NAV

Tiratricol

Identification

Generic Name
Tiratricol
DrugBank Accession Number
DB03604
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 621.9323
Monoisotopic: 621.763489036
Chemical Formula
C14H9I3O4
Synonyms
  • 3,5,3'-Triiodothyroacetate
  • 3',3,5-Triiodothyroacetic acid
  • Tiratricol
  • Tiratricolum
  • Triacana
  • Triiodothyroacetic acid
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThyroid hormone receptor betaNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AcalabrutinibThe therapeutic efficacy of Tiratricol can be decreased when used in combination with Acalabrutinib.
AcarboseTiratricol may decrease the hypoglycemic activities of Acarbose.
AcebutololThe therapeutic efficacy of Tiratricol can be decreased when used in combination with Acebutolol.
AcenocoumarolThe risk or severity of bleeding can be increased when Tiratricol is combined with Acenocoumarol.
AcetohexamideTiratricol may decrease the hypoglycemic activities of Acetohexamide.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tiratricol sodium3HK9045D541477-04-9BBBAIWCYEJXUMH-UHFFFAOYSA-M

Categories

ATC Codes
H03AA04 — TiratricolD11AX08 — Tiratricol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Diphenylethers
Alternative Parents
Diarylethers / Phenoxy compounds / Phenol ethers / O-iodophenols / Iodobenzenes / 1-hydroxy-2-unsubstituted benzenoids / Aryl iodides / Monocarboxylic acids and derivatives / Carboxylic acids / Organoiodides
show 3 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2-halophenol / 2-iodophenol / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Diaryl ether
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
29OQ9EU4R1
CAS number
51-24-1
InChI Key
UOWZUVNAGUAEQC-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
SMILES
OC(=O)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1

References

General References
Not Available
PubChem Compound
5803
PubChem Substance
46504696
ChemSpider
5598
BindingDB
18862
RxNav
13982
ChEMBL
CHEMBL41632
ZINC
ZINC000004217580
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
4HY
Wikipedia
Tiratricol
PDB Entries
1nq0 / 1nq1 / 1nq2 / 1nuo / 2pin / 2pit / 2piu / 2pkl / 2qpy / 3d57 …
show 3 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentAllan-Herndon-Dudley Syndrome / Monocarboxylate Transporter 8 Deficiency1
2Active Not RecruitingTreatmentAllan-Herndon-Dudley Syndrome1
2CompletedTreatmentAllan-Herndon-Dudley Syndrome1
Not AvailableAvailableNot AvailableAllan-Herndon-Dudley Syndrome / Monocarboxylate Transporter 8 Deficiency1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00539 mg/mLALOGPS
logP5.27ALOGPS
logP5.59Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.31Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area66.76 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity105.67 m3·mol-1Chemaxon
Polarizability40.54 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6831
Blood Brain Barrier+0.7944
Caco-2 permeable+0.628
P-glycoprotein substrateNon-substrate0.5904
P-glycoprotein inhibitor INon-inhibitor0.8432
P-glycoprotein inhibitor IINon-inhibitor0.9274
Renal organic cation transporterNon-inhibitor0.8986
CYP450 2C9 substrateNon-substrate0.7944
CYP450 2D6 substrateNon-substrate0.9201
CYP450 3A4 substrateNon-substrate0.6595
CYP450 1A2 substrateInhibitor0.7505
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.9333
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8679
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6166
Ames testNon AMES toxic0.9047
CarcinogenicityNon-carcinogens0.8759
BiodegradationNot ready biodegradable0.975
Rat acute toxicity3.8459 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.939
hERG inhibition (predictor II)Non-inhibitor0.8942
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0000009000-fdaa79a11f1065901dd0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000039000-b107e72c5f4d1f4d0eb3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0000009000-33608c15d21468ea0a32
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000090000-d782821bc95e217a6b7b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ug3-0004930000-2968f354e3dda5f91fef
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1931700000-05f095ba78c3b7631bcb
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.7620544
predicted
DarkChem Lite v0.1.0
[M-H]-195.8199
predicted
DeepCCS 1.0 (2019)
[M+H]+179.8836544
predicted
DarkChem Lite v0.1.0
[M+H]+198.1779
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.0808544
predicted
DarkChem Lite v0.1.0
[M+Na]+204.84209
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Thyroid hormone receptor beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.
Gene Name
THRB
Uniprot ID
P10828
Uniprot Name
Thyroid hormone receptor beta
Molecular Weight
52787.16 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Transporters

Details1. Sodium/bile acid cotransporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
References
  1. Donkers JM, Zehnder B, van Westen GJP, Kwakkenbos MJ, IJzerman AP, Oude Elferink RPJ, Beuers U, Urban S, van de Graaf SFJ: Reduced hepatitis B and D viral entry using clinically applied drugs as novel inhibitors of the bile acid transporter NTCP. Sci Rep. 2017 Nov 10;7(1):15307. doi: 10.1038/s41598-017-15338-0. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 14, 2023 09:13