Levothyroxine sodium monohydrate

Base Information

• Chemical Name: Levothyroxine sodium monohydrate
• CAS No.: 55-03-8
• Deprecated CAS: 61333-06-0
• Molecular Formula: C15H10I4NNaO4
• Molecular Weight: 798.856
• Hs Code.: 2937909000
• European Community (EC) Number: 200-221-4,685-634-1
• UNII: B82379R9W0
• Wikidata: Q27107209
• NCI Thesaurus Code: C888,C175725
• RXCUI: 40144,1372638
• ChEMBL ID: CHEMBL2103741
• Mol file: 55-03-8.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 sodium monohydrate

Chemical Property:

• Melting Point: 207-210 (dec.)(lit.)
• Boiling Point: 576.3 °C at 760 mmHg
• Flash Point: 302.3 °C
• PSA: 141.76000
• Density: d420 2.381
• LogP: 3.60140
• Storage Temp.: 2-8°C
• Solubility.: cell culture medium: 0.1 mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 816.6792
• Heavy Atom Count: 26
• Complexity: 426

Purity/Quality:

98%min ^*data from raw suppliers

ThyroxineSodiumSalt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

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.O.[Na+]
• Isomeric SMILES: C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)C[C@@H](C(=O)[O-])N.O.[Na+]
• Recent ClinicalTrials: Study of XP-8121 For the Treatment of Adult Subjects With Hypothyroidism
• Recent EU Clinical Trials: A national randomized placebo-controlled double-blind multicenter trial of
• Uses: 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: Levothyroxine sodium (Levothroid, Synthroid, Levoxine) is the sodium salt of the naturally occurring levorotatory isomer of T4. It is the preparation of choice for maintenance of plasma T4 and T3 concentrations for thyroid hormone replacement therapy in hypothyroid patients. It is absorbed intact from the gastrointestinal tract, and its long half-life allows for convenient oncedaily administration. Since much of the T4 is deiodinated to T3, it is usually unnecessary to use more expensive preparations containing both T4 and T3.The aim is to establish euthyroidism with measured serum concentrations of T4, T3, and TSH within the normal range. The TSH-suppressive effects of exogenous T4 also prove useful in removing the stimulatory effects of TSH on the thyroid gland in the management of simple nonendemic goiter, chronic thyroiditis, and TSHdependent thyroid carcinoma.
• Therapeutic Function: Thyroid hormone
• Clinical Use: Liothyronine sodium occurs in vivo together withlevothyroxine sodium; it has the same qualitative activitiesas thyroxine but is more active. It is absorbed readily fromthe gastrointestinal tract, is cleared rapidly from the bloodstream,and is bound more loosely to plasma proteins than isthyroxine, probably because of the less acidic phenolic hydroxylgroup.Its uses are the same as those of levothyroxine sodium,including treatment of metabolic insufficiency, male infertility,and certain gynecological disorders.

Technology Process of Levothyroxine sodium monohydrate

There total 14 articles about Levothyroxine sodium monohydrate 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: 98.0%

L-thyroxine (51-48-9,24486-40-6) → L-thyroxine sodium (55-03-8)

Guidance literature:

With sodium carbonate; In water; Reflux;

Reference yield: 92.0%

O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine disodium salt → L-thyroxine sodium (55-03-8)

Guidance literature:

O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine disodium salt; With sodium hydroxide; In water; at 25 - 30 ℃; pH=~ 12 - 13;

With hydrogenchloride; In water; pH=2 - 3; Product distribution / selectivity;

Reference yield: 90.0%

L-thyroxine disodium → L-thyroxine monosodium (55-03-8)

Guidance literature:

L-thyroxine disodium; With pyrographite; sodium hydroxide; sodium sulfite; In water; at 25 - 30 ℃; for 0.25h;

With sodium carbonate; acetic acid; In water; at 15 - 80 ℃; for 3.5h; Product distribution / selectivity;

upstream raw materials:

L-thyroxine

3,5-diiodo-l-tyrosine

4,4'-dimethoxydiphenyliodonium iodide

2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid

Downstream raw materials:

L-thyroxine

Refernces

• 1、 -. "Preparation method of levothyroxine sodium". Paragraph 0009; 0037; 0038. . Retrieved 2019/06/05.
• 2、 -. "A PROCESS FOR PREPARATION OF LEVOTHYROXINE AND SALTS THEREOF". Paragraph 12; 13. . Retrieved 2015/11/30.