Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H9I3O4 |
Molecular Weight | 621.9328 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc(c(cc1Oc2c(cc(cc2I)CC(=O)O)I)I)O
InChI
InChIKey=UOWZUVNAGUAEQC-UHFFFAOYSA-N
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)
DescriptionCurator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23776891
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23776891
Tiratricol (also known as TRIAC or triiodothyroacetic acid) is a thyroid hormone analogue, which has been studied since the 1950s. Tiratricol is used as a dietary supplement for thyroid problems including thyroid cancer. It is also used for increasing metabolic rate for weight loss, and reducing cellulite. In the US, the Food and Drug Administration (FDA) has determined that the product Triax (TRIAC, tiratricol) is not a dietary supplement but an unapproved new drug containing a powerful thyroid hormone, which may cause serious health consequences. The State of Missouri embargoed the product at its distributor (Syntrax) and the Utah-based manufacturer (Pharmatech) has agreed to stop distributing any product containing the ingredient TRIAC. The FDA has issued recalls for other tiratricol-containing products, including Tricana Metabolic Hormone Analogue, Tria-Cutz Thyroid Stimulator Dietary Supplement Capsules, and Sci-Fi-Tri-Cuts Dietary Supplement Capsules. Tiratricol is a prescription drug in France used for therapy of thyroid hormone resistance and therapy of thyroid cancer.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1860 |
0.14 nM [IC50] | ||
Target ID: CHEMBL1947 |
0.048 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | TEATROIS Approved UseTiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer. |
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Primary | TEATROIS Approved UseTiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer. |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Adverse effect of 3,5,3 triiodothyroacetic acid in the treatment of obesity]. | 2001 Jun |
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In vitro effect of Triac on resistance to thyroid hormone receptor mutants: potential basis for therapy. | 2001 Mar 28 |
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Dose-response effects of tri-iodothyroacetic acid (Triac) and other thyroid hormone analogues on glucocorticoid-induced skin atrophy in the haired mouse. | 2002 |
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Symptomatic hyperthyroidism in a patient taking the dietary supplement tiratricol. | 2002 Jun |
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Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs. | 2002 May |
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Inhibition of in vitro macrophage-induced low density lipoprotein oxidation by thyroid compounds. | 2003 Apr |
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Two resistance to thyroid hormone mutants with impaired hormone binding. | 2003 Apr |
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[Dieting preparations caused difficult-to-interpret thyroid gland disorders. Warning for "Eat&Lose"]. | 2003 Apr 24 |
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[Dieting with (un)known hormones]. | 2003 Apr 24 |
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Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. | 2003 Oct 10 |
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T3 and Triac inhibit leptin secretion and expression in brown and white rat adipocytes. | 2004 Jun 1 |
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Pentane-1,5-diol as a percutaneous absorption enhancer. | 2005 Dec |
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T-Screen as a tool to identify thyroid hormone receptor active compounds. | 2005 Feb |
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Endocrine and neuropsychological assessment in a child with a novel mutation of thyroid hormone receptor: response to 12-month triiodothyroacetic acid (TRIAC) therapy. | 2005 Jul-Aug |
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Thermogenic effect of triiodothyroacetic acid at low doses in rat adipose tissue without adverse side effects in the thyroid axis. | 2008 Apr |
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Tiratricol neutralizes bacterial endotoxins and reduces lipopolysaccharide-induced TNF-alpha production in the cell. | 2008 Oct |
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Iodothyronamines are oxidatively deaminated to iodothyroacetic acids in vivo. | 2009 Jan 26 |
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C-fin: a cultured frog tadpole tail fin biopsy approach for detection of thyroid hormone-disrupting chemicals. | 2010 Feb |
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Inhibitors of androgen receptor activation function-2 (AF2) site identified through virtual screening. | 2011 Sep 22 |
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Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6619530
3 mg/day for 3 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8140938
In fetal rat long bone cultures, 10(-7)-10(-10) M of Tiratricol and
T3, stimulated 45Ca release in a dose-dependent manner. The maximal effects were observed at 10(-7) M for both Tiratricol and T3, and were more pronounced at 5 days.
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WHO-VATC |
QD11AX08
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FDA ORPHAN DRUG |
137200
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FDA ORPHAN DRUG |
666618
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WHO-ATC |
D11AX08
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WHO-ATC |
H03AA04
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WHO-VATC |
QH03AA04
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NCI_THESAURUS |
C1553
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EU-Orphan Drug |
EU/3/17/1945
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FDA ORPHAN DRUG |
46890
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29OQ9EU4R1
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DB03604
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5803
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C010642
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CHEMBL41632
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13982
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C66605
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TIRATRICOL
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M10888
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4368
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)