TIRATRICOL SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H8I3O4.Na
Molecular Weight	643.9141
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].OC1=CC=C(OC2=C(I)C=C(CC([O-])=O)C=C2I)C=C1I

InChI

InChIKey=BBBAIWCYEJXUMH-UHFFFAOYSA-M

InChI=1S/C14H9I3O4.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Description
Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-528-tiratricol
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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thyroid hormone receptor alpha 14 Target ID: CHEMBL1860 Sources: http://www.genome.jp/kegg-bin/get_htext?br08310+D07214	Agonist 2678		0.14 nM [IC50]
Thyroid hormone receptor beta-1 25 Target ID: CHEMBL1947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12699376 \| http://www.genome.jp/kegg-bin/get_htext?br08310+D07214	Agonist 2678		0.048 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Thyroid cancer 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1934526	Primary	Approved 8429	TEATROIS Approved Use Tiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer.
Rhyroid hormone resistance syndrome 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2964020 https://www.ncbi.nlm.nih.gov/pubmed/2753985 https://www.ncbi.nlm.nih.gov/pubmed/20020587	Primary	Approved 8429	TEATROIS Approved Use Tiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer.
Allan-Herndon-Dudley syndrome 2 Sources: https://clinicaltrials.gov/ct2/show/NCT02060474	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Binding of 3,5,3'-triiodothyronine (T3) and its analogs to the in vitro translational products of c-erbA protooncogenes: differences in the affinity of the alpha- and beta-forms for the acetic acid analog and failure of the human testis and kidney alpha-2 products to bind T3.	1990 Feb	2158622
Differences between the effects of thyroxine and tetraiodothyroacetic acid on TSH suppression and cardiac hypertrophy.	2001 Feb	11182751
[Dieting preparations caused difficult-to-interpret thyroid gland disorders. Warning for "Eat&Lose"].	2003 Apr 24	12756693
Comparative efficacy and side effects of the treatment of euthyroid goiter with levo-thyroxine or triiodothyroacetic acid.	2003 Nov	14602763
Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.	2003 Oct 10	12871948
Potent thermogenic action of triiodothyroacetic acid in brown adipocytes.	2003 Sep	14523556
Ephedrine and tiratricol: freshly prepared mixtures forbidden in France.	2004 Apr	15148977
Inefficacy of topical thyroid hormone analogue TriAc in plaque psoriasis: results of a double-blind placebo-controlled trial.	2004 Aug	15327560
Thyroid hormone (T3) and its acetic derivative (TA3) protect low-density lipoproteins from oxidation by different mechanisms.	2004 Jun	15283976
T3 and Triac inhibit leptin secretion and expression in brown and white rat adipocytes.	2004 Jun 1	15158754
Comparison of the effects of 3,5,3'-triiodothyroacetic Acid and triiodothyronine on goiter prevention and involution and on hepatic and skeletal parameters in rats.	2004 May	15156408
Action of topical thyroid hormone analogues on glucocorticoid-induced skin atrophy in mice.	2006 Mar	16571090
A new bioluminescent cellular assay to measure the transcriptional effects of chemicals that modulate the alpha-1 thyroid hormone receptor.	2007 Sep	17532181
Thermogenic effect of triiodothyroacetic acid at low doses in rat adipose tissue without adverse side effects in the thyroid axis.	2008 Apr	18285526
Stability indicating validated HPLC method for quantification of levothyroxine with eight degradation peaks in the presence of excipients.	2008 Aug 6	18524511
3'-monoiodothyronine sulfate and Triac sulfate are thyroid hormone metabolites in developing sheep.	2008 Feb	18091342
Thyroid dysfunction due to over-the-counter usage of tiratricol.	2008 Jul	18715309
Factitious thyrotoxicosis induced by mesotherapy: a case report.	2008 Jun	18578617
E449X mutation in the thyroid hormone receptor beta associated with autoimmune thyroid disease and severe neuropsychomotor involvement.	2008 Nov	19169471
Tiratricol neutralizes bacterial endotoxins and reduces lipopolysaccharide-induced TNF-alpha production in the cell.	2008 Oct	18844678
Iodothyronamines are oxidatively deaminated to iodothyroacetic acids in vivo.	2009 Jan 26	19105176
Protective effect of 3,5,3'-triiodothyroacetic and 3,5,3',5'-tetraiodothyroacetic acids on serum albumin fibrillation.	2009 Sep	19381627
C-fin: a cultured frog tadpole tail fin biopsy approach for detection of thyroid hormone-disrupting chemicals.	2010 Feb	20821457
Active metabolism of thyroid hormone during metamorphosis of amphioxus.	2010 Jul	21558188
Non-genomic effects of thyroid hormone in adult cardiac myocytes: relevance to gene expression and cell growth.	2010 Jul	20232113
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

Sample Use Guides

In Vivo Use Guide

3 mg/day for 3 weeks

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

TIRATRICOL SODIUM

Common Name

English

SODIUM 4-(4-HYDROXY-3-IODOPHENOXY)-3,5-DIIODOPHENYLACETATE

Systematic Name

English

Code System Code Type Description

DRUG BANK

DBSALT002405