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Tiratricol

Alias: triiodothyroacetic acid; TRIAC; Tiratricol
Cat No.:V16486 Purity: ≥97%
Tiratricol is a thyroid hormone analog that has been used to inhibit pituitary thyroid-stimulating hormone secretion and reduce the efficacy of extrapituitary thyroxine.
Tiratricol
Tiratricol Chemical Structure CAS No.: 51-24-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Tiratricol is a thyroid hormone analog that has been used to inhibit pituitary thyroid-stimulating hormone secretion and reduce the efficacy of extrapituitary thyroxine.
Biological Activity I Assay Protocols (From Reference)
ADME/Pharmacokinetics
Metabolism / Metabolites
Tiratricol is a metabolite of T4.
Toxicity/Toxicokinetics
Toxicity Summary
Tiratricol is a naturally occurring metabolite of T4 (thyroxine) and a structural analog of T3 (triiodothyronine). Low concentrations of tiratricol are found in plasma, but tiratricol has no known role in thyroid physiology. Tiratricol has a high affinity for T3 receptors and suppresses thyroid stimulating hormone (TSH) secretion at therapeutic doses without causing significant peripheral effects, such as increased basal metabolism rate and heart rate. Tiratricol might lower total and LDL cholesterol, and stimulate bone formation. About 67% of an oral dose of tiratricol is absorbed; the half-life is 6 hours. (L2139) Serum sex hormone-binding globulin levels increased 55 +/- 13% with tiratricol, indicating an augmented hepatic response to tiratricol. Tiratricol had effected the cardiovascular function. Tiratricol has distinct augmented hepatic and skeletal thyromimetic actions of potential therapeutic value. (A15458)
References

[1]. Tiratricol inhibits yellow fever virus replication through targeting viral RNA-dependent RNA polymerase of NS5. Antiviral Res. 2023 Nov;219:105737.

[2]. Tiratricol neutralizes bacterial endotoxins and reduces lipopolysaccharide-induced TNF-alpha production in the cell. Chem Biol Drug Des. 2008 Oct;72(4):320-8.

Additional Infomation
Tiratricol is a monocarboxylic acid that is (4-hydroxy-3,5-diiodophenyl)acetic acid in which the phenolic hydroxy group has been replaced by a 4-hydroxy-3-iodophenoxy group. It is a thyroid hormone analogue that has been used in the treatment of thyroid hormone resistance syndrome. It has a role as a thyroid hormone, an antiviral agent, an EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor, a nutraceutical, a human metabolite and an anti-obesity agent. It is an aromatic ether, a monocarboxylic acid, an organoiodine compound and a member of phenols.
A metabolite of T3 and T4 thyroid hormones; promoted for hyperlipidemia, localized lipodystrophy, and obesity. Tiratricol has been used in trials studying the treatment of Allan-Herndon-Dudley Syndrome.
Tiratricol (also known as TRIAC or triiodothyroacetic acid) is a thyroid hormone analogue. It is indicated in the management of thyroid hormone resistance syndrome and is used, in combination with levothyroxine, to suppress thyroid-stimulating hormone production in patients with thyroid cancer. It has been investigated for use in reducing goiter. It has also shown some effectiveness in reducing the atrophy caused when using corticosteroids. Tiratricol has also been widely marketed, under various trade names, as a weight loss aid. In 1999 and 2000, the United States Food and Drug Administration and Health Canada both issued warnings to the public regarding the use of dietary supplements containing tiratricol. Tiratricol is not approved for sale in Canada or the United States. It was once an approved drug in Brazil, but its marketing authorization was suspended in 2003, effectively prohibiting its sale. (Wikipedia)
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H9I3O4
Molecular Weight
621.9354
Exact Mass
621.763
CAS #
51-24-1
Related CAS #
1477-04-9 (hydrochloride salt)
PubChem CID
5803
Appearance
White to off-white solid powder
Density
2.5±0.1 g/cm3
Boiling Point
531.6±50.0 °C at 760 mmHg
Melting Point
181.5ºC
Flash Point
275.3±30.1 °C
Vapour Pressure
0.0±1.5 mmHg at 25°C
Index of Refraction
1.767
LogP
5.47
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
21
Complexity
356
Defined Atom Stereocenter Count
0
InChi Key
UOWZUVNAGUAEQC-UHFFFAOYSA-N
InChi Code
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)
Chemical Name
2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
Synonyms
triiodothyroacetic acid; TRIAC; Tiratricol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 42 mg/mL (~67.53 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.02 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (4.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.6079 mL 8.0394 mL 16.0787 mL
5 mM 0.3216 mL 1.6079 mL 3.2157 mL
10 mM 0.1608 mL 0.8039 mL 1.6079 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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