TIRATRICOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H9I3O4
Molecular Weight	621.9323
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1

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)

HIDE SMILES / InChI

Molecular Formula	C14H9I3O4
Molecular Weight	621.9323
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Effects of thyroid hormones on cardiac structure: a tissue characterization study in patients with thyroid disorders before and after treatment.	2001 Jul	11484889
In vitro free radical scavenging capacity of thyroid hormones and structural analogues.	2001 Jul	11431152
[Adverse effect of 3,5,3 triiodothyroacetic acid in the treatment of obesity].	2001 Jun	11510214
Hormone selectivity in thyroid hormone receptors.	2001 Mar	11222741
In vitro effect of Triac on resistance to thyroid hormone receptor mutants: potential basis for therapy.	2001 Mar 28	11306172
Dose-response effects of tri-iodothyroacetic acid (Triac) and other thyroid hormone analogues on glucocorticoid-induced skin atrophy in the haired mouse.	2002	12353707
Symptomatic hyperthyroidism in a patient taking the dietary supplement tiratricol.	2002 Jun	12059130
Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs.	2002 May	12010632
Inhibition of in vitro macrophage-induced low density lipoprotein oxidation by thyroid compounds.	2003 Apr	12697045
Two resistance to thyroid hormone mutants with impaired hormone binding.	2003 Apr	12554782
[Dieting preparations caused difficult-to-interpret thyroid gland disorders. Warning for "Eat&Lose"].	2003 Apr 24	12756693
[Dieting with (un)known hormones].	2003 Apr 24	12756691
A report of hypothyroidism induced by an over-the-counter fat loss supplement (Tiratricol).	2003 Mar	12660410
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
A thyroid hormone analogue, triiodothyroacetic acid, corrects corticosteroid-downregulated collagen synthesis.	2004 May	15186610
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
A patient with low free T4 and low thyroid-stimulating hormone without hypopituitarism.	2004 Oct	15587780
The role of transcriptional coactivator TRAP220 in myelomonocytic differentiation.	2005 Dec	16324150
Pentane-1,5-diol as a percutaneous absorption enhancer.	2005 Dec	16215760
T-Screen as a tool to identify thyroid hormone receptor active compounds.	2005 Feb	21783481
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	16218051
[Resistance to thyroid hormone].	2006 Dec	17154085
Molecular dynamics simulations of ligand dissociation from thyroid hormone receptors: evidence of the likeliest escape pathway and its implications for the design of novel ligands.	2006 Jan 12	16392786
Action of topical thyroid hormone analogues on glucocorticoid-induced skin atrophy in mice.	2006 Mar	16571090
Action of topical thyroid hormone analogue, triiodothyroacetic acid in reversing glucocorticoid-induced skin atrophy in humans.	2006 Nov	17123343
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
Inhibitors of androgen receptor activation function-2 (AF2) site identified through virtual screening.	2011 Sep 22	21846139
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:23 UTC 2023` Edited by `admin` on `Fri Dec 15 15:09:23 UTC 2023`
Record UNII	29OQ9EU4R1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIRATRICOL

Official Name

English

tiratricol [INN]

Common Name

English

LEVOTHYROXINE SODIUM IMPURITY C [EP IMPURITY]

Common Name

English

TRIIODOTHYROACETIC ACID

Common Name

English

3,3',5-TRIIODOTHYROACETIC ACID

Systematic Name

English

TIRATRICOL [MI]

Common Name

English

TIRACANA

Brand Name

English

T3-ACETIC ACID

Common Name

English

NSC-759294

Code

English

3,5,3'-TRIIODOTHYROACETATE

Common Name

English

TRIIODOTHYROACETIC ACID [USP IMPURITY]

Common Name

English

TIRATRICOL [WHO-DD]

Common Name

English

LIOTHYRONINE SODIUM IMPURITY C [EP IMPURITY]

Common Name

English

BENZENEACETIC ACID, 4-(4-HYDROXY-3-IODOPHENOXY)-3,5-DIIODO-

Systematic Name

English

LEVOTHYROXINE SODIUM IMPURITY [USP IMPURITY]

Common Name

English

T3-ACETIC ACID [USP IMPURITY]

Common Name

English

TIRATRICOL [MART.]

Common Name

English

(4-(4-HYDROXY-3-IODOPHENOXY)-3,5-DIIODOPHENYL)ACETIC ACID

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QD11AX08