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

Molecular Formula	C14H8I3O4
Molecular Weight	620.9243
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
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
Differences between the effects of thyroxine and tetraiodothyroacetic acid on TSH suppression and cardiac hypertrophy.	2001 Feb	11182751
In vitro free radical scavenging capacity of thyroid hormones and structural analogues.	2001 Jul	11431152
Hormone selectivity in thyroid hormone receptors.	2001 Mar	11222741
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
Ephedrine and tiratricol: freshly prepared mixtures forbidden in France.	2004 Apr	15148977
T3 and Triac inhibit leptin secretion and expression in brown and white rat adipocytes.	2004 Jun 1	15158754
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
[Resistance to thyroid hormone].	2006 Dec	17154085
Action of topical thyroid hormone analogue, triiodothyroacetic acid in reversing glucocorticoid-induced skin atrophy in humans.	2006 Nov	17123343
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
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 `Sat Dec 16 12:21:43 UTC 2023` Edited by `admin` on `Sat Dec 16 12:21:43 UTC 2023`
Record UNII	3HK9045D54
Record Status	`Validated (UNII)`
Record Version

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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