Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H12I2O4 |
| Molecular Weight | 510.0623 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1
InChI
InChIKey=WONYMNWUJVKVII-UHFFFAOYSA-N
InChI=1S/C15H12I2O4/c16-12-7-9(1-6-14(19)20)8-13(17)15(12)21-11-4-2-10(18)3-5-11/h2-5,7-8,18H,1,6H2,(H,19,20)
| Molecular Formula | C15H12I2O4 |
| Molecular Weight | 510.0623 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
3,5-Diiodothyropropionic acid (DITPA), a carboxylic acid analog with low metabolic activity, was observed to induce alpha-MHC mRNA in heart cell culture with EC50 approximately 5 x 10(-7) M. Zarion Pharmaceuticals was developing DITPA (3,5-diiodothyropropionic acid), a thyroid hormone analogue, for the treatment of Allan-Herndon-Dudley syndrome. In May 2013, the US FDA granted DITPA orphan drug status for the treatment of Allan-Herndon-Dudley syndrome. However, development of DITPA for the treatment of Allan-Herndon-Dudley syndrome was discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The cardiovascular effects of hyperthyroidism. | 2010-07-28 |
|
| Thyroid replacement therapy and heart failure. | 2010-07-27 |
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| Human platelet aggregation and degranulation is induced in vitro by L-thyroxine, but not by 3,5,3'-triiodo-L-thyronine or diiodothyropropionic acid (DITPA). | 2010-06 |
|
| Diiodothyropropionic acid: WO2008106213. | 2010-04 |
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| Letter by Pingitore et al regarding article, "DITPA (3,5-diiodothyropropionic acid), a thyroid hormone analog to treat heart failure: phase II trial Veterans Affairs cooperative study". | 2010-03-16 |
|
| Effects of the thyromimetic agent diiodothyropropionic acid on body weight, body mass index, and serum lipoproteins: a pilot prospective, randomized, controlled study. | 2010-03 |
|
| Transcriptional profile of isoproterenol-induced cardiomyopathy and comparison to exercise-induced cardiac hypertrophy and human cardiac failure. | 2009-12-09 |
|
| Regulation of arteriolar density in adult myocardium during low thyroid conditions. | 2009-09-11 |
|
| A thyroid hormone analog with reduced dependence on the monocarboxylate transporter 8 for tissue transport. | 2009-09 |
|
| DITPA (3,5-Diiodothyropropionic Acid), a thyroid hormone analog to treat heart failure: phase II trial veterans affairs cooperative study. | 2009-06-23 |
|
| Thyroid hormone analog 3,5-diiodothyropropionic acid promotes healthy vasculature in the adult myocardium independent of thyroid effects on cardiac function. | 2009-05 |
|
| Thyroid hormone-induced angiogenesis. | 2009-01 |
|
| Effects of thyroidectomy, T4, and DITPA replacement on brain blood vessel density in adult rats. | 2008-05 |
|
| Metabolic effects of thyroid hormone derivatives. | 2008-02 |
|
| Regulation of gene expression in rats with heart failure treated with the thyroid hormone analog 3,5-diiodothyropropionic acid (DITPA) and the combination of DITPA and captopril. | 2007-11 |
|
| Thyroid hormone analog, diiodothyropropionic acid (DITPA), exerts beneficial effects on chamber and cellular remodeling in cardiomyopathic hamsters. | 2007-07-07 |
|
| A phosphorimager-based filter binding thyroid hormone receptor competition assay for chemical screening. | 2006-10-26 |
|
| DITPA restores the repolarizing potassium currents Itof and Iss in cardiac ventricular myocytes of diabetic rats. | 2006-07-24 |
|
| Thyroid hormones and 3,5-diiodothyropropionic acid: new keys for new locks. | 2006-04 |
|
| Proangiogenesis action of the thyroid hormone analog 3,5-diiodothyropropionic acid (DITPA) is initiated at the cell surface and is integrin mediated. | 2006-04 |
|
| Action of topical thyroid hormone analogues on glucocorticoid-induced skin atrophy in mice. | 2006-03 |
|
| Thyroid (dys)function in heart failure: is it a potential target for medical treatment? | 2005 |
|
| Thyroid hormone analogs for treatment of hypercholesterolemia and heart failure: past, present and future prospects. | 2004-12 |
|
| Thyroid hormone analog, DITPA, improves endothelial nitric oxide and beta-adrenergic mediated vasorelaxation after myocardial infarction. | 2004-10 |
|
| Regulation of gene expression in cardiomyocytes by thyroid hormone and thyroid hormone analogs 3,5-diiodothyropropionic acid and CGS 23425 [N-[3,5-dimethyl-4-(4'-hydroxy-3'-isopropylphenoxy)-phenyl]-oxamic acid]. | 2004-10 |
|
| DITPA stimulates arteriolar growth and modifies myocardial postinfarction remodeling. | 2004-05 |
|
| Effects of thyroid hormone on the cardiovascular system. | 2004 |
|
| DITPA stimulates bFGF, VEGF, angiopoietin, and Tie-2 and facilitates coronary arteriolar growth. | 2003-02 |
|
| Slowing of the inactivation of cardiac voltage-dependent sodium channels by the amiodarone derivative 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (KB130015). | 2003-01 |
|
| Clinical and experimental studies on the use of 3,5-diiodothyropropionic acid, a thyroid hormone analogue, in heart failure. | 2002-06 |
|
| Pilot studies on the use of 3,5-diiodothyropropionic acid, a thyroid hormone analog, in the treatment of congestive heart failure. | 2002 |
Sample Use Guides
Study of 3,5-Diiodothyropropionic Acid (DITPA) in Hypercholesterolemic Patients:
Sixty (60) patients will be randomized to 1 of 3 treatment groups in a 1:1:1 ratio (i.e., 20 patients per treatment group):
DITPA at 90 mg/day (45 mg twice a day [BID] taken orally)
DITPA at 180 mg/day (90 mg BID taken orally)
Those patients randomized to receive DITPA at 90 mg/day will receive 45 mg/day for the first 2 weeks, followed by 90 mg/day for 10 weeks.
Those patients randomized to receive DITPA at 180 mg/day will receive 45 mg/day for the first 2 weeks, followed by 90 mg/day for the next 2 weeks, and then 180 mg/day for 8 weeks.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:01:37 GMT 2025
by
admin
on
Mon Mar 31 18:01:37 GMT 2025
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| Record UNII |
1HTO2X0SJ9
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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Systematic Name | English |
| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
395613
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FDA ORPHAN DRUG |
764420
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EU-Orphan Drug |
EU/3/13/1193
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100000178209
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134267
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160565
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DB12629
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DTXSID8040939
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1158-10-7
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1HTO2X0SJ9
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| Related Record | Type | Details | ||
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TARGET -> AGONIST |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |
