Dextrothyroxine

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 serum.[3]

Dextrothyroxine

Clinical data
Trade names	Choloxin
Other names	D-3,5,3',5'-tetraiodothyronine
AHFS/Drugs.com	Multum Consumer Information
Pregnancy category	US: B (No risk in non-human studies)
ATC code	C10AX01 (WHO)
Legal status
Legal status	Discontinued
Identifiers
IUPAC name (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
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

See also

• Levothyroxine

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. PMID 9440092.