Dextrothyroxine

Chemical compound
  • C10AX01 (WHO)
Legal statusLegal status
  • Discontinued
Identifiers
  • (2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]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 Edit this at Wikidata
ECHA InfoCard100.000.094 Edit this at WikidataChemical and physical dataFormulaC15H11I4NO4Molar mass776.874 g·mol−13D model (JSmol)
  • Interactive image
  • 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 name Choloxin) is a dextrorotary isomer of thyroxine.[1] It saw research as a cholesterol-lowering drug[2] 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.[3]

See also

References

  1. ^ "Dextrothyroxine (Code C61719)". NCI Thesaurus. National Cancer Institute. 2011-11-14. Retrieved 2020-01-28.
  2. ^ 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.
  3. ^ 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.
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GI tract
Cholesterol absorption inhibitors, NPC1L1
Bile acid sequestrants/resins (LDL)
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Niacin and derivatives (HDL and LDL)
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Receptor
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THRTooltip Thyroid hormone receptor
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(selective agonists)
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  • Tetraiodothyroacetic acid (Tetrac)
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NISTooltip Sodium-iodide symporter
 
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TPOTooltip Thyroid peroxidase
DIOTooltip Iodothyronine deiodinase
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  • See also: Receptor/signaling modulators
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