Levothyroxine

Base Information

• Chemical Name: Levothyroxine
• CAS No.: 51-48-9
• Deprecated CAS: 587-29-1,587-30-4,7200-84-2,74-16-8,7488-70-2,1373931-44-2,1373931-44-2,587-30-4,7200-84-2,74-16-8,7488-70-2
• Molecular Formula: C15H11I4NO4
• Molecular Weight: 776.875
• Hs Code.: 29379000
• European Community (EC) Number: 200-221-4
• NSC Number: 757434
• UNII: Q51BO43MG4
• DSSTox Substance ID: DTXSID8023214
• Nikkaji Number: J4.118A
• Wikipedia: Levothyroxine
• Wikidata: Q773449
• NCI Thesaurus Code: C62080,C175725
• RXCUI: 10582,40144,1372638
• Pharos Ligand ID: YGYNAQAA9L6S
• Metabolomics Workbench ID: 37160
• ChEMBL ID: CHEMBL1624
• Mol file: 51-48-9.mol

Synonyms:3,5,3',5'-Tetraiodothyronine;Berlthyrox;Dexnon;Eferox;Eltroxin;Eltroxine;Euthyrox;Eutirox;L Thyrox;L Thyroxin beta;L Thyroxin Henning;L Thyroxine;L Thyroxine Roche;L-3,5,3',5'-Tetraiodothyronine;L-Thyrox;L-Thyroxin beta;L-Thyroxin Henning;L-Thyroxine;L-Thyroxine Roche;Lévothyrox;Levo T;Levo-T;Levothroid;Levothyroid;Levothyroxin Deladande;Levothyroxin Delalande;Levothyroxine;Levothyroxine Sodium;Levoxine;Levoxyl;Novothyral;Novothyrox;O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosine;O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine;Oroxine;Sodium Levothyroxine;Synthroid;Synthrox;T4 Thyroid Hormone;Thevier;Thyrax;Thyroid Hormone, T4;Thyroxin;Thyroxine;Tiroidine;Tiroxina Leo;Unithroid

Chemical Property of Levothyroxine

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 4.02E-14mmHg at 25°C
• Melting Point: 235 °C
• Refractive Index: 1.795
• Boiling Point: 576.306 °C at 760 mmHg
• PKA: 2.2(at 25℃)
• Flash Point: 302.339 °C
• PSA: 92.78000
• Density: 2.635 g/cm³
• LogP: 5.25760
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Dissolves in 4M ammonium hydroxide in Methanol at 50mg/ml
• Water Solubility.: insoluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 776.6867
• Heavy Atom Count: 24
• Complexity: 420

Purity/Quality:

98%, ^*data from raw suppliers

Thyroxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 40-39/23/24/25-23/24/25-11
• Safety Statements: 22-24/25-36-45-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)CC(C(=O)O)N
• Isomeric SMILES: C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)C[C@@H](C(=O)O)N
• Recent ClinicalTrials: The Effect of Thyroid Hormone Therapy on Muscle Mass and Function in Older Adults With Subclinical Hypothyroidism
• Recent EU Clinical Trials: Hormones and Muscle
• Recent NIPH Clinical Trials: Effects of replacement therapy on indices of atherosclerosis in subclinical hypothyroidism
• Description: L-Thyroxine is a synthetic form of the thyroid hormone thyroxine. In vivo, L-thyroxine (0.9 and 2.7 μg) inhibits synthesis and release of thyrotropin induced by thyrotropin-releasing hormone from the anterior pituitary in mice. It also reverses decreases in levels of circulating thymic serum factor (FTS) and the number of T rosette-forming cells in an old age-induced mouse model of hypothyroidism. Formulations containing L-thyroxine have been used in the treatment of hypothyroidism.
• Uses: antihypercholesterimic, thyromimetic One of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroi d hormone, but has been used to treat hyperlipidemia. Thyroxine is one of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroid hormone, but has been used to treat hyperlipidemia.
• Indications: Effects of this drug depend heavily on dosage. In small doses, levothyroxine exhibits anabolic action. In medium doses, it stimulates growth and development of tissue, metabolism of protein, fats, and carbohydrates, increases functional activity of central nervous and cardiovascular systems, as well as kidneys and liver. In large doses, it slows the thyrotropic activity of the hypophysis and suppresses thyroid gland production. Levothyroxine is used for hypothyroidism, myxedema, thyrotoxicosis, erythyroid conditions, and cretinism.
• Therapeutic Function: Thyroid hormone

Technology Process of Levothyroxine

There total 34 articles about Levothyroxine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

L-thyroxine, sodium salt hexahydrate → L-thyroxine (51-48-9,24486-40-6)

Guidance literature:

With hydrogenchloride; In methanol; dimethyl sulfoxide;

Reference yield: 94.0%

3,5-diiodo-l-tyrosine (300-39-0) + 5,7-diiodo-1-oxaspiro[2.5]octa-4,7-dien-6-one → L-thyroxine (51-48-9,24486-40-6)

Guidance literature:

In N,N-dimethyl-formamide; at 24 ℃; for 16h; 0.2 M borate buffer, pH 8.0 (add. of 0.1 M NaOH);

DOI:10.1016/S0040-4039(97)01665-1

Reference yield: 91.2%

3,3′-diiodothyronine (70-40-6) → L-thyroxine (51-48-9,24486-40-6)

Guidance literature:

3,3′-diiodothyronine; With methylamine; In methanol; at 25 - 30 ℃;

With iodine; In methanol; at -8 - 0 ℃;

With potassium dihydrogenphosphate; sodium hydrogensulfite; In methanol; at 15 - 20 ℃;

upstream raw materials:

3,5-diiodo-l-tyrosine

3,5-diiodo-L-thyronine

N-acetyl-3,5-diiodo-L-tyrosine

iodoacetamide

Downstream raw materials:

O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine

N-chloroacetyl-3,5,3',5'-tetraiodo-L-thyronine

(S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-propionic acid methyl ester

L-3,3',5'-triiodothyronine

Refernces

• 1、 -. "Liquid levothyroxine formulations". . . Retrieved 2016/06/13.
• 2、 -. "A PROCESS FOR PREPARATION OF LEVOTHYROXINE AND SALTS THEREOF". Page/Page column 14. . Retrieved 2015/11/30.