3,5-DIIODOTHYROPROPIONIC ACID

Investigational

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

Structure of 3,5-DIIODOTHYROPROPIONIC ACID

Structure Search

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)

HIDE SMILES / InChI

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

Description
Sources: https://adisinsight.springer.com/drugs/800040074 | https://www.ncbi.nlm.nih.gov/pubmed/1403782

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

Targets

Primary Target	Pharmacology	Condition	Potency
Thyroid hormone receptor 6 Target ID: CHEMBL2111462 Sources: https://adisinsight.springer.com/drugs/800004758 \| https://www.ncbi.nlm.nih.gov/pubmed/19506112	Agonist 2678

PubMed

Title	Date	PubMed
Thyroid hormone analogs for treatment of hypercholesterolemia and heart failure: past, present and future prospects.	2004 Dec	15572044
DITPA stimulates arteriolar growth and modifies myocardial postinfarction remodeling.	2004 May	15072976
A thyroid hormone analog with reduced dependence on the monocarboxylate transporter 8 for tissue transport.	2009 Sep	19497976
The cardiovascular effects of hyperthyroidism.	2010 Apr-Jun	20661186
Thyroid replacement therapy and heart failure.	2010 Jul 27	20660814

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

3,5-Diiodothyropropionic acid (DITPA) was observed to induce alpha-MHC mRNA in heart cell culture with EC50 approximately 5 x 10(-7) M.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:34:28 UTC 2023` Edited by `admin` on `Fri Dec 15 15:34:28 UTC 2023`
Record UNII	1HTO2X0SJ9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3,5-DIIODOTHYROPROPIONIC ACID

Common Name

English

3-(4-(4-HYDROXYPHENOXY)-3,5-DIIODOPHENYL)PROPANOIC ACID

Systematic Name

English

DITPA

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

395613