Levothyroxine (CED0001161)

Record Information
Version1.0
Creation Date2016-05-22 03:42:46 UTC
Update Date2026-08-19 08:59:40 UTC
Accession NumberCHEM016756
Identification
Common NameLevothyroxine
ClassSmall Molecule
Description
Levothyroxine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 776.87 g/mol, Levothyroxine is a heavy molecule. It has the chemical formula C15H11I4NO4 and functions biologically as a thyroid hormone (PMC5811372). The compound is used as a treatment for hypothyroidism (PMC12695664, PMC12765874, PMC13024578, PMC1492602, PMC9869701). Its recorded protein targets include the thyroid hormone receptor alpha (THRA), thyroid hormone receptor beta (THRB), integrin alpha-V (ITGAV), and integrin beta-3 (ITGB3), where it acts as an agonist or binder. Levothyroxine is found in or released from 20 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used in thyroid preparations. Other sources include food, food processing, and cookware, specifically in food preservation, processing meats, and the preparation of vinegar. It is also associated with household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, tobacco product moisture control, non-electric simulated smoking devices, and cigar cigarettes. Additionally, it is found in electrical and electronic equipment, including antennas, electric switches, auxiliary devices, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for the compound include oral, intravenous, intramuscular, and topical administration.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
3,3',5,5'-Tetraiodo-L-thyronineChEBI
3,5,3',5'-TETRAIODO-L-thyronineChEBI
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanineChEBI
L-T4ChEBI
LevothyroxinChEBI
LevothyroxineChEBI
LT4ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosineChEBI
T4ChEBI
L-ThyroxineKegg
O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosineKegg
3,5,3'5'-Tetraiodo-L-thyronineKegg
ForthyronKegg
(-)-ThyroxineHMDB
3,3',5,5''-tetraiodo-L-ThyronineHMDB
3,5,3',5'-TetraiodothyronineHMDB, MeSH
D-ThyroxineHMDB
DL-ThyroxinHMDB
HenningHMDB
L-3,5,3',5'-TetraiodothyronineHMDB, MeSH
L-ThyroxinHMDB
LaevothyroxinumHMDB
LevothroidHMDB, MeSH
Levothyroxine sodiumHMDB, MeSH
LevothyroxinumHMDB
LevoxylHMDB, MeSH
Prestwick_548HMDB
SynthroidHMDB, MeSH
TetraiodothyronineHMDB
TetrametHMDB
THXHMDB
ThyratabsHMDB
ThyraxHMDB, MeSH
ThyreoideumHMDB
ThyroxinHMDB, MeSH
ThyroxinalHMDB
Thyroxine I 125HMDB
Thyroxine iodineHMDB
Allphar brand OF levothyroxine sodiumMeSH, HMDB
BerlthyroxMeSH, HMDB
Delalande, levothyroxinMeSH, HMDB
DexnonMeSH, HMDB
EferoxMeSH, HMDB
EltroxinMeSH, HMDB
Kern brand OF levothyroxine sodiumMeSH, HMDB
L-ThyroxMeSH, HMDB
L-Thyroxin henningMeSH, HMDB
L-Thyroxin betaMeSH, HMDB
L-Thyroxine rocheMeSH, HMDB
Levothyroxin deladandeMeSH, HMDB
LévothyroxMeSH, HMDB
Merck lipha santé brand OF levothyroxine sodiumMeSH, HMDB
Nourypharma brand OF levothyroxine sodiumMeSH, HMDB
OroxineMeSH, HMDB
Aventis brand OF levothyroxine sodiumMeSH, HMDB
EuthyroxMeSH, HMDB
EutiroxMeSH, HMDB
Forest brand OF levothyroxine sodiumMeSH, HMDB
Genpharm brand OF levothyroxine sodiumMeSH, HMDB
GlaxoSmithKline brand OF levothyroxine sodiumMeSH, HMDB
Goldshield brand OF levothyroxine sodiumMeSH, HMDB
LThyroxin henningMeSH, HMDB
levo-TMeSH, HMDB
Sanofi synthelabo brand OF levothyroxine sodiumMeSH, HMDB
Sigma brand OF levothyroxine sodiumMeSH, HMDB
SynthroxMeSH, HMDB
ThevierMeSH, HMDB
Watson brand OF levothyroxine sodiumMeSH, HMDB
Berlin chemie brand OF levothyroxine sodiumMeSH, HMDB
Delalande brand OF levothyroxine sodiumMeSH, HMDB
EltroxineMeSH, HMDB
Hexal brand 2 OF levothyroxine sodiumMeSH, HMDB
L Thyroxine rocheMeSH, HMDB
NovothyralMeSH, HMDB
TiroidineMeSH, HMDB
Vortex brand OF levothyroxine sodiumMeSH, HMDB
Abbot brand OF levothyroxine sodiumMeSH, HMDB
Berlin-chemie brand OF levothyroxine sodiumMeSH, HMDB
Byk brand OF levothyroxine sodiumMeSH, HMDB
Deladande, levothyroxinMeSH, HMDB
GlaxoWellcome brand OF levothyroxine sodiumMeSH, HMDB
Henning berlin brand OF levothyroxine sodiumMeSH, HMDB
Hexal brand 1 OF levothyroxine sodiumMeSH, HMDB
L ThyroxMeSH, HMDB
L Thyroxin henningMeSH, HMDB
L Thyroxin betaMeSH, HMDB
L ThyroxineMeSH, HMDB
LThyroxin betaMeSH, HMDB
leo, TiroxinaMeSH, HMDB
levo TMeSH, HMDB
LevoTMeSH, HMDB
LevothyroidMeSH, HMDB
Levothyroxin delalandeMeSH, HMDB
LevoxineMeSH, HMDB
Merck brand OF levothyroxine sodiumMeSH, HMDB
Monarch brand OF levothyroxine sodiumMeSH, HMDB
Mova brand OF levothyroxine sodiumMeSH, HMDB
NovothyroxMeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosineMeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosineMeSH, HMDB
Roche brand OF levothyroxine sodiumMeSH, HMDB
Rudefsa brand OF levothyroxine sodiumMeSH, HMDB
Sodium levothyroxineMeSH, HMDB
T4 Thyroid hormoneMeSH, HMDB
Thyroid hormone, T4MeSH, HMDB
Tiroxina leoMeSH, HMDB
UnithroidMeSH, HMDB
Betapharm brand OF levothyroxine sodiumMeSH, HMDB
Chemical FormulaC15H11I4NO4
Average Molecular Mass776.870 g/mol
Monoisotopic Mass776.687 g/mol
CAS Registry Number51-48-9
IUPAC Name(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
Traditional Namelevothyroxine
SMILESN[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O
InChI IdentifierInChI=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-/m0/s1
InChI KeyXUIIKFGFIJCVMT-LBPRGKRZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • Diphenylether
  • Diaryl ether
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Phenoxy compound
  • Phenol ether
  • 2-halophenol
  • 2-iodophenol
  • Aralkylamine
  • Phenol
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Benzenoid
  • Monocyclic benzene moiety
  • Amino acid
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoiodide
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP1.15ALOGPS
logP3.73ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.27ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.79 m³·mol⁻¹ChemAxon
Polarizability49.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0f89-4002002900-0d489fed1cb888a2d9d0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ac9-0591664310-c9b7aec3184ebb20a2daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-2566449540-35bb942c7bcbcfe41af7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-3375497520-9dee3cb0c153e6c6df9eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-0001001900-83ff4aafed0b73c6c7b7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-6e0a640216afcce0837eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-9223d3d63e3db43052a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-1e8e674422aa4d820da7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0132219000-42259b5a596f74aec76fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0019217000-baafc92556cb18d71b3aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-bb154453510a75ca822cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-f785346765de92765afdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0000119000-af7b1e923ec5750514afNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f8j-1248309000-68eea5695ceb400ea5b0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0029337000-a85b59c3575dc95d36fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0003109000-480d647f8d49feeec28cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01si-0000000900-524d052a32c1fe4b904dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0000001900-553f6a4045ef2241fd85Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-d2431d885a79bb80b7a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000000900-137b5f8f48031bc9aa4fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-0004001900-db1d8cdb93785d786382Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0h9u-7029014300-3bd9620b0c6a8dd20c93Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000000900-95266ab7e52b7d3cb322Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1700000900-195c16ab7434b857e712Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-0dba40d354fa6a5575e0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000000900-d76aec17d3d890cb64c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0000001900-daf0bb8e065f55b0cda3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0001013900-6d1177cb9a243bb761ebNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
520.0Log mg/kg[290:920]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypothyroidismis_treatment_forNot AvailablePMC12695664 , PMC12765874 , PMC12765874 , PMC13024578 , PMC1492602 , PMC9869701
nodular goiteris_treatment_forNot AvailablePMC6291884
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
332Thyroid preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)0.311397
Click to view 3D structureSolute carrier organic anion transporter family member 1C1Q9ERB5Mus musculusPredicted (SEA)0.0778492
Thyroid hormone receptor alpha structureClick to view 3D structureThyroid hormone receptor alphaP10827HumansPredicted (SEA)0.0778492
Thyroid hormone receptor beta structureClick to view 3D structureThyroid hormone receptor betaP10828HumansPredicted (SEA)0.0778492
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)0.0778492
Click to view 3D structureThyroid hormone receptor betaP18113Rattus norvegicusPredicted (SEA)0.155698
Click to view 3D structureTyrosine 3-monooxygenaseP04177Rattus norvegicusPredicted (SEA)0.0778492
Retinoic acid receptor RXR-alpha structureClick to view 3D structureRetinoic acid receptor RXR-alphaP19793HumansPredicted (SEA)4.20386
Proliferating cell nuclear antigen structureClick to view 3D structureProliferating cell nuclear antigenP12004HumansPredicted (SEA)0.0778492
Click to view 3D structureSolute carrier organic anion transporter family member 4C1Q6ZQN7HumansPredicted (SEA)0.0778492
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)24.9896
Click to view 3D structureGlutamate receptor 2P19491Rattus norvegicusPredicted (SEA)1.01204
Click to view 3D structureGlutamate receptor 3P19492Rattus norvegicusPredicted (SEA)1.16774
Glutamate receptor 2 structureClick to view 3D structureGlutamate receptor 2P42262HumansPredicted (SEA)2.33548
Click to view 3D structureGlutamate receptor 1P19490Rattus norvegicusPredicted (SEA)12.6116
Click to view 3D structureUDP-glucuronosyltransferase 1A1P22309HumansPredicted (SEA)1.16774
Click to view 3D structureGlutamate racemaseQ03469Lactobacillus fermentumPredicted (SEA)5.76084
Click to view 3D structureGlutamate receptor 4P19493Rattus norvegicusPredicted (SEA)1.08989
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)240.243
Click to view 3D structureGlutamate receptor ionotropic, kainate 1P22756Rattus norvegicusPredicted (SEA)4.35956
Glutamate receptor 1 structureClick to view 3D structureGlutamate receptor 1P42261HumansPredicted (SEA)4.51525
Click to view 3D structureGlutamate receptor 4P48058HumansPredicted (SEA)2.10193
Glutamate receptor ionotropic, kainate 1 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 1P39086HumansPredicted (SEA)3.42537
Click to view 3D structureGlutamate receptor 3P42263HumansPredicted (SEA)1.32344
Click to view 3D structureGlutamate receptor ionotropic, kainate 5Q16478HumansPredicted (SEA)2.41333
Concentrations
Not Available
External Links
DrugBank IDDB00451
HMDB IDHMDB0000248
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLevothyroxine
Chemspider ID5614
ChEBI ID18332
PubChem Compound IDNot Available
Kegg Compound IDC01829
YMDB IDNot Available
ECMDB IDECMDB24025
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15206581
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18996189
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20483419
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2062236
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21035598
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24216002
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24548294
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24610609
9. Martinovich, V. P.; Katok, Ya. M.; Fil'chenkov, N. A.; Sviridov, O. V. Conjugated synthesis of L-thyroxine and L-triiodothyronine. Vestsi Natsyyanal'nai Akademii Navuk Belarusi, Seryya Khimichnykh Navuk (2004), (1), 85-92.
10. Martinovich, V. P.; Katok, Ya. M.; Fil'chenkov, N. A.; Sviridov, O. V. Conjugated synthesis of L-thyroxine and L-triiodothyronine. Vestsi Natsyyanal'nai Akademii Navuk Belarusi, Seryya Khimichnykh Navuk (2004), (1), 85-92.
11. Kahan IL, Varsanyi-Nagy M, Toth M, Nadrai A: The possible role of tear fluid thyroxine in keratoconus development. Exp Eye Res. 1990 Apr;50(4):339-43.
12. Jagannathan NR, Tandon N, Raghunathan P, Kochupillai N: Reversal of abnormalities of myelination by thyroxine therapy in congenital hypothyroidism: localized in vivo proton magnetic resonance spectroscopy (MRS) study. Brain Res Dev Brain Res. 1998 Aug 8;109(2):179-86.
13. Kurz W, Wittlinger G, Litmanovitch YI, Romanoff H, Pfeifer Y, Tal E, Sulman FG: Effect of manual lymph drainage massage on urinary excretion of neurohormones and minerals in chronic lymphedema. Angiology. 1978 Oct;29(10):764-72.
14. Randolph VS: Four clinical chemistry analyses for pediatric patients: glycosylated hemoglobin, free bilirubin, sweat electrolytes, neonatal thyroxine. Am J Med Technol. 1982 Jan;48(1):15-22.
15. van Wassenaer AG, Stulp MR, Valianpour F, Tamminga P, Ris Stalpers C, de Randamie JS, van Beusekom C, de Vijlder JJ: The quantity of thyroid hormone in human milk is too low to influence plasma thyroid hormone levels in the very preterm infant. Clin Endocrinol (Oxf). 2002 May;56(5):621-7.
16. Etling N, Gehin-Fouque F, Vielh JP, Gautray JP: The iodine content of amniotic fluid and placental transfer of iodinated drugs. Obstet Gynecol. 1979 Mar;53(3):376-80.
17. Zenovko EI, Pavlov BA, Koreshkov GG, Gudukina GN, Sonkina EG: [Hypothalamo-pituitary-thyroid system in patients with rheumatoid arthritis]. Ter Arkh. 1998;70(1):49-52.
18. Hays MT, McGuire RA, Hoogeveen JT, Diezeraad KN: Measurement method for radioactive thyroxine, triiodothyronine, iodide, and iodoprotein in samples with low activity. J Nucl Med. 1980 Mar;21(3):225-32.
19. Benvenga S, Alesci S, Trimarchi F: High-density lipoprotein-facilitated entry of thyroid hormones into cells: a mechanism different from the low-density lipoprotein-facilitated entry. Thyroid. 2002 Jul;12(7):547-56.
20. Gil'miiarova FN, Pervova IuV, Radomskaia VM, Gergel' NI, Tarasova SV: [Levels of unified metabolites and thyroid hormones in blood and oral fluid of children with minimal brain dysfunction]. Biomed Khim. 2004 Mar-Apr;50(2):204-10.
21. Hausman GJ, Wright JT, Latimer A, Watson R, Martin RJ: The influence of human growth hormone (GH) and thyroxine (T4) on the differentiation of adipose tissue in the fetus. Obes Res. 1993 Sep;1(5):345-56.
22. Gil-Loyzaga P, Remezal M, Mollicone R, Ibanez A, Oriol R: H and B human blood-group antigen expression in cochlear hair cells is modulated by thyroxine. Cell Tissue Res. 1994 May;276(2):239-43.
23. Escobar-Morreale HF, Botella-Carretero JI, Gomez-Bueno M, Galan JM, Barrios V, Sancho J: Thyroid hormone replacement therapy in primary hypothyroidism: a randomized trial comparing L-thyroxine plus liothyronine with L-thyroxine alone. Ann Intern Med. 2005 Mar 15;142(6):412-24.
24. Bode HH, Vanjonack WJ, Crawford JD: Mitigation of cretinism by breast-feeding. Pediatrics. 1978 Jul;62(1):13-6.
25. Marks P, Anderson J, Vincent R: Aldosterone in myxoedema. Lancet. 1978 Dec 16;2(8103):1277-8.
26. Sutherland RL, Simpson-Morgan MW: The thyroxine-binding properties of serum proteins. A competitive binding technique employing sephadex G-25. J Endocrinol. 1975 Jun;65(3):319-32.
27. Braley-Mullen H, Sharp GC: A thyroxine-containing thyroglobulin peptide induces both lymphocytic and granulomatous forms of experimental autoimmune thyroiditis. J Autoimmun. 1997 Dec;10(6):531-40.
28. Raghu P, Reddy GB, Sivakumar B: Inhibition of transthyretin amyloid fibril formation by 2,4-dinitrophenol through tetramer stabilization. Arch Biochem Biophys. 2002 Apr 1;400(1):43-7.
29. Hekimsoy Z, Oktem IK: Serum creatine kinase levels in overt and subclinical hypothyroidism. Endocr Res. 2005;31(3):171-5.
30. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.