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

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
Effects of thyroid hormones on cardiac structure: a tissue characterization study in patients with thyroid disorders before and after treatment.	2001 Jul	11484889
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
Two resistance to thyroid hormone mutants with impaired hormone binding.	2003 Apr	12554782
Thyroid hormone (T3) and its acetic derivative (TA3) protect low-density lipoproteins from oxidation by different mechanisms.	2004 Jun	15283976
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
C-fin: a cultured frog tadpole tail fin biopsy approach for detection of thyroid hormone-disrupting chemicals.	2010 Feb	20821457
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

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