Dextrothyroxine - Misplaced Pages

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)
Legal status
Legal status	Discontinued
Identifiers
IUPAC name (2R)-2-amino-3-propanoic acid
CAS Number	51-49-0
PubChem CID	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
3D model (JSmol)	Interactive image
SMILES O=C(O)(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 name Choloxin) is a dextrorotary isomer of thyroxine. It saw research as a cholesterol-lowering drug but was pulled due to cardiac side-effects. It increases hepatic lipase which in turn improves utilization of triglycerides and decreases levels of lipoprotein(a) in blood serum.

References

"Dextrothyroxine (Code C61719)". NCI Thesaurus. National Cancer Institute. 2011-11-14. Retrieved 2020-01-28.
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 as psyllium and glucomannan

Statins (HMG-CoA reductase, LDL)	Atorvastatin Cerivastatin Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin
Niacin and derivatives (HDL and LDL)	Acipimox Aluminium nicotinate Niacin 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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