated in the management of thyroid hormone resistance syndrome and is used, in combination with levothyroxine, to suppress thyroid-stimulating hormone production in patients with thyroid cancer. It has been investigated for use in reducing goiter. It has also shown some effectiveness in reducing the atrophy caused when using corticosteroids. Tiratricol has also been widely marketed, under various trade names, as a weight loss aid. In 1999 and 2000, the United States Food and Drug Administration and Health Canada both issued warnings to the public regarding the use of dietary supplements containing tiratricol. (Wikipedia)
Minimum Risk LevelNot Available
Health EffectsOrally, tiratricol can cause severe diarrhea, fatigue, lethargy, and profound weight loss. Heart attacks and strokes are possible, as well as symptoms of hyperthyroidism, including increased appetite, abdominal cramps, tremors, menstrual irregularities, nervousness, insomnia, sweating, intolerance to heat, fever, palpitations, tachycardia, increased pulse and blood pressure, chest pain, and cardiac arrhythmias. Case reports have implicated tiratricol in centrally-mediated hypothyroidism, pseudohypothyroidism, internuclear ophthalmoplegia, and hepatotoxicity. (3) It has been investigated for use in reducing goiter. It has also shown some effectiveness in reducing the atrophy caused when using corticosteroids. (Wikipedia) Tiratricol has been used to suppress pituitary TSH secretion, with reported attenuation of extrapituitary thyromimetic effects. (2)
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03604
HMDB IDNot Available
PubChem Compound ID5803
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Sherman SI, Ringel MD, Smith MJ, Kopelen HA, Zoghbi WA, Ladenson PW: Augmented hepatic and skeletal thyromimetic effects of tiratricol in comparison with levothyroxine. J Clin Endocrinol Metab. 1997 Jul;82(7):2153-8. [9215287 ]
  2. Sherman SI, Ladenson PW: Organ-specific effects of tiratricol: a thyroid hormone analog with hepatic, not pituitary, superagonist effects. J Clin Endocrinol Metab. 1992 Sep;75(3):901-5. [1517383 ]
  3. Natural Medicines - TIRATRICOL [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
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. [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. [17016423 ]