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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 of TIRATRICOL

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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 0.14 nM [IC50]
Agonist
2678
 0.048 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
TEATROIS

Approved Use

Tiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer.
Primary
Approved
8429
TEATROIS

Approved Use

Tiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer.
Primary
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Differences between the effects of thyroxine and tetraiodothyroacetic acid on TSH suppression and cardiac hypertrophy.
2001 Feb
Effects of thyroid hormones on cardiac structure: a tissue characterization study in patients with thyroid disorders before and after treatment.
2001 Jul
In vitro free radical scavenging capacity of thyroid hormones and structural analogues.
2001 Jul
[Adverse effect of 3,5,3 triiodothyroacetic acid in the treatment of obesity].
2001 Jun
Hormone selectivity in thyroid hormone receptors.
2001 Mar
In vitro effect of Triac on resistance to thyroid hormone receptor mutants: potential basis for therapy.
2001 Mar 28
Dose-response effects of tri-iodothyroacetic acid (Triac) and other thyroid hormone analogues on glucocorticoid-induced skin atrophy in the haired mouse.
2002
Symptomatic hyperthyroidism in a patient taking the dietary supplement tiratricol.
2002 Jun
Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs.
2002 May
Inhibition of in vitro macrophage-induced low density lipoprotein oxidation by thyroid compounds.
2003 Apr
Two resistance to thyroid hormone mutants with impaired hormone binding.
2003 Apr
[Dieting preparations caused difficult-to-interpret thyroid gland disorders. Warning for "Eat&Lose"].
2003 Apr 24
[Dieting with (un)known hormones].
2003 Apr 24
A report of hypothyroidism induced by an over-the-counter fat loss supplement (Tiratricol).
2003 Mar
Comparative efficacy and side effects of the treatment of euthyroid goiter with levo-thyroxine or triiodothyroacetic acid.
2003 Nov
Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.
2003 Oct 10
Potent thermogenic action of triiodothyroacetic acid in brown adipocytes.
2003 Sep
Ephedrine and tiratricol: freshly prepared mixtures forbidden in France.
2004 Apr
Inefficacy of topical thyroid hormone analogue TriAc in plaque psoriasis: results of a double-blind placebo-controlled trial.
2004 Aug
Thyroid hormone (T3) and its acetic derivative (TA3) protect low-density lipoproteins from oxidation by different mechanisms.
2004 Jun
T3 and Triac inhibit leptin secretion and expression in brown and white rat adipocytes.
2004 Jun 1
A thyroid hormone analogue, triiodothyroacetic acid, corrects corticosteroid-downregulated collagen synthesis.
2004 May
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
A patient with low free T4 and low thyroid-stimulating hormone without hypopituitarism.
2004 Oct
Pentane-1,5-diol as a percutaneous absorption enhancer.
2005 Dec
T-Screen as a tool to identify thyroid hormone receptor active compounds.
2005 Feb
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
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
A new bioluminescent cellular assay to measure the transcriptional effects of chemicals that modulate the alpha-1 thyroid hormone receptor.
2007 Sep
E449X mutation in the thyroid hormone receptor beta associated with autoimmune thyroid disease and severe neuropsychomotor involvement.
2008 Nov
Iodothyronamines are oxidatively deaminated to iodothyroacetic acids in vivo.
2009 Jan 26
Protective effect of 3,5,3'-triiodothyroacetic and 3,5,3',5'-tetraiodothyroacetic acids on serum albumin fibrillation.
2009 Sep
Active metabolism of thyroid hormone during metamorphosis of amphioxus.
2010 Jul
Non-genomic effects of thyroid hormone in adult cardiac myocytes: relevance to gene expression and cell growth.
2010 Jul
Inhibitors of androgen receptor activation function-2 (AF2) site identified through virtual screening.
2011 Sep 22
Patents

Patents

JPS5857716A
2
JPS61204526A
2

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
INN   MART.   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
FDA ORPHAN DRUG 137200
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
FDA ORPHAN DRUG 666618
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
FDA ORPHAN DRUG 862421
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
WHO-ATC D11AX08
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
WHO-ATC H03AA04
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
WHO-VATC QH03AA04
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
NCI_THESAURUS C1553
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
EU-Orphan Drug EU/3/17/1945
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
FDA ORPHAN DRUG 46890
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
Code System Code Type Description
FDA UNII
29OQ9EU4R1
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
DRUG BANK
DB03604
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-086-1
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
PUBCHEM
5803
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
MESH
C010642
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL41632
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
EVMPD
SUB11116MIG
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045232
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
SMS_ID
100000077266
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
DRUG CENTRAL
3611
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
RXCUI
13982
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C66605
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
WIKIPEDIA
TIRATRICOL
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
MERCK INDEX
m10888
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY Merck Index
CAS
51-24-1
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
INN
4368
Created by admin on Fri Dec 15 15:09:24 GMT 2023 , Edited by admin on Fri Dec 15 15:09:24 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of TIRATRICOL
SALT/SOLVATE (PARENT)
Structure of TIRATRICOL SODIUM
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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