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(I)=C(O)C=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 15 Target ID: CHEMBL1860 Sources: http://www.genome.jp/kegg-bin/get_htext?br08310+D07214	Agonist 2752		0.14 nM [IC50]
Thyroid hormone receptor beta-1 26 Target ID: CHEMBL1947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12699376 \| http://www.genome.jp/kegg-bin/get_htext?br08310+D07214	Agonist 2752		0.048 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Thyroid cancer 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1934526	Primary	Approved 8583	TEATROIS Approved Use Tiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer.
Rhyroid hormone resistance syndrome 3 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 8583	TEATROIS Approved Use Tiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer.
Allan-Herndon-Dudley syndrome 3 Sources: https://clinicaltrials.gov/ct2/show/NCT02060474	Primary	Phase II 1147	Unknown Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
5653 nM × min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2588936/	1050 μg single, oral dose: 1050 μg route of administration: Oral experiment type: SINGLE co-administered:		TIRATRICOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8690 nM × min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2588936/	1050 μg single, intravenous dose: 1050 μg route of administration: Intravenous experiment type: SINGLE co-administered:		TIRATRICOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2588936/	1050 μg single, oral dose: 1050 μg route of administration: Oral experiment type: SINGLE co-administered:		TIRATRICOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2588936/	1050 μg single, intravenous dose: 1050 μg route of administration: Intravenous experiment type: SINGLE co-administered:		TIRATRICOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3900 ug 3 times / day multiple, oral Highest studied dose Dose: 3900 ug, 3 times / day Route: oral Route: multiple Dose: 3900 ug, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8325946/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8325946/	Sources: https://pubmed.ncbi.nlm.nih.gov/8325946/
24 ug/kg 2 times / day multiple, oral Highest studied dose Dose: 24 ug/kg, 2 times / day Route: oral Route: multiple Dose: 24 ug/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9215287/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9215287/	Sources: https://pubmed.ncbi.nlm.nih.gov/9215287/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 OATP1B1 1079 CYP1A2 2153 CYP19A1 429 P-gp 1741 BCRP 910	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQxNjMyIn19	inconclusive [IC50 12.5893 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQxNjMyIn19	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDE2MzIifX0=	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDE2MzIifX0=	no [IC50 >10 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5803#section=BioAssay-Results Page: 85.0	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5803#section=BioAssay-Results Page: 3.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5803#section=BioAssay-Results Page: 247.0	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5803#section=BioAssay-Results Page: 65.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQxNjMyIn19	yes [IC50 5.0119 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/36269563/	yes [Inhibition 20 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5803#section=BioAssay-Results Page: 34.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5803#section=BioAssay-Results Page: 235 \| 240	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5803#section=BioAssay-Results Page: 185.0

PubMed

Title	Date	PubMed
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015-01-05	25455453
Inhibitors of androgen receptor activation function-2 (AF2) site identified through virtual screening.	2011-09-22	21846139
Active metabolism of thyroid hormone during metamorphosis of amphioxus.	2010-07	21558188
Non-genomic effects of thyroid hormone in adult cardiac myocytes: relevance to gene expression and cell growth.	2010-07	20232113
C-fin: a cultured frog tadpole tail fin biopsy approach for detection of thyroid hormone-disrupting chemicals.	2010-02	20821457
Protective effect of 3,5,3'-triiodothyroacetic and 3,5,3',5'-tetraiodothyroacetic acids on serum albumin fibrillation.	2009-09	19381627
Iodothyronamines are oxidatively deaminated to iodothyroacetic acids in vivo.	2009-01-26	19105176
E449X mutation in the thyroid hormone receptor beta associated with autoimmune thyroid disease and severe neuropsychomotor involvement.	2008-11	19169471
Tiratricol neutralizes bacterial endotoxins and reduces lipopolysaccharide-induced TNF-alpha production in the cell.	2008-10	18844678
Stability indicating validated HPLC method for quantification of levothyroxine with eight degradation peaks in the presence of excipients.	2008-08-06	18524511
Thyroid dysfunction due to over-the-counter usage of tiratricol.	2008-07	18715309
Factitious thyrotoxicosis induced by mesotherapy: a case report.	2008-06	18578617
Thermogenic effect of triiodothyroacetic acid at low doses in rat adipose tissue without adverse side effects in the thyroid axis.	2008-04	18285526
3'-monoiodothyronine sulfate and Triac sulfate are thyroid hormone metabolites in developing sheep.	2008-02	18091342
A new bioluminescent cellular assay to measure the transcriptional effects of chemicals that modulate the alpha-1 thyroid hormone receptor.	2007-09	17532181
[Resistance to thyroid hormone].	2006-12	17154085
Action of topical thyroid hormone analogue, triiodothyroacetic acid in reversing glucocorticoid-induced skin atrophy in humans.	2006-11	17123343
Action of topical thyroid hormone analogues on glucocorticoid-induced skin atrophy in mice.	2006-03	16571090
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.	2006-01-12	16392786
The role of transcriptional coactivator TRAP220 in myelomonocytic differentiation.	2005-12	16324150
Pentane-1,5-diol as a percutaneous absorption enhancer.	2005-12	16215760
Endocrine and neuropsychological assessment in a child with a novel mutation of thyroid hormone receptor: response to 12-month triiodothyroacetic acid (TRIAC) therapy.	2005-10-13	16218051
T-Screen as a tool to identify thyroid hormone receptor active compounds.	2005-02	21783481
A patient with low free T4 and low thyroid-stimulating hormone without hypopituitarism.	2004-10	15587780
Inefficacy of topical thyroid hormone analogue TriAc in plaque psoriasis: results of a double-blind placebo-controlled trial.	2004-08	15327560
T3 and Triac inhibit leptin secretion and expression in brown and white rat adipocytes.	2004-06-01	15158754
Thyroid hormone (T3) and its acetic derivative (TA3) protect low-density lipoproteins from oxidation by different mechanisms.	2004-06	15283976
A thyroid hormone analogue, triiodothyroacetic acid, corrects corticosteroid-downregulated collagen synthesis.	2004-05	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.	2004-05	15156408
Ephedrine and tiratricol: freshly prepared mixtures forbidden in France.	2004-04	15148977
Comparative efficacy and side effects of the treatment of euthyroid goiter with levo-thyroxine or triiodothyroacetic acid.	2003-11	14602763
Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.	2003-10-10	12871948
Potent thermogenic action of triiodothyroacetic acid in brown adipocytes.	2003-09	14523556
[Dieting preparations caused difficult-to-interpret thyroid gland disorders. Warning for "Eat&Lose"].	2003-04-24	12756693
[Dieting with (un)known hormones].	2003-04-24	12756691
Inhibition of in vitro macrophage-induced low density lipoprotein oxidation by thyroid compounds.	2003-04	12697045
Two resistance to thyroid hormone mutants with impaired hormone binding.	2003-04	12554782
A report of hypothyroidism induced by an over-the-counter fat loss supplement (Tiratricol).	2003-03	12660410
Symptomatic hyperthyroidism in a patient taking the dietary supplement tiratricol.	2002-06	12059130
Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs.	2002-05	12010632
Dose-response effects of tri-iodothyroacetic acid (Triac) and other thyroid hormone analogues on glucocorticoid-induced skin atrophy in the haired mouse.	2002	12353707
Effects of thyroid hormones on cardiac structure: a tissue characterization study in patients with thyroid disorders before and after treatment.	2001-07	11484889
In vitro free radical scavenging capacity of thyroid hormones and structural analogues.	2001-07	11431152
[Adverse effect of 3,5,3 triiodothyroacetic acid in the treatment of obesity].	2001-06	11510214
In vitro effect of Triac on resistance to thyroid hormone receptor mutants: potential basis for therapy.	2001-03-28	11306172
Hormone selectivity in thyroid hormone receptors.	2001-03	11222741
Differences between the effects of thyroxine and tetraiodothyroacetic acid on TSH suppression and cardiac hypertrophy.	2001-02	11182751
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.	1990-02	2158622

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 `Mon Mar 31 17:48:24 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:24 GMT 2025`
Record UNII	29OQ9EU4R1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIRACANA

Preferred Name

English

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

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