1.02011-04-11 17:18:27 UTC2015-10-09 22:30:38 UTCFDB021829LevothyroxineThe thyronamines function via some unknown mechanism to inhibit neuronal activity; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature.; Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles. (If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in goitre.) Via a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues in the thyroglobulin molecules, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one particle of MIT and one particle of DIT produces triiodothyronine.; Both T3 and T4 are used to treat thyroid hormone deficiency (hypothyroidism). They are both absorbed well by the gut, so can be given orally. Levothyroxine, the most commonly used synthetic thyroxine form, is a stereoisomer of physiological thyroxine, which is metabolized more slowly and hence usually only needs once-daily administration. Natural desiccated thyroid hormones, which are derived from pig thyroid glands, are a "natural" hypothyroid treatment containing 20% T3 and traces of T2, T1 and calcitonin.; this plays an important role in the hibernation cycles of mammals. One effect of administering the thyronamines is a severe drop in body temperature.; The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism.; The thyronamines function via some unknown mechanism to inhibit neuronal activity [HMDB](-)-Thyroxine3,3',5,5'-Tetraiodo-L-thyronine3,3',5,5''-tetraiodo-L-thyronine3,5,3',5'-TETRAIODO-L-thyronine3,5,3',5'-Tetraiodothyronine3,5,3'5'-Tetraiodo-L-thyronine4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanineD-ThyroxineDL-ThyroxinHenningL-3,5,3',5'-TetraiodothyronineL-T4L-ThyroxinL-ThyroxineLaevothyroxinumLevothroidLevothyroxinLevothyroxine sodiumLevothyroxinumLevoxylLT4O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosinePrestwick_548S-ThyroxineSynthroidT4TetraiodothyronineTetrametTHXThyratabsThyraxThyreoideumThyroxinThyroxinalThyroxine I 125Thyroxine iodineC15H11I4NO4776.87776.6866815252-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acidthyroxine51-48-9NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=OInChI=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)XUIIKFGFIJCVMT-UHFFFAOYSA-N 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.Phenylalanine and derivativesOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesAmino acids, peptides, and analoguesAromatic homomonocyclic compoundsAlpha amino acidsAmino acidsAmphetamines and derivativesAralkylaminesAryl iodidesCarbonyl compoundsCarboxylic acidsDiarylethersDiphenylethersHydrocarbon derivativesIodobenzenesMonoalkylaminesMonocarboxylic acids and derivativesO-iodophenolsOrganic oxidesOrganoiodidesOrganopnictogen compoundsPhenol ethersPhenoxy compoundsPhenylpropanoic acids2-halophenol2-iodophenol3-phenylpropanoic-acidAlpha-amino acidAmineAmino acidAmphetamine or derivativesAralkylamineAromatic homomonocyclic compoundAryl halideAryl iodideBenzenoidCarbonyl groupCarboxylic acidDiaryl etherDiphenyletherEtherHalobenzeneHydrocarbon derivativeIodobenzeneMonocarboxylic acid or derivativesMonocyclic benzene moietyOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganohalogen compoundOrganoiodideOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenolPhenol etherPhenoxy compoundPhenylalanine or derivativesPrimary aliphatic aminePrimary amine2-halophenola hormonean iodoaromatic compoundiodophenoliodothyroninenon-proteinogenic alpha-amino acidtyrosine derivativeSolidlogp1.15logs-4.94solubility8.98e-03 g/llogp3.73pka_strongest_acidic0.27pka_strongest_basic9.43iupac2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acidaverage_mass776.87mono_mass776.686681525smilesNC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=OformulaC15H11I4NO4inchiInChI=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)inchikeyXUIIKFGFIJCVMT-UHFFFAOYSA-Npolar_surface_area92.78refractivity126.79polarizability49.62rotatable_bond_count5acceptor_count4donor_count3physiological_charge0formal_charge0Tyrosine MetabolismSMP00006map00350Specdb::MsMs989051Specdb::MsMs989052Specdb::MsMs989053Specdb::MsMs1113359Specdb::MsMs1113360Specdb::MsMs1113361HMDB00248T44#<Reference:0x0000555674866620>#<Reference:0x00005556748661e8>#<Reference:0x0000555674866008>#<Reference:0x0000555674865ce8>#<Reference:0x0000555674865748>#<Reference:0x0000555674865388>#<Reference:0x00005556748650e0>#<Reference:0x0000555674864d48>#<Reference:0x0000555674864b18>#<Reference:0x00005556748648e8>#<Reference:0x0000555674864690>#<Reference:0x0000555674864410>#<Reference:0x00005556748641e0>#<Reference:0x0000555674857ee0>#<Reference:0x0000555674857d28>#<Reference:0x0000555674857b70>#<Reference:0x00005556748579b8>#<Reference:0x0000555674857800>#<Reference:0x0000555674857648>#<Reference:0x0000555674857490>Thyroxine-binding globulinP05543SERPINA7TransthyretinP02766TTRType I iodothyronine deiodinaseP49895DIO1Type II iodothyronine deiodinaseQ92813DIO2Type III iodothyronine deiodinaseP55073DIO3