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Dextrothyroxine

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Chemical compound

Pharmaceutical compound

Dextrothyroxine
Clinical data

Trade names	Choloxin
Other names	D-3,5,3',5'-tetraiodothyronine
AHFS/Drugs.com	Multum Consumer Information
ATC code	C10AX01 (WHO)
Identifiers
IUPAC name (2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
CAS Number	51-49-0
PubChemCID	8730
DrugBank	DB00509
ChemSpider	8402
UNII	4W9K63FION
ChEBI	CHEBI:30659
ChEMBL	ChEMBL559
CompTox Dashboard(EPA)	DTXSID60199000
ECHA InfoCard	100.000.094
Chemical and physical data
Formula	C₁₅H₁₁I₄NO₄
Molar mass	776.874 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(O)[C@H](N)Cc2cc(I)c(Oc1cc(I)c(O)c(I)c1)c(I)c2
InChI 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 Key:XUIIKFGFIJCVMT-GFCCVEGCSA-N

Dextrothyroxine (trade nameCholoxin) is adextrorotary isomer ofthyroxine.^[1] It saw research as acholesterol-lowering drug^[2] but was pulled due to cardiac side-effects. It increaseshepatic lipase which in turn improves utilization oftriglycerides and decreases levels oflipoprotein(a) inblood serum.^[3]

^"Dextrothyroxine (Code C61719)".NCI Thesaurus. National Cancer Institute. 2011-11-14. Retrieved2020-01-28.
^Bantle JP, Hunninghake DB, Frantz ID, Kuba K, Mariash CN, Oppenheimer JH (September 1984). "Comparison of effectiveness of thyrotropin-suppressive doses of D- and L-thyroxine in treatment of hypercholesterolemia".The American Journal of Medicine.77 (3):475–81.doi:10.1016/0002-9343(84)90107-4.PMID 6475988.
^Bommer C, Werle E, Walter-Sack I, Keller C, Gehlen F, Wanner C, et al. (January 1998). "D-thyroxine reduces lipoprotein(a) serum concentration in dialysis patients".Journal of the American Society of Nephrology.9 (1):90–6.doi:10.1681/ASN.V9190.PMID 9440092.

Cholesterol absorption inhibitors,NPC1L1	Ezetimibe Hyzetimibe SCH-48461
Bile acid sequestrants/resins (LDL)	Colesevelam Colestilan Colestipol Colestyramine Colextran Soluble fiber such aspsyllium andglucomannan

Statins (HMG-CoA reductase,LDL)	Atorvastatin Cerivastatin^‡ Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin^#
Niacin and derivatives (HDL andLDL)	Acipimox Aluminium nicotinate Nicotinic acid Niceritrol Nicofuranose Nicotinyl alcohol
MTTP inhibitors (VLDL)	Dirlotapide Lomitapide Mitratapide
ATP citrate lyase inhibitors (LDL)	Bempedoic acid
Thyromimetics (VLDL)	Dextrothyroxine^‡ Resmetirom

Fibrates	Aluminium clofibrate Bezafibrate Choline fenofibrate Ciprofibrate Clinofibrate Clofibrate^‡ Clofibride Etofibrate Fenofibrate Gemfibrozil Nafenopin Pemafibrate Ronifibrate Simfibrate
Others	GW501516^§

ANGPTL3 inhibitors (LDL/HDL)

Combinations

Other

THRTooltip Thyroid hormone receptor

Agonists	Dextrothyroxine DIMIT DITPA Levothyroxine Liothyronine Liotrix Thyroxine Tiratricol (TRIAC) Triiodothyronine Thyroid extract
Thyromimetics (selective agonists)	Eprotirome (KB-2115) KB-141 KB-2611 KB-130015 MB-07344 MB-07811 Resmetirom Sobetirome (GC-1, GRX-431) VK-0214 VK-2809 ZYT1
Antagonists	1-850 NH3 Tetraiodothyroacetic acid (Tetrac)

NISTooltip Sodium-iodide symporter	Inhibitors:Cyanogenic glycosides Perchlorates (e.g.,potassium perchlorate) Pertechnetates (e.g.,sodium pertechnetate) Thiocyanates

TPOTooltip Thyroid peroxidase	Inhibitors:Benzylthiouracil Carbimazole Genistein Methimazole Methylthiouracil Propylthiouracil 2-Thiouracil Thiourea
DIOTooltip Iodothyronine deiodinase	Inhibitors:Dexpropranolol Iopanoic acid Ipodate sodium (sodium iopodate) Propranolol Propylthiouracil

Others

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