DEXTROTHYROXINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H11I4NO4
Molecular Weight	776.87
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O

InChI

InChIKey=XUIIKFGFIJCVMT-GFCCVEGCSA-N

InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H11I4NO4
Molecular Weight	776.87
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB00509
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68003918

Dextrothyroxine is the dextrorotary isomer of the synthetic thyroxine. It is an antihyperlipidemic agent. The mechanism of action is not completely understood, but dextrothyroxine apparently acts in the liver to stimulate formation of low-density lipoprotein (LDL) and, to a much greater extent, to increase catabolism of LDL. This leads to increased excretion of cholesterol and bile acids via the biliary route into the feces, with a resulting reduction in serum cholesterol and LDL. Dextrothyroxine has no significant effect on high-density lipoproteins (HDL). Inherently, it will also bind to thyroid receptors and as it is a prohormone, it will bind as a substrate to iodide peroxidase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thyroid hormone receptor 6 Target ID: CHEMBL2111462 Sources: https://www.drugbank.ca/drugs/DB00509	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypercholesterolemia 47 Sources: https://www.drugbank.ca/drugs/DB00509	Primary		Approved 8429	CHOLOXIN Approved Use Used to lower high cholesterol levels in the blood. Launch Date -8.5795201E10

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 day REVIEW https://pubmed.ncbi.nlm.nih.gov/363332/	6 mg 1 times / day unknown, oral dose: 6 mg route of administration: Oral experiment type: UNKNOWN co-administered:		LEVOTHYROXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% REVIEW https://pubmed.ncbi.nlm.nih.gov/363332/	6 mg 1 times / day unknown, oral dose: 6 mg route of administration: Oral experiment type: UNKNOWN co-administered:		LEVOTHYROXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
8 mg 1 times / day steady, oral (max) Recommended Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/	unhealthy, adult n = 18 Health Status: unhealthy Condition: diabetic Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/	Disc. AE: Loss of control of diabetes, Acidosis... Other AEs: Blood cholesterol decreased... AEs leading to discontinuation/dose reduction: Loss of control of diabetes (8 patients) Acidosis (1 patient) Hypoglycemic reaction (2 patients) Other AEs: Blood cholesterol decreased (18 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/

AEs

AE	Significance	Dose	Population
Acidosis	1 patient Disc. AE	8 mg 1 times / day steady, oral (max) Recommended Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/	unhealthy, adult n = 18 Health Status: unhealthy Condition: diabetic Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/
Blood cholesterol decreased	18 patients	8 mg 1 times / day steady, oral (max) Recommended Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/	unhealthy, adult n = 18 Health Status: unhealthy Condition: diabetic Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/
Hypoglycemic reaction	2 patients Disc. AE	8 mg 1 times / day steady, oral (max) Recommended Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/	unhealthy, adult n = 18 Health Status: unhealthy Condition: diabetic Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/
Loss of control of diabetes	8 patients Disc. AE	8 mg 1 times / day steady, oral (max) Recommended Dose: 8 mg, 1 times / day Route: oral Route: steady Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/	unhealthy, adult n = 18 Health Status: unhealthy Condition: diabetic Age Group: adult Sex: unknown Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/14204552/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-047088	http://www.3bsc.com/index/pro_info.php?id=83740
AA Blocks	AA006VP2	https://www.aablocks.com/goods/Goods/detail?id=AA006VP2
AEchem Scientific Corp., USA	AE029677	http://www.aechemsc.com/info_products/AE029677.php
AHH Chemical co.,ltd	MB-00564	http://www.ahhchemical.com/product/MB-00564.html
AHH Chemical co.,ltd	MT-50746	http://www.ahhchemical.com/product/MT-50746.html
Aaron Chemicals	AR006WGU	http://www.aaronchem.com/51-49-0
Achemtek	0104-042131	http://www.achemtek.com/51-49-0
Alichem	19113114	http://www.alichem.com/en/products/51-49-0.html
Angene	AGN-PC-0OBILQ	http://www.angenechemical.com/productshow/AGN-PC-0OBILQ.html
Anward	ANW-63155	http://www.anward.com/pro_result/49606
Aurora Fine Chemicals LLC	A17.915.702	http://online.aurorafinechemicals.com/info?ID=A17.915.702
BLD Pharm	BD33885	http://www.bldpharm.com/products/51-49-0.html
Chemenu	CM129121	http://www.chemenu.com/products/CM129121
Chemspace	CSSB00000092231	https://chem-space.com/CSSB00000092231
DC Chemicals	DC31645	http://www.dcchemicals.com//product_show-Biotirmone.html
Glentham Life Sciences	GM9007	http://www.glentham.com/products/product/GM9007/
LGC Standards	LGCFOR1813.01	https://www.lgcstandards.com/US/en/p/LGCFOR1813.01
LGC Standards	MM1813.01	https://www.lgcstandards.com/US/en/p/MM1813.01
Lab Network	LN00337290	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00337290
MuseChem	R046180	https://www.musechem.com/product/R046180.html
OChem	11916	http://www.ocheminc.com/index.php?act=psearch&pid=051T490
Sigma-Aldrich	R751804_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/r751804
Sigma-Aldrich	T34908_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/t34908?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S525805	http://www.smolecule.com/products/s525805
Smolecule	S793415	https://www.smolecule.com/products/s793415
THE BioTek	bt-267396	https://www.thebiotek.com/product/inhibitors/bt-267396
abcr GmbH	AB142563	http://www.abcr.com/shop/en/AB142563
eNovation Chemicals	D673948	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673948
eNovation Chemicals	D765759	https://www.enovationchem.com/ProductDetails.asp?ProductID=D765759
eNovation Chemicals	D957539	https://www.enovationchem.com/ProductDetails.asp?ProductID=D957539
iChemical	EBD2197960	http://www.ichemical.com/products/51-49-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Evaluation of a hypocholesterolemic agent. Dextrothyroxine sodium (Choloxin).	1969 May 12	5818672
Dextrothyroxine for lowering cholesterol.	1976 Jun 18	934018
Effects of dextrothyroxine on the pituitary-thyroid axis in hypercholesterolemic children and goitrous adults.	1980 Dec	6777394
Treatment of heterozygous familial hypercholesterolemia with lipid-lowering drugs.	1989 Jan-Feb	2492189
Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition.	2002 Apr	11901210
Nuclear receptor agonists stimulate release of arachidonic acid from rat liver cells.	2002 Dec	12468267
Inhibition of the activity of the native gamma-aminobutyric acid A receptor by metabolites of thyroid hormones: correlations with molecular modeling studies.	2004 Apr 9	15033424
Simultaneous determination of l-thyroxine (l-T(4)), d-thyroxine (d-T(4)), and l-triiodothyronine (l-T(3)) using a sensors/sequential injection analysis system.	2004 Sep 8	18969581
Short-term stimulation of lipogenesis by 3,5-L-diiodothyronine in cultured rat hepatocytes.	2005 Sep	15932927
A child with resistance to thyroid hormone without thyroid hormone receptor gene mutation: a 20-year follow-up.	2008 Jan	18302516
In-line coupling of a reversed-phase column to cope with limited chemoselectivity of a quinine carbamate-based anion-exchange type chiral stationary phase.	2008 Jun	18428182
Resistance to thyroid hormone with missense mutation (V349M) in the thyroid hormone receptor beta gene.	2008 Mar	18363280
[Therapeutic possibilities in patients with selective pituitary resistance to thyroid hormones].	2008 Mar 15	18373914
9 years follow-up of a patient with pituitary form of resistance to thyroid hormones (PRTH): comparison of two treatment periods of D-thyroxine and triiodothyroacetic acid (TRIAC).	2009 Oct	20020587
Safety and efficacy of laropiprant and extended-release niacin combination in the management of mixed dyslipidemias and primary hypercholesterolemia.	2010	21701618
Enatioselective quantitative separation of D- and L-thyroxine by molecularly imprinted micro-solid phase extraction silver fiber coupled with complementary molecularly imprinted polymer-sensor.	2010 Jun 25	20483419
Layer-by-layer assembled molecularly imprinted polymer modified silver electrode for enantioselective detection of D- and L-thyroxine.	2010 Nov 29	21035598

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

The relative binding affinities of liothyronine (L-T3), levothyroxine (L-T4), D-triiodothyronine (D-T3), and dextrothyroxine (D-T4) were measured in vitro. Solubilized nuclear receptors were prepared from rat anterior pituitaries. L-T3 had the highest binding for the nuclear receptor (taken as 100%). L-T4 and D-T3 binded to the nuclear receptor with similar affinities (11% and 13%, respectively), while the affinity of D-T4 represents only 3% that of L-T3.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:10:56 UTC 2023` Edited by `admin` on `Fri Dec 15 15:10:56 UTC 2023`
Record UNII	4W9K63FION
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXTROTHYROXINE

Common Name

English

DEXTROTHYROXINE [VANDF]

Common Name

English

D-THYROXINE [MI]

Common Name

English

Dextrothyroxine [WHO-DD]

Common Name

English

D-THYROXINE

Common Name

English

D-TYROSINE, O-(4-HYDROXY-3,5-DIIODOPHENYL)-3,5-DIIODO-

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QC10AX01