L-thyroxine (CHEBI:18332)

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CHEBI:18332 - L-thyroxine

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ChEBI Name	L-thyroxine

ChEBI ID	CHEBI:18332

ChEBI ASCII Name	L-thyroxine

Definition	The L-enantiomer of thyroxine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:7663, CHEBI:45848, CHEBI:13177, CHEBI:21406

Supplier Information	ZINC000003938704

Download	Molfile XML SDF

more structures >>

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reading 35 atoms

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35 atoms created

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Wikipedia	License
Levothyroxine, also known as L-thyroxine, is a synthetic form of the thyroid hormone thyroxine (T4). It is used to treat thyroid hormone deficiency (hypothyroidism), including a severe form known as myxedema coma. It may also be used to treat and prevent certain types of thyroid tumors. It is not indicated for weight loss. Levothyroxine is taken orally (by mouth) or given by intravenous injection. Levothyroxine has a half-life of 7.5 days when taken daily, so about six weeks is required for it to reach a steady level in the blood. Side effects from excessive doses include weight loss, trouble tolerating heat, sweating, anxiety, trouble sleeping, tremor, and fast heart rate. Use is not recommended in people who have had a recent heart attack. Use during pregnancy has been found to be safe. Dosing should be based on regular measurements of thyroid-stimulating hormone (TSH) and T4 levels in the blood. Much of the effect of levothyroxine is following its conversion to triiodothyronine (T3). Levothyroxine was first made in 1927. It is on the World Health Organization's List of Essential Medicines. Levothyroxine is available as a generic medication. In 2022, it was the fourth most commonly prescribed medication in the United States, with more than 82 million prescriptions.
Read full article at Wikipedia

Formula

C15H11I4NO4

Net Charge

Average Mass

776.87006

Monoisotopic Mass

776.68669

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)/t12-/m0/s1

InChIKey

XUIIKFGFIJCVMT-LBPRGKRZSA-N

SMILES

N[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	antithyroid drug A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). thyroid hormone Any hormone produced by the thyroid gland mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). mitogen A chemical substance that encourages a cell to commence cell division, triggering mitosis. (via thyroxine )

Application(s):	antithyroid drug A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-thyroxine (CHEBI:18332) has role antithyroid drug (CHEBI:50671) L-thyroxine (CHEBI:18332) has role human metabolite (CHEBI:77746) L-thyroxine (CHEBI:18332) has role mouse metabolite (CHEBI:75771) L-thyroxine (CHEBI:18332) has role thyroid hormone (CHEBI:60311) L-thyroxine (CHEBI:18332) is a 2-halophenol (CHEBI:53291) L-thyroxine (CHEBI:18332) is a L-phenylalanine derivative (CHEBI:84144) L-thyroxine (CHEBI:18332) is a iodophenol (CHEBI:24863) L-thyroxine (CHEBI:18332) is a non-proteinogenic L-α-amino acid (CHEBI:83822) L-thyroxine (CHEBI:18332) is a thyroxine (CHEBI:30660) L-thyroxine (CHEBI:18332) is conjugate acid of L-thyroxine(1−) (CHEBI:60302) L-thyroxine (CHEBI:18332) is enantiomer of D-thyroxine (CHEBI:30659) L-thyroxine (CHEBI:18332) is tautomer of L-thyroxine zwitterion (CHEBI:58448)

Incoming	desiccated thyroid extract (CHEBI:9584) has part L-thyroxine (CHEBI:18332) L-thyroxine(1−) (CHEBI:60302) is conjugate base of L-thyroxine (CHEBI:18332) D-thyroxine (CHEBI:30659) is enantiomer of L-thyroxine (CHEBI:18332) L-thyroxine residue (CHEBI:90872) is substituent group from L-thyroxine (CHEBI:18332) L-thyroxine zwitterion (CHEBI:58448) is tautomer of L-thyroxine (CHEBI:18332)

IUPAC Name

L-thyroxine

Synonyms	Sources
3,3',5,5'-tetraiodo-L-thyronine	ChemIDplus
3,5,3',5'-TETRAIODO-L-THYRONINE	PDBeChem
3,5,3',5'-tetraiodo-L-thyronine	ChemIDplus
4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine	IUPAC
L-T₄	ChemIDplus
L-Thyroxine	KEGG COMPOUND
Levothyroxin	KEGG COMPOUND
levothyroxine	ChemIDplus
LT₄	ChEBI
O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine	PDBeChem
T4	KEGG COMPOUND
T₄	ChEBI

Manual Xrefs	Databases
2646	DrugCentral
3004	VSDB
C01829	KEGG COMPOUND
D08125	KEGG DRUG
DB00451	DrugBank
Levothyroxine	Wikipedia
LSM-5447	LINCS
T44	PDBeChem
View more database links

Registry Numbers	Types	Sources
2228515	Beilstein Registry Number	Beilstein
51-48-9	CAS Registry Number	KEGG COMPOUND
51-48-9	CAS Registry Number	ChemIDplus
7002831	Beilstein Registry Number	Beilstein

Citations

Last Modified

18 February 2021

CHEBI:18332 - L-thyroxine

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