FComEx: Levothyroxine (PC000423)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:37 UTC

Update date

2017-01-19 02:36:23 UTC

FoodComEx ID

PC000423

FoodDB Record

FDB021829

Chemical Information

Name

Levothyroxine

Description

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]

CAS Number

51-48-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(-)-Thyroxine	HMDB
3,3',5,5'-Tetraiodo-L-thyronine	ChEBI
3,3',5,5''-tetraiodo-L-thyronine	HMDB
3,5,3',5'-TETRAIODO-L-thyronine	ChEBI
3,5,3',5'-Tetraiodothyronine	HMDB
3,5,3'5'-Tetraiodo-L-thyronine	HMDB
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine	ChEBI
D-Thyroxine	HMDB
DL-Thyroxin	HMDB
Henning	HMDB
L-3,5,3',5'-Tetraiodothyronine	HMDB
L-T4	ChEBI
L-Thyroxin	HMDB
L-Thyroxine	ChEBI
Laevothyroxinum	HMDB
Levothroid	HMDB
Levothyroxin	ChEBI
Levothyroxine sodium	HMDB
Levothyroxinum	HMDB
Levoxyl	HMDB
LT4	ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine	ChEBI
Prestwick_548	HMDB
S-Thyroxine	manual
Synthroid	HMDB
T4	ChEBI
Tetraiodothyronine	HMDB
Tetramet	HMDB
THX	HMDB
Thyratabs	HMDB
Thyrax	HMDB
Thyreoideum	HMDB
Thyroxin	HMDB
Thyroxinal	HMDB
Thyroxine I 125	HMDB
Thyroxine iodine	HMDB

Chemical Formula

C15H11I4NO4

IUPAC name

2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

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)

InChI Key

XUIIKFGFIJCVMT-UHFFFAOYSA-N

Isomeric SMILES

NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O

Average Molecular Weight

776.87

Monoisotopic Molecular Weight

776.686681525

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents