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Details

Stereochemistry ACHIRAL
Molecular Formula C14H9I3O4
Molecular Weight 621.9328
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIRATRICOL

SMILES

c1cc(c(cc1Oc2c(cc(cc2I)CC(=O)O)I)I)O

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
81255
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2451
 0.14 nM [IC50]
Agonist
2451
 0.048 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
7968
TEATROIS

Approved Use

Tiratricol is indicated for the therapy of thyroid hormone resistance and therapy of thyroid cancer.
Primary
Approved
7968
TEATROIS

Approved Use

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

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Adverse effect of 3,5,3 triiodothyroacetic acid in the treatment of obesity].
2001 Jun
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
Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.
2003 Oct 10
T3 and Triac inhibit leptin secretion and expression in brown and white rat adipocytes.
2004 Jun 1
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
Thermogenic effect of triiodothyroacetic acid at low doses in rat adipose tissue without adverse side effects in the thyroid axis.
2008 Apr
Tiratricol neutralizes bacterial endotoxins and reduces lipopolysaccharide-induced TNF-alpha production in the cell.
2008 Oct
Iodothyronamines are oxidatively deaminated to iodothyroacetic acids in vivo.
2009 Jan 26
C-fin: a cultured frog tadpole tail fin biopsy approach for detection of thyroid hormone-disrupting chemicals.
2010 Feb
Inhibitors of androgen receptor activation function-2 (AF2) site identified through virtual screening.
2011 Sep 22
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
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]
Common Name English
T3-ACETIC ACID [USP]
Common Name English
TRIIODOTHYROACETIC ACID
Common Name English
3,3',5-TRIIODOTHYROACETIC ACID
Systematic Name English
TIRATRICOL [MI]
Common Name English
LIOTHYRONINE SODIUM IMPURITY C [EP]
Common Name English
TRIIODOTHYROACETIC ACID [USP]
Common Name English
TIRACANA
Brand Name English
T3-ACETIC ACID
Common Name English
NSC-759294
Code English
3,5,3'-TRIIODOTHYROACETATE
Common Name English
TIRATRICOL [WHO-DD]
Common Name English
LEVOTHYROXINE SODIUM IMPURITY, TRIIODOTHYROACETIC ACID, OR T3-ACETIC ACID-[USP]
Common Name English
BENZENEACETIC ACID, 4-(4-HYDROXY-3-IODOPHENOXY)-3,5-DIIODO-
Systematic 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 Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
FDA ORPHAN DRUG 137200
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
FDA ORPHAN DRUG 666618
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
WHO-ATC D11AX08
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
WHO-ATC H03AA04
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
WHO-VATC QH03AA04
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
NCI_THESAURUS C1553
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
EU-Orphan Drug EU/3/17/1945
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
FDA ORPHAN DRUG 46890
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
Code System Code Type Description
FDA UNII
29OQ9EU4R1
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
DRUG BANK
DB03604
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-086-1
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
PUBCHEM
5803
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
MESH
C010642
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL41632
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
EVMPD
SUB11116MIG
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
EPA CompTox
51-24-1
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
DRUG CENTRAL
3611
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
RXCUI
13982
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C66605
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
WIKIPEDIA
TIRATRICOL
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
MERCK INDEX
M10888
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY Merck Index
CAS
51-24-1
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
INN
4368
Created by admin on Fri Jun 25 21:55:20 UTC 2021 , Edited by admin on Fri Jun 25 21:55:20 UTC 2021
PRIMARY
ACTIVE MOIETY
Structure of TIRATRICOL
SALT/SOLVATE (PARENT)
Structure of TIRATRICOL SODIUM
NIH
NCATS
PRIVACY ACT
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