1.0 2011-04-11 17:18:27 UTC 2015-10-09 22:30:38 UTC FDB021829 Levothyroxine The 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] (-)-Thyroxine 3,3',5,5'-Tetraiodo-L-thyronine 3,3',5,5''-tetraiodo-L-thyronine 3,5,3',5'-TETRAIODO-L-thyronine 3,5,3',5'-Tetraiodothyronine 3,5,3'5'-Tetraiodo-L-thyronine 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine D-Thyroxine DL-Thyroxin Henning L-3,5,3',5'-Tetraiodothyronine L-T4 L-Thyroxin L-Thyroxine Laevothyroxinum Levothroid Levothyroxin Levothyroxine sodium Levothyroxinum Levoxyl LT4 O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine Prestwick_548 S-Thyroxine Synthroid T4 Tetraiodothyronine Tetramet THX Thyratabs Thyrax Thyreoideum Thyroxin Thyroxinal Thyroxine I 125 Thyroxine iodine C15H11I4NO4 776.87 776.686681525 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid thyroxine 51-48-9 NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O 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) 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 derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic homomonocyclic compounds Alpha amino acids Amino acids Amphetamines and derivatives Aralkylamines Aryl iodides Carbonyl compounds Carboxylic acids Diarylethers Diphenylethers Hydrocarbon derivatives Iodobenzenes Monoalkylamines Monocarboxylic acids and derivatives O-iodophenols Organic oxides Organoiodides Organopnictogen compounds Phenol ethers Phenoxy compounds Phenylpropanoic acids 2-halophenol 2-iodophenol 3-phenylpropanoic-acid Alpha-amino acid Amine Amino acid Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Aryl halide Aryl iodide Benzenoid Carbonyl group Carboxylic acid Diaryl ether Diphenylether Ether Halobenzene Hydrocarbon derivative Iodobenzene Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organohalogen compound Organoiodide Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Phenol ether Phenoxy compound Phenylalanine or derivatives Primary aliphatic amine Primary amine 2-halophenol a hormone an iodoaromatic compound iodophenol iodothyronine non-proteinogenic alpha-amino acid tyrosine derivative Solid logp 1.15 ALOGPS logs -4.94 ALOGPS solubility 8.98e-03 g/l ALOGPS logp 3.73 ChemAxon pka_strongest_acidic 0.27 ChemAxon pka_strongest_basic 9.43 ChemAxon iupac 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid ChemAxon average_mass 776.87 ChemAxon mono_mass 776.686681525 ChemAxon smiles NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O ChemAxon formula C15H11I4NO4 ChemAxon 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) ChemAxon inchikey XUIIKFGFIJCVMT-UHFFFAOYSA-N ChemAxon polar_surface_area 92.78 ChemAxon refractivity 126.79 ChemAxon polarizability 49.62 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Tyrosine Metabolism SMP00006 map00350 Specdb::MsMs 989051 Specdb::MsMs 989052 Specdb::MsMs 989053 Specdb::MsMs 1113359 Specdb::MsMs 1113360 Specdb::MsMs 1113361 HMDB00248 T44 #<Reference:0x000055ac3ef84298> #<Reference:0x000055ac3ef84068> #<Reference:0x000055ac3ef83e38> #<Reference:0x000055ac3ef83c58> #<Reference:0x000055ac3ef83aa0> #<Reference:0x000055ac3ef837a8> #<Reference:0x000055ac3ef832d0> #<Reference:0x000055ac3ef82da8> #<Reference:0x000055ac3ef82a60> #<Reference:0x000055ac3ef828a8> #<Reference:0x000055ac3ef826f0> #<Reference:0x000055ac3ef82510> #<Reference:0x000055ac3ef82358> #<Reference:0x000055ac3ef821a0> #<Reference:0x000055ac3ef81fe8> #<Reference:0x000055ac3ef81e30> #<Reference:0x000055ac3ef81c78> #<Reference:0x000055ac3ef81ac0> #<Reference:0x000055ac3ef81908> #<Reference:0x000055ac3ef81750> Thyroxine-binding globulin P05543 SERPINA7 Transthyretin P02766 TTR Type I iodothyronine deiodinase P49895 DIO1 Type II iodothyronine deiodinase Q92813 DIO2 Type III iodothyronine deiodinase P55073 DIO3