Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:35:39 UTC
Update Date2024-10-11 02:18:49 UTC
Metabolite IDMMDBc0000337
Metabolite Identification
Common NameThyroxine
DescriptionThyroxine (3,5,3′,5′-tetraiodothyronine) or T4 is one of two major hormones derived from the thyroid gland, the other being triiodothyronine (T3). The major form of thyroid hormone in the blood is thyroxine (T4), which has a longer half-life than T3. In humans, the ratio of T4 to T3 released into the blood is approximately 14:1. T4 is converted to the active T3 (three to four times more potent than T4) within cells by enzymes known as deiodinases (5′-iodinase). Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Iodine is critical to the synthesis of thyroxine and other thyroid hormones. Through a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues found in the thyroglobulin protein, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one molecule of MIT and one molecule of DIT produces triiodothyronine. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles where thyroxine is produced. If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in a condition called goitre. More specifically, the lack of thyroid hormones will lead to decreased negative feedback on the pituitary gland, leading to increased production of thyroid-stimulating hormone, which causes the thyroid to enlarge, leading to goitre. Thyroxine can be peripherally de-iodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism. Thyroid hormones function via a well-studied set of nuclear receptors, termed the thyroid hormone receptors. They act on nearly every cell in the body. In particular, thyroid hormones act to increase the basal metabolic rate, affect protein synthesis, help regulate long bone growth (synergy with growth hormone) and neural maturation, and increase the body's sensitivity to catecholamines (such as adrenaline) by permissiveness. The thyroid hormones are essential to proper development and differentiation of all cells of the human body. These hormones also regulate protein, fat, and carbohydrate metabolism, affecting how human cells use energetic compounds. They also stimulate vitamin metabolism. Numerous physiological and pathological stimuli influence thyroid hormone synthesis. Levothyroxine, a manufactured form of thyroxine, was the most prescribed medication in the United States with more than 114 million prescriptions.
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
Molecular FormulaC15H11I4NO4
Average Mass776.87
Monoisotopic Mass776.686681525
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
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-/m0/s1
InChI KeyXUIIKFGFIJCVMT-LBPRGKRZSA-N